Supernatural binge guide: 75 essential episodes to watch

In October, Supernatural will launch its 15th and final season. For those of you looking to join the #SPNFamily without watching all 307 episodes — or for anyone who wants a refresher course that will take slightly less time than a full binge — EW has rounded up the 75 essential Supernatural episodes. These are the episodes responsible for some of the show’s biggest stories, twists, turns, and memorable hours. That’s not to say they’re the 75 best hours — you can find our favorites here. But it is to say that if you watched these and only these, you’d get a good sense of what this show is, how the mythology has played out, and why so many people love it — and just in time to watch the final 20 episodes, which premiere Thursday, Oct. 10 at 8 p.m. ET on The CW.

 cleanString caption

“Pilot” (Season 1, Episode 1)

Whether you’ve never seen Supernatural before or you’re about to start your millionth re-watch, no binge would be complete without the episode that started it all. Written by Eric Kripke and directed by pilot-whisperer David Nutter, the first hour of the series sets up everything you need to know (or remember) about who Sam and Dean are, why they do what they do, and why we care about them so much.

“Bloody Mary” (Season 1, Episode 5)

Back in the early seasons (and especially the first one), Supernatural used to be a lot scarier in the procedural stories it told. This hour is the perfect example of the kind of classic horror that used to dominate the show, as it explored the urban legend Bloody Mary to terrifying results.

“Faith” (Season 1, Episode 12)

The first appearance of a Reaper in this episode is absolutely essential to the boys’ history, as they’ll come into contact with these harbingers of Death (with a capital D) time and time again — usually with heartbreaking consequences.

“The Benders” (Season 1, Episode 15)

Supernatural is a story about two brothers saving people and hunting things — the family business. But what happens when the things killing people are just … people? This chilling twist brilliantly subverts everything the boys previously thought they knew about the world and what goes bump in the night.

“Devil’s Trap” (Season 1, Episode 22)

You can always rely on Supernatural to deliver one hell of a finale. The introduction of fan-favorite Bobby, John’s return, heartbreaking twists, and that pulse-stopping cliffhanger make this not only one of the best episodes of this season but also one of the best Supernatural episodes of all time.

 cleanString caption

“In My Time of Dying” (Season 2, Episode 1)

Supernatural giveth and Supernatural taketh away. A beloved character’s return is made all the more heartbreaking as he’s ripped away from the boys — and us — so soon. We’ll never forgive Azazel for a lot of things, but this one hurts the most, especially since it’s the first time (but hardly the last) that we almost lose one of the boys as Dean comes this close to dying.

“Croatoan” (Season 2, Episode 9)

One of the most important arcs in Supernatural history begins in this ominous hour that tells the story of the lost colony of Roanoke through a supernatural lens. It will be a long time before answers come but this episode is essential in the story of Sam’s complicated DNA.

“Tall Tales” (Season 2, Episode 15)

When the Trickster was first introduced, his powers of reality manipulation were already impressive. But fans had no idea just how powerful he truly is. That would come three seasons later.

 cleanString caption

“Hollywood Babylon” (Season 2, Episode 18)

By this point, Supernatural has proven its horror expertise. But what about comedy? The show kicks off its beloved tradition of meta episodes as Sam and Dean take a case on a haunted film set where every note given by the producer is a critique that had been leveled at Supernatural by the network/studio for the past season and a half.

“What Is and What Should Never Be” (Season 2, Episode 20)

Out of both Winchester brothers, it’s common knowledge at this point that Sam has a different vision for his life, one that doesn’t involve living on the road and hunting. But what does Dean’s dream for a life without hunting look like? This peek into his mind offers a deeper look at his fantasy — and how much he’s willing to sacrifice.

“All Hell Breaks Loose (Part 1)” (Season 2, Episode 21)

You thought Supernatural killed it with its first season finale? Season 2 is all, “Hold my beer.” Both hours of this rare two-part finale are necessary viewing for any binge-watch. Azazel’s half-demon champions’ brutal fight to the death in the first episode ends in complete disaster. And it’s only half of the finale!

“All Hell Breaks Loose (Part 2)” (Season 2, Episode 22)

How can Supernatural go on after death rocks the boys? Easy: fans see the first (of many) rash deals to trade one life for another, thanks to a crossroads demon. The clock starts ticking: one year until hell becomes home for one of the Winchesters. Plus, the conclusion of both Yellow Eyes and John Winchester’s stories make this finale crucial to the overall history of Supernatural.

“The Magnificent Seven” (Season 3, Episode 1)

Hell literally broke loose at the end of season 2, and Supernatural’s third season kicks off with a clever case spinning out of that finale: the seven deadly sins are now roaming the Earth once more. In the premiere, the brothers have to track down the sins, which have taken the form of demons and are causing all kinds of chaos. Hanging over all of this, though, is the knowledge that Dean only has a year to live because of the deal he made. This episode also marks the introduction the demon Ruby, here played by a pre-Arrow Katie Cassidy Rodgers.

 cleanString caption

“Bad Day at Black Rock” (Season 3, Episode 3)

Sam and Dean chase after a thief named Bella (The Walking Dead’s Lauren Cohan), who hired some men to steal a rabbit’s foot from their father’s storage. Unfortunately, the occult object is pretty dangerous. If you have it, you’re blessed with good luck; however, if (and when) you lose it, you’ll suffer a string of bad luck that takes the form of hilarious Rube Goldbergian-like set-pieces that ultimately lead to your death. This is one of the rare instances where Supernatural fully embraces slapstick humor, which makes it stand out from the rest.

“Mystery Spot” (Season 3, Episode 11)

When Sam finds himself stuck in a time loop, he’s forced to watch his brother die over and over again. To this day, “Mystery Spot” remains one of Supernatural’s best and most inventive episodes because it uses a simple and gimmicky premise to dig into the brothers’ relationship and breaks away from Supernatural’s usual formula.

“Ghostfacers” (Season 3, Episode 13)

“Ghostfacers” is like every other “Sam and Dean investigate a haunted house” episode, except in one major way: It’s shot almost entirely like a ghost-hunting reality show. See, when Sam and Dean travel to Wisconsin to check out the home of a leap year-loving ghost, they cross paths with amateur hunters Harry Spangler (Travis Wester) and Ed Zeddmore (A. J. Buckley), who are also there filming the pilot for their new show. Thus, we get a hilarious spin on a typical case.

“No Rest for the Wicked” (Season 3, Episode 16)

The clock is starting to run out on Dean’s time on Earth. In a last-ditch effort to prevent him from going to hell, Sam and Dean go into their final confrontation with Lillith. You can probably guess what happens after that…

“Lazarus Rising” (Season 4, Episode 1)

One word: Angels. The introduction of Castiel not only changes the makeup of the series as a whole (what used to be a two-hander with just the Winchester boys is now a trio) but also alters the mythology forever. Angels are real, God exists, and He’s got work for Dean to do. This episode is an absolute game-changer.

 cleanString caption

“In the Beginning” (Season 4, Episode 3)

Time travel allows Dean to meet a young Mary and John and get crucial details on their family history with Yellow Eyes, a.k.a. the demon Azazel. It’s also the first time we realize that there’s a reason why Supernatural’s version of the biblical creatures don’t wear halos.

“Yellow Fever” (Season 4, Episode 6)

One of the most GIF-ed moments of Supernatural (and there are many, so that’s saying something) comes from this episode when Dean, infected with a ghostly sickness that escalates his fear to fatal levels, lets out an instantly iconic scream … all because of a kitten.

 cleanString caption

“I Know What You Did Last Summer” (Season 4, Episode 9)

After eight episodes of mystery surrounding what happened to Sam all those months that Dean was in Hell, we finally get the real story told via flashbacks. It helps explain why Sam trusts Ruby so much and also shows why Dean ultimately decides to trust her as well. Plus, the ominous easter egg reveal that Dean knows major demon Alistair from his time in Hell will prove important in later episodes (and Anna’s introduction will also be important, although it’s not clear why just yet).

“Heaven and Hell” (Season 4, Episode 10)

Angels and demons fighting it out makes this hour epic. But it’s really the emotional brother moment at the very end when Dean confides in Sam about his time in Hell that makes this episode truly essential viewing. It’s one of the best “Sam and Dean having a conversation on the side of the road after working a case” scenes of the entire series.

“The Monster at the End of This Book” (Season 4, Episode 18)

The introductory hour of Chuck Shurley and the Supernatural books is not only a hilarious meta episode worth watching just for the laughs, but it also holds more importance to the larger mythology of Supernatural than anyone realized (for years!). Honorable mention: While it didn’t make this essential episodes list, a good follow-up to this episode is season 5’s “The Real Ghostbusters,” as both Chuck and the Supernatural books make a glorious return in the form of a Supernatural convention — a brilliant love letter to the real-world Supernatural convention circuit that helped catapult this show to international levels of fame.

“When the Levee Breaks” (Season 4, Episode 21)

Sam’s consumption of demon blood has been a slow-burn story that finally comes to a head in the season’s penultimate hour. The impending apocalypse actually pales in comparison to the knock-down, drag-out fight between Sam and Dean that ends in absolute disaster.

 cleanString caption

“Lucifer Rising” (Season 4, Episode 22)

You’d think the apocalypse coming to fruition would be the headline here, but actually it’s who is behind it that’s truly the shocker. Turns out that Sam and Dean have been manipulated from the start, and they’ve got a much bigger part to play in the end of the world than they ever realized. It all leads up to season 5, a.k.a. creator Eric Kripke’s original idea for how the show should end.

“Sympathy for the Devil” (Season 5, Episode 1)

If the season 4 finale was all about Lucifer rising, this is the true beginning of his story on the show — as well as the introduction of Mark Pellegrino — and it’s not something you want to miss as both Lucifer and Pellegrino will be integral parts of the series moving forward.

“Good God, Y’all” (Season 5, Episode 2)

You can’t have the apocalypse without the Four Horsemen, and this episode serves as a wonderfully constructed hour that introduces one of those key players. (Hint: He loves chaos.)

“The End” (Season 5, Episode 4)

One of the series’ strongest hours gives Dean a glimpse into a potential future reality. Aside from it being a highly creative episode of the series, it also features notable performances from both Jensen Ackles — who plays opposite himself — and Jared Padalecki (in a white suit).

 cleanString caption

“Changing Channels” (Season 5, Episode 8)

Leave it to the Trickster to help create one of the show’s most memorable meta episodes in which he sends the boys to various alternate realities, all of which mirror well-known television shows. (Grey’s Anatomy, anyone?) But all fun aside, this episode also includes a crucial twist that we won’t spoil here.

“Abandon All Hope” (Season 5, Episode 10)

Welcome to an incredibly intense and highly emotional hour as Sam and Dean team up with their closest allies to try and take down Lucifer. Spoiler: Things don’t go to plan and not everyone makes it out alive.

“The Song Remains the Same” (Season 5, Episode 13)

Sam and Dean take a trip back to 1978 and come face-to-face with a young John and Mary Winchester. But more importantly, the archangel Michael makes his debut and asks to have a chat with Dean.

 cleanString caption

“Point of No Return” (Season 5, Episode 18)

The show’s 100th hour includes quite a few major plot points for the series’ overall arc, including Dean’s confrontation with Zachariah and a big decision on the part of Adam, the Winchester half-brother.

“Hammer of the Gods” (Season 5, Episode 19)

An all-around great episode introduces a number of different gods and ends with a brother-on-brother showdown between Lucifer and Gabriel.

“Two Minutes to Midnight” (Season 5, Episode 21)

There’s a lot to love in this episode, but nothing tops one of the greatest entrances in the show’s history: Everyone, meet Death.

“Swan Song” (Season 5, Episode 22)

Eric Kripke’s final episode as showrunner — and the end of his supposed five-year plan — sees Michael and Lucifer go toe-to-toe in the series’ finest hour … thus far.

“Weekend at Bobby’s” (Season 6, Episode 4)

Ackles makes his directorial debut on Supernatural with this episode, which answers a question you probably had at the back of your mind: What does Bobby do when he’s not aiding the boys? Well, it turns out he conducts research for his own problems, works with other hunters around the country, and handles whatever goes bump in the night in his neck of the woods. Jim Beaver has long been an asset to the show as Bobby and he makes the most of his spotlight hour.

 cleanString caption

“The French Mistake” (Season 6, Episode 15)

Odds are if someone has tried to convince you to watch this show, they’ve mentioned this bold and delightfully meta episode. In order to protect the boys from a band of angels trying to kill them, the angel Balthazar shatters the fourth wall and sends them to an alternate reality where they’re actually actors named Jared Padalecki and Jensen Ackles who play Sam and Dean Winchester on a show called Supernatural. Confused? Very few live-action shows would ever attempt something as daring and experimental as this, and that’s why fans love this episode oh so much.

“The Man Who Would Be King” (Season 6, Episode 20)

Told entirely from Castiel’s perspective, the sad antepenultimate episode of the season reveals exactly what our favorite angel has been up to all season — from his role in Sam’s resurrection to the genesis of Heaven’s civil war, and his uneasy partnership with Crowley — and puts a strain on his relationship with Dean.

“The Man Who Knew Too Much” (Season 6, Episode 22)

Heaven’s civil war comes to a dramatic conclusion in the season 6 finale, which also sees the Winchester brothers face off with Castiel, and Sam confront everything he did while soulless. You hate to see it, but you love it — especially because the episode opens a door to the hitherto unseen Purgatory, which has drastic consequences going forward.

“Death’s Door” (Season 7, Episode 10)

There aren’t many season 7 episodes that we consider a “must,” but for Bobby fans, this most certainly fits the mold. And that’s all we can say about that.

 cleanString caption

“The Girl With the Dungeons and Dragons Tattoo” (Season 7, Episode 20)

All you need to know about this episode is that it’s important because it introduces Charlie, and Charlie is VERY important.

“Survival of the Fittest” (Season 7, Episode 23)

The season 7 finale puts an end to the Leviathan story and launches the show — as well as Dean and Castiel — in an entirely new direction.

“We Need to Talk About Kevin” (Season 8, Episode 1)

Dean’s shocking friendship with a new character after his time in Purgatory adds a complex layer to his philosophy on trusting “monsters” (something that he’d always been strictly black-and-white on before). This premiere is also incredibly important in establishing one of the few unforgivable acts in Sam and Dean’s relationship and delivering one of the most heartbreaking moments of the series.

“Trial and Error” (Season 8, Episode 14)

A lot of season 8 is filler, but what’s most important boils down to the mission to close the gates of Hell, locking in all demons before they can do the same to Heaven and angels. Thanks to prophet Kevin translating the instructions for the three trials to close the gates, Sam and Dean must complete the first trial: killing a Hellhound. Get ready to see the most amazing pair of glasses on the Winchesters along with one of the coolest action scenes yet on the show.

 cleanString caption

“Sacrifice” (Season 8, Episode 23)

It’s an understatement to say that Supernatural knows how to craft a brilliant finale. But nothing tops the final image of season 8. It’s both figuratively and literally beautiful as the brothers again choose each other over the greater good, again with disastrous consequences. Bonus: Crowley’s impassioned speech when Sam almost cures him of being a demon is one of the character’s best moments.

“I Think I’m Going to Like It Here” (Season 6, Episode 1)

With Sam literally on Death’s door, Dean makes a risky deal to save his brother’s life yet again, because there’s nothing these boys won’t do for each other. Meanwhile, Castiel adjusts to life as a human, which isn’t as easy as it seems.

“Holy Terror” (Season 9, Episode 9)

One of Sam and Dean’s allies perishes at the hands of Ezekiel, who turns out not to be who he says he is.

“First Born” (Season 9, Episode 11)

Meet Cain (Timothy Omundson), you know, of Cain and Abel. Dean crosses paths with history’s first murderer when he and Crowley go searching for the one weapon to kill Abaddon, a Knight of Hell. Unfortunately, the weapon they need, the First Blade, can only be used if Dean agrees to take the Mark of Cain, which comes with dire consequences that affect the show for multiple seasons to come.

“Do You Believe in Miracles” (Season 9, Episode 23)

Sam and Dean Winchester hunt demons. That’s their thing. Unfortunately, in their climactic fight against Metatron, who’s trying become the new God, one of them becomes the very thing they hate, pushing the show into uncharted territory.

“Soul Survivor” (Season 10, Episode 3)

Demon Dean doesn’t last long, and it’s the final hour that deserves attention as he comes face-to-face with Sam for the brutal, chill-inducing confrontation in the Men of Letters bunker. And keep your eye on that red-haired woman in the final scene as she will ultimately become an important character in the Supernatural universe.

 cleanString caption

“Fan Fiction” (Season 10, Episode 5)

The monumental 200th episode is another whimsical foray into meta storytelling as the boys encounter a high school production based on Chuck Shurley’s books (which are based on their lives). There are so many incredible easter eggs in this hour along with hilarious and touching musical tributes to the show. It’s a standalone episode but still delivers a game-changing shock in the final moment, as Supernatural seems to confirm a long-believed rumor with a cameo that no one saw coming.

“The Executioner’s Song” (Season 10, Episode 14)

A season and a half has led to this moment: Dean and Cain’s final battle. It’s also a major turning point for Crowley, who has become “the Winchesters’ lap dog,” according to his mother Rowena and is no longer fit to be the King of Hell after Dean successfully manipulates him.

“Dark Dynasty” (Season 10, Episode 21)

It may not be enjoyable, but this episode contains one of the biggest (and most hated among fans) deaths in Supernatural history.

“The Prisoner” (Season 10, Episode 22)

There are so many reasons why this is essential viewing: it’s the aftermath of an important character’s death. It features the culmination of Crowley and Rowena’s toxic mother/son relationship. And it sees Dean nearly kill someone close to him as he gives in to the darkness of the Mark of Cain.

 cleanString caption

“Brother’s Keeper” (Season 10, Episode 23)

This finale has everything. Another epic season-ending image, another heart wrenching brother-bonding moment as they choose each other over the fate of the world, and another shocking piece of mythology subverted. The shocks just keep on coming.

“Out of the Darkness, Into the Fire” (Season 11, Episode 1)

The season 11 premiere introduces a new, very powerful face into the mix: Amara, who will come to play a major role in the season (and potentially more).

“Baby” (Season 11, Episode 4)

Eleven seasons in and the show delivers one of its best hours with this episode, which is told entirely from the perspective of the boys’ 1967 Chevrolet Impala.

“Don’t Call Me Shirley” (Season 11, Episode 20)

Chuck is back and he’s … writing an autobiography? After years of speculation, this episode provides multiple answers surrounding Chuck’s identity and what he’s been up to.

“All in the Family” (Season 11, Episode 21)

Amara goes head-to-head with Lucifer in this episode, but here’s the twist: Lucifer is now in Castiel’s vessel. In other words, meet Cassifer.

“We Happy Few” (Season 11, Episode 22)

It’s the brother-sister showdown we’ve been waiting for as Chuck finally tells Amara why he locked her away all those years ago.

 cleanString caption

“Alpha and Omega” (Season 11, Episode 23)

The conclusion of the Chuck-Amara storyline isn’t the show’s strongest finale, but it does include crucial information for future seasons. Plus, there’s a very surprising return that will change everything for Sam and Dean.

“Keep Calm and Carry On” (Season 12, Episode 1)

The season 12 premiere is all about a major character return and the introduction of this season’s villains, the British Men of Letters.

“Stuck in the Middle (With You)” (Season 12, Episode 12)

Another creative hour, this episode tells a monster-of-the-week story Reservoir Dogs-style.

 cleanString caption

“All Along the Watchtower” (Season 12, Episode 23)

In terms of the show’s mythology, this episode cannot be missed as it involves the introduction of the Apocalypse World — where Sam and Dean were never born — a major character death (or two), and the birth of a Nephilim.

“Lost and Found” (Season 13, Episode 1)

Lucifer’s son Jack was born in the season 12 finale but instantly became a teenager. It’s not until the season 13 premiere, however, that fans get to see him for the first time with the reveal that while his body aged, his mind did not. That makes his limitless power even more dangerous, as he’s basically a baby with no knowledge of the world or his place in it. Thankfully he’s got Sam, Dean, and Castiel as his surrogate fathers — talk about an upgrade from Lucifer.

“The Big Empty” (Season 13, Episode 4)

After 13 years, there’s not much supernatural real estate that this series hasn’t tackled. But it’s not until this episode that the show attempts to explain what happens to angels and demons after they’re killed through the lens of deceased killed Castiel — after Jack unknowingly uses his powers to wake him up. Meet: The Big Empty.

“Advanced Thanatology” (Season 13, Episode 5)

Castiel’s return in this episode is big, but it’s actually Billie’s level up from Reaper to Death that makes this hour essential viewing. Plus, Dean’s willingness to literally kill himself shows just how dire things have gotten for him after many, many years of losing.

 cleanString caption

“Scoobynatural” (Season 13, Episode 16)

This epic animated crossover with Scooby-Doo deserves to be watched over and over … and over … and over …

“Unfinished Business” (Season 13, Episode 20)

Never trust a Trickster. If there’s one lesson that Supernatural’s Gabriel has taught over the years, it’s that one. But Sam and Dean constantly have to relearn it every time Gabriel comes back into play, and this time, they learn the true story about his history, his “death,” and his identity. This episode is the perfect companion to season 5’s “Hammer of the Gods.”

“Beat the Devil” (Season 13, Episode 21)

Years and countless death scenes still don’t make watching a Winchester die any easier. And this episode’s bloody, violent, and sudden death scene ranks as one of the most brutal ways a Winchester has died yet. Supernatural went full gore for this one, earning its legacy as an essential episode.

“Let the Good Times Roll” (Season 13, Episode 23)

It took seven seasons but this finale finally delivers payoff for an idea first introduced back in season 4 … with horrible consequences. This episode proves that Supernatural isn’t above playing the long game with Chekhov’s gun.

“Nihilism” (Season 14, Episode 10)

Come for the very metal episode name, stay to watch Ackles’ best performance as Michael-possessing-Dean.

 cleanString caption

“Lebanon” (Season 14, Episode 13)

It’s the reunion you’ve been waiting for: Jeffrey Dean Morgan returns as John Winchester in Supernatural’s 300th episode. Watching Sam, Dean, John, and Mary share a meal together after all these years will definitely leave you in need of some tissues.

“Absence” (Season 14, Episode 18)

Supernatural pays tribute to another one of its fallen hunters as Jack spins further out of control and becomes even more estranged from the Winchesters.

“Moriah” (Season 14, Episode 20)

God is back in the house! The question of “how much God actually cares about his creations” has hung over the show since angels and the apocalypse were first introduced in season 4. Now, the show has finally decided to answer that question and deliver one hell of a twist as Sam and Dean race to stop Jack.

Related content:

Jensen Ackles and Jared Padalecki star as the Winchester brothers, hellbent on battling the paranormal forces of evil.

Episode Recaps

The Playboy Mansion, Quentin Tarantinos kitchen, and more behind-the-scenes secrets from the stars of Once Upon a Time in Hollywood

To celebrate Quentin Tarantino‘s ninth (and, as he’s said, penultimate) film, Entertainment Weekly gathered the writer-director and three of Once Upon a Time in Hollywood‘s stars for an exclusive roundtable interview. Watch (and read) for behind-the-scenes secrets about the highly-anticipated movie straight from Brad Pitt, Leonardo DiCaprio, and Margot Robbie

ENTERTAINMENT WEEKLY: Quentin, were you always intending for this to be basically a valentine to Los Angeles?

QUENTIN TARANTINO: Yes, it was. I grew up in Los Angeles, I love it. I love it the way that the only people who truly love it are the people who live it the right way, are the people who grew up here and the people who know it.

BRAD PITT: Not true, not true! That does not have to be true!

TARANTINO: No, you can love it in your own way! But not the way we do. Not the way me and Leo do. But the thing is — especially when it came to 1969 — I was like between six and seven years old. And so the film became a big memory piece. And a big part of my memory of Los Angeles at that time is being in the car with my stepfather. Being in the car with my mom. And driving around listening to the radio all the time. And how we listened to the radio back then, which is different than the way we listen to the radio now, where you just kept it on one station. You didn’t move it around looking for songs.

I remember the bus stops advertising the rerun shows that were on the local television stations and the movie posters and the, you know, RC Cola billboards. That’s what I remember. In fact, my stepfather drove a Karmann Ghia like Cliff’s character drives. And even that whole shot where you see Cliff driving by those signs, well that’s pretty much my view looking up at my stepfather in the Karmann Ghia as we drove around Los Angeles. It’s me looking up at him like that, an angle that is very similar to what we had with Brad. So yeah, in the same way that Jackie Brown I think has me trying to capture the South Bay of the 80s. That’s what I was trying to do with this.

A lot of the characters in the film are fictional or perhaps inspired by real people. But the film also features some real characters. And Margot, you play Sharon Tate, who is very much a real person. What is your Sharon like?

MARGOT ROBBIE: I think, definitely what I felt when reading the script was that she was a bit of a hot beat throughout the story. And I wanted to therefore inject her with as much life as possible. And also, to try and show the best parts of myself because by all accounts for anything I’ve ever read about her, people say how wonderful she was and generous. Also, I think at that time it was an incredibly exciting time in her life. She was newly married, and her career is really taking off and Hollywood is an exciting place where there’s so much opportunity and experience to be had. Therefore I wanted her to feel hopeful, I wanted her to feel excited. Yeah, it was really beautiful to be able to have quiet moments to ourselves where she’s just kind of loving life in Hollywood.

 cleanString caption

And there’s that wonderful scene where she essentially goes to see a film that she’s in. Have any of you done that in real life?

TARANTINO: I did that once, at the Bruin, no less.

LEONARDO DiCAPRIO: Wonder where you got it from then!

TARANTINO: I was on a date, and I went to see True Romance and I thought, you know, “I wrote this thing, maybe they’ll let me in for free.” Not because I was stressing the money, but actually I’m in the movie. I’m not stressing the 75 cents, she’s almost just proud to be in the movie, do I get a little consideration?

PITT: That’s funny.

TARANTINO: And so I bring it up to the manager and my girlfriend starts negotiating. And he’s like, “Well how do I know he wrote the film?” “He can show you his driver’s license, his name is right there.” But then Reservoir Dogs had already come out so the a couple of people come up to me and start asking for my autograph. So I’m signing my autograph and the manager at the theater goes, “Well who are those people?” and my girlfriend goes, “Those are his FANS!”

ROBBIE: Did you end up getting to go in?


And Leo, tell us about your character in Once Upon a Time In Hollywood.

DiCAPRIO: It was interesting to play this sort of guy that has reached this expiration date. And the ’60s have come along and as Quentin eloquently puts in the movie, he’s an actor that has spent his career combing his hair and creating a pompadour his whole life. That’s what he knows. And he’s not making this sort of transition into the new era of Hollywood and he’s also feeling sorry for himself. He’s a working actor but he kind of missed out on that television-to-film transition that actors like Steve McQueen did, where they were able to make that jump and have these sort of amazing careers. He’s stuck in this rut.

What’s so interesting is that Quentin puts this all in this sort of two-day time span and gave this amazing back story to all of us. But so much of these characters and what they’re going through emotionally, this transition that Rick Dalton is going through, accepting his sort of fate but also realizing that if he gives a little more and tries a little harder and stops feeling so damn sorry for himself, there are some possibilities out there. What was so great was to be able to have all that knowledge and all that wealth of our backstory in this two-day time span.

And how did you prepare to play an actor full of self-doubt? Was that a reach?

DiCAPRIO: I think that it’s implicitly in all of us. There’s not an actor out there who wouldn’t identify. It’s just a matter of letting the twelve-headed Hydra come out.

I wasn’t picking on you particularly! And Brad, you play a stunt man who is essentially in a different era would be the Batman, really, to Leo’s character. Not the cartoon character, but the assistant, the guy that fixes things.

PITT: The gopher!

Well yes, I didn’t want to say it. Tell us a little bit about your character.

PITT: Yeah, just that! They come from this era when actor and stuntman had a greater partnership and had more say on what was going to be in film, what would take place in a scene. And at this point we’re on the tail end, and I say “we” because I’m on his coattails. I have a job if Rick Dalton has a job, and if Rick Dalton doesn’t have a job I probably don’t. He’s kindly hired me to work odd jobs. I am doing whatever he needs.

You have the best pet-feeding sequence since The Long Goodbye, when he’s getting the cat food. What was that like?

PITT: I can’t take any credit for that. It’s a very, you know, Quentin’s constructed this two days in a life or what becomes two and a half days ultimately, but two days in a life of these characters in different stratas of their careers and life in Hollywood.

 cleanString caption

Margot, how did you get cast in the film? You wrote Quentin a letter?

ROBBIE: I definitely didn’t expect it to work out so well. I just wanted to let him know how much I loved his movies and how it shaped my childhood. And we  met up and had lunch and chatted and he was like, “Do you know who Sharon Tate is?” And I said, “Yeah I do, yeah.” We spoke and I got to read the script and I think it was a similar process, we all go to sit in Quentin’s kitchen nook and read the script.

PITT: I wasn’t even allowed in the kitchen, I got sent to the back porch!

ROBBIE: Oh really? I got food and everything.

Leo, what did you get? She got food, he got tea.

DiCAPRIO: I was out on the porch.

TARANTINO: I left and when I came back, [Margot] was all spread out on the couch, her shoes are off. There’s a Margot imprint on the couch when she leaves.

PITT: And by the way, not to hijack or story…or to hijack your story, he had one script. I went back a couple times. You get there the first time and it’s dog-eared here, a little stained there. By the time I came back a second time there’s like coffee rings, spaghetti sauce, the thing’s all crinkled.

Leo, you have this amazing scene with Luke Perry, who plays a TV actor like your character is, essentially. And sadly we lost him since the film was completed. Can you talk a little bit about working with him?

DiCAPRIO: I was immediately struck by his kindness. And you know talking about being a native of Los Angeles, being around this industry my entire life, and really having it in a lot of ways shape who I am, there was this immediate excitement in seeing Luke Perry on set. I remember being in my teens and he was the manifestation of the new Dean on television and everyone was crazy about him. And I felt this overwhelming feeling of being star struck. Then he and I got to sit down and talk about Los Angeles, the ’90s, his life, where his career had gone, where my career had gone, where his life had gone, where my life…and I was just so, how do I say this, the kindness of his character, I don’t know, it really affected me. When I heard that news it was really heartbreaking.

PITT: Incredibly generous man.

And Brad, I believe there is a bit of this in the trailer, but you have a fight scene at one point with Mike Mo, who plays Bruce Lee. What was that like?

PITT: It was pretty good fun. I love Mike Mo’s story because he was an actor, who things weren’t working out for him so he moved away. To provide for his family he opened up a dojo but when he heard about this…did he contact you?

TARANTINO: No, he didn’t contact me. He contacted Vicky, yeah.

PITT: He contacted casting. Getting the part, he moves away and gets the part. And comes back and does this, he’s really brilliant.

TARANTINO: He tells a great story. So, he’s an actor, he’s done the show Inhumans but basically he runs a dojo out of Wisconsin. And so, he got the part, and he’s going to go back to Wisconsin but he got the part soon enough so he could stay a few days so he could be at the script reading. So we just invite him to the script reading. So, I want you to come read Bruce Lee at the script reading. And he’s already got the part. So, he shows up there, and he doesn’t really know who’s in the movie. So, he shows up there and then Brad walks in the door, and then Leo walks through the door, then Margot walks through the door, and Al Pacino walks through the door, and Burt Reynolds walks through the door, and Luke Perry walks through the door…and he’s like flipping the f out. He’s just like, “Keep it cool, just keep it cool. Don’t let everybody know that you are freaking out to sit at this table.”

PITT: Aww. That’s awesome. That’s a Hollywood story.

I went to the Playboy Mansion I guess a few years before…There’s a dance sequence, although it’s more than a dance sequence, because there is a party at the mansion. And I’m sitting there thinking, “They did a hell of a job recreating the mansion.” Then I realized that it was actually at the mansion.

PITT: A purist! You’re sitting next to a purist, my friend.

Obviously the Hef days are over, but what was it like shooting there?

 cleanString caption

ROBBIE: So coooool!

TARANTINO: It was so much fun. I’ve been to the Playboy Mansion many times in Hef’s day, so…well not many times. But, enough.

An appropriate amount!

TARANTINO: I knew where the grotto was.

PITT: And the Purell. He knew where the Purell was. And didn’t he have a theater room?

TARANTINO: Oh yeah! His theater room is, you know when she comes walking in dancing by the two stairs? The theater room is just back there. I think they all set up couches and had us training on a different spot. It was just fun, iconic, it suggested a Hollywood of a different time. And in ’69, you could go to the Playboy Mansion and Momma Cass could be sitting there next to Sharon Tate sitting there next to Tony Curtis and Audie Murphy. He kind of covered the whole thing. In fact apparently I’ve found that when Hef would do his movie nights, a female friend of mine showed up at a couple, they were really great but they weren’t hip. That was what was neat about them. I asked her what she meant and she said, “It’s like all these cool old actors, you know 79-year-old Robert Kulp.” So it was all these really cool actors from the ’60s who were friends of Hefner’s who still go to the Playboy Mansion to watch movies with Hef. And they’ve all gotten older but it’s all groovy.

Leo, you have a musical moment in the film as well, when your character appears on the real show Hullabaloo singing. What was that like?

DiCAPRIO: Well, thank God I wasn’t hired for my voice for this movie. We had a couple different songs that we tried. One of them was “Green Door” and another was “Don’t Fence Me In.” We ended up using “Green Door,” but, you know, great. It was a lot of fun. And Rick Dalton isn’t sort of hired either for his acting talent for most jobs and most certainly not his singing voice and this is a good display of that.

[To Pitt and DiCaprio] You do in the movie seem to have a very easy-going relationship. Did you know each other particularly well before-hand? Did you just fall into it?

PITT: Certainly over the decades we’ve crossed paths. There’s a a real shorthand with us, we all popped kind of at the same time. Probably all stayed in the same suites. That always freaks me out, by the way. It’s a little weird when you think about it. I mean the same ROOM. The same beds, the same toilets. Probably the same robes. It’s a little weird…I’m gonna get off of it. Just a real shorthand and respect and good laughs on set. And I think we both know having really close friends to get through this thing in one piece, meaning I guess I’m talking about celebrity, and you need really close friends.

DiCAPRIO: You know you go to locations for eight months at a time and the guy who’s your security, they become your best friends. That’s what I loved about this screenplay, this partnership of these guys that are on the outskirts of this industry and trying to sort of pave their way and find their footing still. And survive as working-class actors in a transitional time in Los Angeles and in America, but they rely on one another, they have one another. It may be a professional relationship but it becomes like family.

Related content:

See all the stars at the Once Upon a Time in Hollywood premiere

Quentin Tarantino says ‘everyone’ wanted to play Brad Pitt’s role in Once Upon a Time in Hollywood

Once Upon a Time in Hollywood is a wild, shaggy thrill ride

How to look Younger: Unpacking the hair and makeup of Sutton Foster & co.

The hair and makeup of Younger: Sutton Foster, Hilary Duff, and more |

 cleanString caption

TV LAND; KohGenDo Cosmetics

Estes says this foundation is why Liza looks more than a decade, well, younger: “It was created for HDTV. When the light hits it, it adds a real magic pop to the skin.”

KohGenDo Maifanshi Moisture Foundation, $70 (

 cleanString caption

Diana’s look is all about power, and she “loves red MAC lipstick,” says Estes. As for her hair, “she tucks it in on the left and leaves the right free so she can peer out from behind it,” says Bradley-Sherron.

MAC Cosmetics Satin Lipstick in MAC Red, $18 (

Molly Bernard

 cleanString caption

“Her character is dramatic and there’s not a lot of rules for her makeup,” says Estes, who says Bernard favors cruelty-free makeup from ILIA and Kosas. “She wears bright pinks and purples the other girls don’t wear.”

Kosas 10-Second Eyeshadow in 333, $28 (

Hilary Duff

 cleanString caption

“Kelsey’s running the show, so she’s upped her look to be more sophisticated,” says Estes. That means “skin on point” and “glossier in the lip,” with soft pink and rose gold glosses by Pat McGrath.

Pat McGrath Lust: Gloss in Flesh Fantasy, $28 (

Related content:

Episode Recaps


this link is to an external site that may or may not meet accessibility guidelines.

How DCs Legends of Tomorrow is living its best life as TVs superhero underdog

“That’s DC Comics,” says executive producer Phil Klemmer, pointing across the street at the towering building that houses the publisher’s offices, just a stone’s throw from the Legends of Tomorrow’s writers room at Burbank Studios. “They look down on us, both figuratively and literally.”

This joke — which Klemmer cracked with a chuckle as we stepped outside for the writers’ daily post-lunch walk around the lot mid-June — is classic Legends, irreverent and self-deprecating in equal measure. This show has poked fun at its network’s “dare to defy” slogan; had a character say “hard pass” to last year’s annual Arrowverse crossover; and ended its fourth season with three of its D-list superheroes dressing up as the titular heroes of Arrow, The Flash, and Supergirl because they realized the world they were trying to save wouldn’t listen to them since they weren’t as popular as the Trinity.

In fact, Legends of Tomorrow — which is featured on one of the five Arrowverse covers gracing the latest issue of Entertainment Weekly — has fully embraced the fact that it might not be as traditional as its caped brethren on The CW. “We’re all more comfortable being underdogs,” executive producer Grainne Godfree tells EW. “It’s like the nobility of [The Big Lebowski’s] The Dude. He’s a slacker, but he’s also a hero. We all like those slacker heroes.”

 cleanString caption

The gloriously insane CW super-series is centered on a band of lovable screwups who attempt to defend history from a coterie of threats, including a murderous unicorn, an immortal tyrant, and a dragon demon. The subversive dramedy’s cheeky sense of alienation from the rest of the Arrowverse is at least partially due to the lukewarm critical reception to its relatively conservative and uneven first season, which actually strengthened the cast and writers’ bond. “It’s definitely been us against the world,” Caity Lotz, who plays Sara Lance/White Canary, says with a laugh. “We’re so lucky there is that family element within the cast and writers. They take care of us, which is really nice.”

In the wake of that uneven first season — which followed the titular time travelers as they chased after Vandal Savage (Casper Crump) — the producers took a hard look at the show to figure out what worked and what didn’t. “Season 1 was kind of like the out of town part of a Broadway show and you have a chance to make it better,” says executive producer Greg Berlanti. “[The producers] really embraced the thing that’s different about TV than almost any other visual storytelling form: it changes as it goes.” In season 2, Legends swerved into the wackiness of its premise — a bunch of nobody heroes jumping through time — and that impulse has only grown in the ensuing seasons, leading to the show’s magum weird opus: The season 3 finale battle between the demon Mallus and Beebo, a giant blue Tickle-Me-Elmo-like toy that the Legends formed like Voltron. “When we make those kinds of decisions, there’s this notion in the back of our minds of, ‘People are going to hate this stuff,’” says Klemmer. “You start building the armor and being like, ‘If they don’t like, they don’t get it. They’re not sophisticated enough!’ But then when people do like it, it’s so surprising because, again, we, like the Legends, never expect people to accept us.”

But accept them people have. The reviews have improved as the show has become more idiosyncratic and zany (see: the Puppets of Tomorrow and the Regency-era England-set Bollywood musical number). In December 2018, halfway through season 4, Legends landed on several criticsyear-end-lists— and it’s now frequently hailed as one of TV’s best superhero shows. “We don’t play it safe. The show isn’t a traditional, ‘Let’s figure out how to package this and sell it to the masses.’ I feel like it’s really authentic and original,” says Lotz. Adds Berlanti, “When I watch Legends, it reminds me the most of any of our shows, of reading the Marv Wolfman comics when I was a kid. It’s funny. It’s zany. It’s still emotional. It’s not too earnest in the wrong ways.” This praise, though, has actually created a problem for the writers as they head into the fifth season (airing in 2020).

“If we become popular, are we going to lose our mojo?” wonders Godfree, explaining that the show’s season 5 premiere is a mockumentary that sees the Legends adjusting to their newfound fame after publicly saving the world in the heartwarming season 4 finale. “They’re famous for the first time and some of them are loving it. You have Sara, the stalwart captain who’s the most suspicious of this [and] is not into it.”

“We’re interested in how fame affects people [in season 5],” says Klemmer. “I really like the idea of tempting the Legends, that they’re still susceptible. Even though they sort of get over themselves after [the first episode,] I think you could always be tempted by the promise of getting to be a singular franchise-driving superhero.”

 cleanString caption

The season’s concern with fame also relates to the encores — a.k.a. reincarnated bad guys of history that season 5 bad big Astra (Olivia Swann) released back into the world of the living at the end of last season — the Legends will face.  “It’s like these people who were power hungry and attention-obsessed and, you know, wanted to rule the world. It’s definitely similar to sort of fame culture we have today,” says EP Keto Shimizu, with Godfree adding, “They have that desire for fame and notoriety, as opposed to the Legends who, because this is an ensemble show, understand the simple joy that comes from family.”

Of course, the season’s other main concern is the Zari (Tala Ashe) of it all. In the season 4 finale, Zari disappeared from the Legends and was replaced by her brother Behrad Tarazi (Shayan Sobhian) because defeating Neron erased the dystopian future from whence she came, which means her brother never died and she never got the air totem. Thankfully, that wasn’t the last we’ve seen of Ashe’s heroine, and the show will explore her relationship with Behrad in season 5. “That’s the one energy we’ve never had,” Klemmer says of their sibling dynamic. “That seems like it’s going to be fun.”

As Klemmer and Godfree focus on season 5, Shimizu is currently working on the forthcoming crossover, “Crisis on Infinite Earths,” with the Arrowverse’s other writers. Says Shimizu, “I’m there making sure that, no matter what happens in the massive craziness in the crossover, we have the characters that are participating in [‘Crisis’] land in a very particular place.” Knowing Legends, that place will probably be wonderfully weird.

DC’s Legends of Tomorrow returns in 2020 on The CW.

 cleanString caption

For more on how the Arrowverse saved the TV superhero, pick up the August issue ofEntertainment Weekly on stands July 25-26. You can buy all five covers, or purchase your individual favorites featuring Arrow, The Flash, Supergirl, White Canary, and Batwoman. Don’t forget to subscribe for more exclusive interviews and photos, only in EW.

Related content: 

DC’s Legends of Tomorrow star Caity Lotz reveals Sara gets a superpower in season 5

How Arrow saved the TV superhero — and why it had to end

See exclusive portraits of the Arrowverse stars from EW’s cover shoot

Episode Recaps

How Arrow saved the TV superhero — and why it had to end

Stephen Amell is dreading the eighth and final season of Arrow, though you wouldn’t know it on this hot, sunny July day in Los Angeles. Wearing Green Arrow’s new suit, the CW star seems perfectly at ease as he strikes heroic pose after heroic pose on a dimly lit stage. But once he’s traded heavy verdant leather for a T-shirt, jeans, and baseball cap, his guard drops and the vulnerability starts to creep in as he contemplates Arrow’s last 10 episodes, which was set to begin production in Vancouver a week after the EW photoshoot took place and premieres Oct. 15.

“I’m very emotional and melancholy, but it’s time,” Amell — who is featured on the new cover of Entertainment Weekly — says as he takes a sip from a pint of Guinness. “I’m 38 years old, and I got this job when I was 30. I’d never had a job for more than a year. The fact that I’ve done this for the better part of a decade, and I’m not going to do it anymore, is a little frightening.”

 cleanString caption

Developed by Greg Berlanti, Marc Guggenheim, and Andrew Kreisberg, Arrow debuted in the fall of 2012. The DC Comics series follows billionaire playboy Oliver Queen (Amell), who, after years away, returned to now–Star City with one goal: to save his home-town as the hooded bow-and-arrow vigilante who would become known as Green Arrow (it would take him four seasons to assume the moniker). What began as a solo crusade eventually grew to include former soldier John Diggle (David Ramsey), quirky computer genius Felicity Smoak (Emily Bett Rickards), lawyer-turned-hero Laurel Lance/Black Canary (Katie Cassidy Rodgers), and the rest of Team Arrow. Together they’ve defended their city from a host of threats — dark archers, megalomaniacal magicians, and the occasional metahuman — while Lost-like flashbacks revealed what Oliver endured in the five years he was away, first shipwrecked and then honing his skills around the world to become someone else, something else.

The premiere gave The CW its most-watched series debut since 2009’s The Vampire Diaries. But before they launched Arrow, Berlanti and Guggenheim had to suffer through a failure: 2011’s Green Lantern, starring Ryan Reynolds. The duo co-wrote the script but lost creative control of the film, which flopped. So when Warner Bros. Television president Peter Roth approached them in late 2011 about developing a Green Arrow show, they were wary. After much deliberation, Berlanti and Guggenheim agreed, on the condition that they maintain control. Says Guggenheim, “As long as we succeed or fail on our own work, and not someone else’s work then maybe this is worth a shot.”

Their take on the Emerald Archer — who made his DC Comics debut in 1941 — was noteworthy from the beginning. Taking cues from films like The Dark Knight and The Bourne Identity and series like Homeland, the writers imagined a dark, gritty, and grounded show centered on a traumatized protagonist. “As we were breaking the story, we made very specific commitments to certain tonal things, such as ‘At the end of act 1, he has his hands around his mother’s throat.’ And, ‘At the end of act 2, he kills a man in cold blood to protect his secret,’ ” says Guggenheim.

A hero committing murder? That was practically unheard of then. Having Oliver suit up in a veritable superhero costume by the pilot’s climax was radical too. Sure, the Marvel Cinematic Universe was deep into Phase One when the producers were developing Arrow, but TV was traditionally more apprehensive about comic books. Smallville famously had a “no tights, no flights” rule and only introduced superhero costumes in the last years of its 10-season run, and there weren’t any masked avengers running around NBC’s Heroes or ABC’s No Ordinary Family, the latter produced by Berlanti (Let’s not even mention NBC’s The Cape, which was essentially dead on arrival and never did get its six seasons and a movie). But Arrow not only fully committed to the idea of someone dressing up like Robin Hood to fight crime with a bow and arrow, it introduced a second costumed rogue, the Huntress (Jessica De Gouw), in episode 7.

“It’s just comic book to the extreme and the fans seem to really love it,” says Batwoman showrunner Caroline Dries, a former writer on Smallville. “They still maintain it very grounded, but it’s very different with everyone in costumes. The appetite for superheroes has changed in my mind in terms of like they just want the literal superhero [now].”

Not that the team wasn’t meticulous about creating Green Arrow’s cowl. “We had to have so many conversations to get it approved, but that’s why we got [Oscar winner] Colleen Atwood [Memoirs of a Geisha] at the time to [design] the suit,” says Berlanti. “We were determined to show we could do on TV what they were doing in the movies every six months.”

“It’s really easy to make a guy with a bow and arrow look silly. We sweated every detail,” says Guggenheim, who also recalls how much effort it took to perfect Oliver’s signature growl. “I actually flew up to Vancouver. On a rooftop during reshoots on [episode 4], Stephen and I went through a variety of different versions of, basically, ‘You have failed this city,’ with different amounts of how much growl he’s putting into his performance. [We] recorded all that, [I went] back to Los Angeles, and then sat with the post guys playing around with all the different amounts of modulation.”

That process took eons compared to the unbelievably easy time the team had casting Arrow’s title role. In fact, Amell was the first person to audition for the role. “It was Stephen’s intensity. He just made you believe he was that character,” says Guggenheim, recalling Amell’s audition. “We had crafted Oliver to be this mystery box character, and Stephen somehow managed to find this balance between being totally accessible in a way you would need a TV star to be, but he’s still an enigma.” After his first reading, Amell remembers being sent outside for a short time before being brought back into the room to read for a larger group: “I called [my manager], and I go, ‘I know this is not how it’s supposed to work, but I just got that job.’”

 cleanString caption

In the first season, the show’s chief concerns were maintaining both the “grounded and real” tone and the high quality of the stunts, and investing the audience in Oliver’s crusade. Beyond that, though, there wasn’t much of an over-arching plan, which allowed the show to naturally evolve — from introducing more DC characters, such as Deathstroke (Manu Bennett) and Roy Harper (Colton Haynes), sooner than they initially intended (the shot of Deathstroke’s mask in the pilot was meant as a harmless Easter egg), to promoting Emily Bett Rickards’ Felicity from a one-off character in the show’s third episode to a series regular in season 2 and eventually Oliver’s wife. Even the whole idea of a Team Arrow — which, over time, added Oliver’s sister Thea (Willa Holland), Rene Ramirez/Wild Dog (Rick Gonzalez) and Dinah Drake/Black Canary (Juliana Harkavy) — was the result of the writers allowing the best ideas to guide the story. “Greg used to say all the time, ‘You have a hit TV show until you don’t, so don’t save s—,’ ” says Amell.

Also not planned: Arrow spawning an entire shared universe. “We went on record a lot of times during the premiere of the pilot saying, ‘No superpowers, no time travel.’ But midway through season 1, Greg started to harbor a notion of doing the Flash,” says Guggenheim. “I’m a very big believer that it’s great to have a plan, but I think when it comes to creating a universe, the pitfall is that people try to run before they can walk. The key is, you build it show by show.” And so they did. First, they introduced The Flash star Grant Gustin’s Barry Allen in the two-part midseason finale of Arrow’s second season. From there, Supergirl took flight in 2015, then DC’s Legends of Tomorrow in 2016, and Batwoman is due this fall. “It’s like the hacking of the machete in the woods and then you look back and you’re like, ‘Oh, there’s a path,” says executive producer and Berlanti Productions president Sarah Schechter. But even though Arrow is the universe’s namesake, Amell doesn’t concern himself with the sibling series outside of the now-annual crossovers. “I never think about any of the other shows,” he says. “I want all of them to do great, but they’re not my responsibility. My responsibility is Arrow, and to make sure everyone from the cast to the crew are good.” His sentiments are seconded by Flash’s Gustin: “I don’t understand how he does it — his schedule that he maintains with working out, the conventions he goes to, the passion he has for it, and the love he shows towards fans. He’s always prepared. He cares more about that show being high quality than anybody else on the set.”

That said, the universe’s expansion precipitated what is widely considered to be Arrow’s best season, the fifth one. After focusing on magic in season 4, the show returned to its street-crime roots as part of “a concerted effort to play not just to our strengths but what made the shows unique,” Guggenheim says of balancing their four super-series in 2016. “Because Arrow was the longest-running Arrowverse show, we were able to do something that none of the other shows could do, which is have a villain who was basically born out of the events of season 1,” he explains of introducing Adrian Chase/Prometheus (Josh Segarra), whose criminal father was killed by Oliver. “That gave the season a resonance.”

It was midway through season 6 when Amell realized he was ready to hang up Oliver Queen’s hood. “It was just time to move on,” the actor says of pitching that Oliver leave the series at the end of season 7. “My daughter is turning six in October, and she goes to school in L.A., and my wife and I want to raise her [there].” Berlanti persuaded him to return for one final season, which the producers collectively decided would be the end. “We all felt in our gut it was the right time,” says Berlanti. Adds Schechter, “It’s such a privilege to be able to say when something’s ending as opposed to having something just ripped away.”

But there’s one integral cast member who won’t be around to see Arrow through its final season. This spring, fans were devastated to learn Rickards had filmed her final episode—bringing an end to Olicity. “They’re such opposites. I think that’s what draws everyone in a little bit,” showrunner Beth Schwartz says of Oliver and Felicity’s relationship. “You don’t see the [love story of] super intelligent woman and the sort of hunky, athletic man very often. She’s obviously a gorgeous woman but what he really loves is her brain.” For his part, Amell believes the success of both Felicity and Olicity lies completely with Rickards’ performance. “She’s supremely talented and awesome and carved out a space that no one anticipated. I don’t know that show works if we don’t randomly find her,” says Amell, adding that continuing the series without Team Arrow’s heart is “not great. Arrow, as you know it, has effectively ended. It’s a different show in season 8.” And he’s not exaggerating.

The final season finds Oliver working for the all-seeing extra-terrestrial the Monitor (LaMonica Garrett) and trying to save the entire multiverse from a cataclysmic event. “[We’re] taking the show on the road, really getting away from Star City. Oliver is going to be traveling the world, and we’re going to go to a lot of different places,” says Guggenheim. “Every time I see Oliver and the Monitor, it’s like, ‘Okay, we are very far from where we started.’ But again, that means the show has grown and evolved.” Adds Schwartz, “This is sort of his final test because it’s greater than Star City.” Along the way, he will head down memory lane, with actor Colin Donnell, who played Oliver’s best friend Tommy Merlyn in season 1, and Segarra’s Adrian Chase making appearances. “Episode 1 is an ode to season 1, and episode 2 is an ode to season 3,” teases Amell. “We’re playing our greatest hits.”

But season 8 is not just about building toward a satisfying series finale. “Everything relates to what’s going to happen in our crossover episode, which we’ve never done before,” says Schwartz. Spanning five hours and airing this winter, “Crisis on Infinite Earths” will be the biggest crossover yet and may see Oliver perish trying to save the multiverse from destruction, if the Monitor’s prophecy is to be believed. “Oliver [is told] he’s going to die, so each episode in the run-up to ‘Crisis’ has Oliver dealing with the various stages of grief that come with that discovery,” says Guggenheim. “So the theme really is coming to terms, acceptance.”

If there’s one person who has made his peace with Oliver’s fate, it’s Amell. “Because he’s a superhero with no superpowers, I always felt he should die — but he may also not die,” says Amell, who actually found out what the show’s final scene would be at EW’s cover shoot. “I cried as [Marc Guggenheim] was telling me. There are a lot of hurdles to get over to make that final scene.” Get this man some more Guinness!

Arrow premieres Tuesday, Oct. 15 at 9 p.m. on The CW.

For more on how the Arrowverse saved the TV superhero, pick up the August issue of Entertainment Weekly on stands July 25-26. You can buy all five covers, or purchase your individual favorites featuring Arrow, The Flash, Supergirl, White Canary, and Batwoman. Don’t forget to subscribe for more exclusive interviews and photos, only in EW.

Related content: 

See exclusive portraits of the Arrowverse stars from EW’s cover shoot

Arrow promotes Katherine McNamara to series regular for season 8

Arrowverse’s ‘Crisis on Infinite Earths’ crossover will include Batwoman, Legends of Tomorrow

CW boss on if Emily Bett Rickards will return for final Arrow season

Billionaire Oliver Queen — under the vigilante persona of Arrow — tries to right the wrongs of his family and fight the ills of society.

Episode Recaps

How Tom Kings Batman run has built up to City of Bane

Writer Tom King’s run on DC’s flagship Batman comic was initially one of the main highlights from the publisher’s DC Rebirth initiative when it launched back in 2016. Three years later, it has become one of the longest-lasting of the initial Rebirth creative teams, and one of the most celebrated — but it all comes to a head this week with the beginning of the “City of Bane” arc.  

As the title suggests, this week’s Batman #75 finds Gotham City overrun by Bane. King’s run has gone a long way towards catapulting Bane into the top-tier of Batman’s rogues gallery (in case Tom Hardy’s Dark Knight Rises portrayal wasn’t enough). Though he first appeared early in the run, Bane was only getting started. 

EW spoke with King recently in a long-running conversation about his run and what it’s been building towards. Some of it was about the epic Batman-Catwoman reunion that will take place during “City of Bane” (after the characters’ failed wedding back in issue #50), but we also discussed how the new story builds on seeds that King has been planting for years. 

Gotham Girl

 cleanString caption

 cleanString caption

The very first arc of King’s Batman was called “I Am Gotham,” and found the Dark Knight confronting a very unusual situation for him: The arrival of two superheroes with actual superpowers in Gotham City. The brother and sister duo called themselves Gotham and Gotham Girl. Though at first, they seemed like a welcome presence in Batman’s life, the dark truth was soon revealed. Their magnificent powers were slowly killing them and driving them insane. Gotham did not survive that first story, while Batman went to great lengths over subsequent issues to save Gotham Girl’s life. 

Flash forward to the present, where Gotham Girl is allied with Bane now. Not only that – she’s one of the main reasons he’s able to control Gotham City at all.  

“What’s awesome about Batman is I’ve been planting these seeds forever and now I’m just watching them grow,” King tells EW. “So going all the way back to issue 5, which is way far back, we showed that Gotham Girl has the power to take down the entire Justice League in about 30 seconds. So, when we talk about a city controlled by Bane, you might ask, why doesn’t Superman just come down and end it? Why doesn’t the Justice League take it over? Because they’ve got an atom bomb. Bane’s not working with someone who can shove a staff in your face, he’s working with someone who can punch Green Lantern into the next galaxy. But of course, the catch to that is, every time she uses her power she dies a little. By using her that way, he’s killing her.”

I Am Suicide

 cleanString caption

 cleanString caption

“I Am Gotham” was followed by an arc titled “I Am Suicide,” in which Batman went toe-to-toe with the Suicide Squad in order to secure Psycho Pirate’s therapeutic powers for the benefit of Gotham Girl. That wasn’t the only meaning of the title, however. As Batman fought his way through Bane’s South American stronghold – since the villain had been using Psycho Pirate for his own ends, to cure himself of addiction to the drug Venom – he revealed via internal narration that he had once attempted suicide.  

This was a shocking revelation for some readers, but King thinks it’s all part of who Batman is. 

“I don’t think I added to the myth; I think it sort of discovered stuff that was already in the myth, if that makes sense,” he says. “The idea is that when Batman got on his knees and made that vow, in some ways he was killing his old self. He was saying, ‘I have no more use for Bruce Wayne. I’m now this other thing. I’m the man who wars on criminals.’ I think that was always there, I just made it a little more, maybe, explicit.”

King adds, “There’s a reason I’m not Batman, and you’re not Batman, and even the Delta Force guys aren’t Batman. They care about something other than being Batman, but Batman only cares about that. You and I don’t go out every night and punch people in the face because we care about things like our family and not getting punched, but Batman only cares about that.”

Only future issues will be able to tell whether that singular determination is enough to overcome Bane. 

Thomas Wayne

 cleanString caption

 cleanString caption

A few years before DC Rebirth, the publisher reinvented its entire line. Previous continuity was erased, and every comic series started off from a new issue #1. This initiative was called “the New 52,” and it was accomplished through an event series titled Flashpoint in which the Flash went back in time to try to save his mother’s life; in doing so, he created massive changes to the time-space continuum. Before things settled down into the New 52 status quo, readers glimpsed an alternate what-if universe with radically changed DC heroes. The most interesting element of that Flashpoint world was that the Batman mantle was worn not by Bruce Wayne, but his father Thomas. In that world, it was Bruce who was killed that fateful night in Crime Alley, while his father took a vow of revenge and declared a war on crime. 

In May 2017, King’s Batman briefly crossed over with The Flash for a story called “The Button,” in which Bruce finally came face-to-face with the version of his father from this alternate dimension. Thomas, who in this incarnation has lived his own lifetime as Batman, declared that he did not want his son doing the same. 

“I’m a writer — I’m fairly successful at it — but if my son was to come to me and say, ‘Dad, I want to be a writer. In order to do that, I’m going to throw away my entire life. I’m gonna be totally obsessed with it. I’m gonna risk my well-being every single day. I’m just gonna be in love with being a writer and only care about writing for the rest of my life,’ I’d be like, ‘no, no, no don’t do that. That’s an absolutely horrible idea. You need balance in your life,’” King says. “Then it becomes an idea of addiction. The way his father sees it is, ‘My son is addicted to something. He made this suicidal choice and now he can’t quit.’ So Thomas Wayne, and this becomes explicit in issue 74, is like, ‘I can’t break your addiction by being the nice dad, I’m going to break your addiction by bringing you to your lowest point.’”

Thomas wasn’t kidding. He’s willing to go to any lengths to save his son from the torment of being Batman…even if it means teaming up with Bane to take over Gotham. Thomas becomes Bane’s top lieutenant – “the Darth Vader to his Emperor,” in King’s words.

Kite Man

 cleanString caption

 cleanString caption

One of the most fascinating recurring characters in King’s Batman has been the villain known as Kite Man. Despite Batman’s long and storied list of villains, Kite Man is probably not a name you’ve heard much before. Though he was originally created by Batman co-creator Bill Finger himself back in 1960, Kite Man has gotten new life thanks to King, who seized on the villain’s name being Charles Brown and turned him into a tragic everyman figure, a villain who just can’t get anything to work for him. Kite Man played an integral role in King’s epic “War of Jokes and Riddles” arc, and will also feature prominently in “City of Bane.”

“He does have an outsize role,” King says. “I was basically saying to [‘City of Bane’ artist] Tony S. Daniel, who can draw beautiful stuff, ‘you could draw any villain in the world here… but we’re gonna focus on Kite Man.’ He’s got a big role because the city is controlled by villains, and he’s a villain. When it comes to what working for Bane is like, and what fears go with that, our man on the ground is Kite Man. As usual, Lucy always takes the football and he always falls on his back. Poor fellow.”


 cleanString caption

 cleanString caption

 cleanString caption

It all comes back to Catwoman. The romance between “Bat” and “Cat” has been a major part of King’s Batman so far, and will strongly influence his endgame. One of the standout issues from the run was issue #49, the one just before the attempted wedding, in which Catwoman found herself in an hours-long stand-off with the Joker. As they both laid on the ground clutching their bleeding wounds, the two reminisced about the old days in between threatening to kill each other. It was a beautiful mess of divergent tones that also made perfect sense.

“Comic books are fundamentally absurd,” King says. “They make no sense if you read them, especially if you read them under the presumption that all of this happened to one person. It’s completely nonsensical. The thing that mitigates that is that life itself is fairly nonsensical. So the absurdity of comics can become a metaphor for the absurdities we go through every single day — which is good because a lot of movies give you these straight-ahead plots where there’s a first act, a second act, and a third act, and it all resolves. That’s not life. Life is like a comic book. Life is ongoing and, at least to you, never-ending. So, that’s what I do. I take that absurdity seriously because when we look around everyday, we take absurdity seriously.” 

King continues, “That’s just like one day in your job, where you’re talking about some stupid TV show. Then you go home that night you have to talk about your father dying of cancer, and then later that day you have to talk about the groceries. Your brain has to process it all. And then you turn on the news and everything’s falling apart. All of these things have to exist in you at once and that’s what comics can be.”

In that issue, the Joker strongly implied that if Catwoman married Batman and made him happy, then he wouldn’t be Batman anymore. And in that case, who would be around to stop the Joker from killing everyone? That’s a question Catwoman has struggled with. But another important reminder from that encounter is that she knows Batman’s villains almost as well as he does. Together, the two of them might be Gotham City’s only shot at salvation. 

“For the past 25 issues, I’ve been torturing both myself and the audience, sort of tearing Batman apart get him to his lowest point,” King says. “I’m super proud of those issues, but I knew looking at my outline this was going to be tough to write and tough for the audience. It’s gonna be just tough for everyone. And we’re finally turning that corner. We’re at that low point — Wolverine at the bottom of Hellfire Club being like, ‘Now it’s my turn.’ Or John Wick seeing his puppy die and being like, ‘Alright it’s on.’ We’re there. To me, it feels like it’s a good place to take a breath before we start our last leg. You’re running that 400 dash and your best runner just got the baton.”

Batman #75 is available now. 

Related content:

How The Rise of Kyoshi YA novel finds new things to love about Avatar: The Last Airbender

The Avatar lives again! Just as the titular character of Avatar: The Last Airbender is constantly reincarnated from one elemental nation to the next, so too has the Avatar universe grown — from its beginnings as an animated TV show, to a live-action movie, then to tie-in graphic novels, and now to prose novels.

This week sees the release of The Rise of Kyoshi, the Avatar universe’s very first canonical prose novel. Written by F.C. Yee (The Epic Crush of Genie Lo) with advisement from Michael Dante DiMartino (who originally co-created Avatar: The Last Airbender with Bryan Konietzko), The Rise of Kyoshi is a stunning revitalization of Avatar storytelling that uses the YA novel format to explore new depths within its world, exploring the internal mental state of element-bending and developing a compelling same-sex romance. 

Front and Center, Finally

True to its title, the new novel focuses on Avatar Kyoshi. Born into the Earth Kingdom (one of the four nations of the Avatar world, each matched to one of the classic elements), Kyoshi held the Avatar mantle two generations before Aang, the famed “last airbender.” Longtime Avatar fans may have first heard of Kyoshi in one of the earliest episodes of The Last Airbender, “The Warriors of Kyoshi,” in which Aang and his friends first encountered the Kyoshi Warriors of Kyoshi Island. The all-female group were capable fighters who protected their ancestral homeland while dressed in the kabuki makeup of their namesake idol and wielding her trademark weapons: Fans.

Kyoshi’s unique look made her a visual stand-out whenever Aang was greeted by visions of his past lives. But The Rise of Kyoshi looks at the woman behind the makeup, showing how she went from a dirt-poor nobody to an inspiring legend. Thanks to the prose format, Yee’s novel has the space to expand on mythology that was only hinted at in previous works. Readers don’t get to see Kyoshi bend the elements with martial arts the way Aang did on screen, but they do get to live inside her head and see the Avatar world from a whole new angle. 

As The Last Airbender unfolded, it occasionally granted additional pieces of information about Kyoshi. Fans learned she was renowned as one of the most powerful Avatars ever, who lived to 230 years of age. Whenever she manifested herself to speak through Aang (as all past Avatars can do), she displayed a strong sense of justice. Unlike the peace-loving Aang, Kyoshi possessed an iron will to see justice done at all costs. This attitude clearly produced both good and bad results. Kyoshi’s separation of Kyoshi Island from the Earth Kingdom mainland successfully protected the community for posterity and ended the tyrannical ambitions of Chin the Conqueror, but made her a reviled figure in Chin’s hometown. Kyoshi also founded the elite Earth Kingdom secret police known as the Dai Li, who protected the Earth King’s life at the cost of slowly funneling the monarch’s political power into their own shadowy order.   

The character we meet in The Rise of Kyoshi is a long way from all that, though. 

“What was appealing to me was how with limited screen time, she was such an effective foil to Aang in the original series. They don’t spend that much time together, but it’s so interesting to watch them play off each other with their different approaches to problem-solving,” Yee tells EW. “That got me into thinking about what could be filled in. What kind of experiences would she have had to go through in order to arrive at the woman we see as an adult, who briefly appears and advises Aang, and owns up to slaying a conqueror, and doesn’t take any BS from anyone? She must have seen some pretty intense stuff to give her that edge.” 

Granted, every Avatar needs years of training to master the four elements and grow into their destiny as the savior of the world, but Kyoshi isn’t even recognized as the Avatar at the beginning of the novel. The earthbending sage Jianzhu and the airbending master Kelsang, friends of the late Avatar Kuruk who have been charged with finding and protecting his successor, have instead misidentified the Avatar, lifting up a man named Yun even though Kyoshi is right under their noses. 

This fascinating twist marks a first for the franchise, since both Aang and his successor Korra were identified as the Avatar at an early age and grew up knowing they were meant for greatness. Kyoshi, by contrast, begins as a mere serving girl in the household of the exalted “Avatar Yun.” An orphan since childhood, Kyoshi is used to being reviled by ordinary townspeople. The combination of her potentially earth-shattering powers and her xenophobic reception among average people may remind some readers of N.K. Jemisin’s Broken Earth trilogy. Though when we first meet Kyoshi, her self-esteem is so low she can barely earthbend at all.

“Since the earliest days of Avatar, we’ve always been pitched ideas of a fake Avatar. It seems like a natural thing for writers to glom onto,” DiMartino tells EW. “We never really resonated with that idea, there was never an angle we could figure out that made sense. But the way F.C. did it, it makes sense in this volatile period between Avatars. He came up with a plausible reason they could’ve been misidentified. It’s a great start for Kyoshi specifically: The person who becomes one of the most powerful and legendary Avatars ever starting out where people don’t believe she is and she has to go rogue to learn how to become the Avatar.”

He continues: “It’s a cool angle on the classic Avatar journey of mastering the four elements and having to find your masters and stuff, when she’s treated as an outcast in a way.” 

The Korra Connection

The Rise of Kyoshi also fleshes out a key part of Kyoshi’s character that fans only learned of very recently. The Legend of Korra, the sequel series to Avatar: The Last Airbender that focused on Aang’s headstrong Water Tribe-born successor Avatar Korra, ended with Korra embracing her romantic feelings for her friend Asami. The final minutes of the show found its two female leads taking each other hand-in-hand before walking off into the sunset

The Legend of Korra: Turf Wars trilogy of sequel graphic novels, written by DiMartino and illustrated by artist Irene Koh for Dark Horse Comics, further explored this relationship, as Korra and Asami struggled with coming out to friends and family. This is where Aang’s waterbending daughter Kya came in. Kya approached Korra and Asami during Turf Wars, explained that she also loved women, and gave the two young lovebirds a crash course in the state of LGBTQ affairs within the Avatar world. One of the most interesting tidbits was the revelation of Kyoshi’s bisexuality. Just as The Rise of Kyoshi explains how the Earth Kingdom Avatar learned to fight with fans while wearing kabuki makeup, it also explores her first experience of falling in love with another woman. 

“In the back of our minds we always thought Kyoshi was probably bisexual,” DiMartino says. “For a YA novel, it just seems quite appropriate to have her explore her feelings toward men and women. In the Korra comic, it’s just a line; there wasn’t time to really get into it, so F.C. took that idea and came up with an awesome character Rangi and it’s great. It’s really the heart of the story, which I really like.” 

For a story that’s primarily about martial arts and elemental battles, Avatar has always had a knack for crafting compelling romances. But the blossoming relationship between Kyoshi and her firebending friend Rangi, who start out as co-workers in Yun’s mansion before being drawn together in a daring escape and learning to survive together on the run, also highlights the unique strengths of Yee’s novel. The Avatar shows and graphic novels can visualize the spectacle of bending, but The Rise of Kyoshi gets us into the characters’ heads to see how these elemental powers fuel personalities and relationships. 

At one point, as Kyoshi and Rangi are fleeing from attackers, Yee writes, “[Rangi] ran as nimbly as they did on the roof tiles, and when there was a leap too great to make naturally, she stepped on jets of fire that blasted out of her feet, bounding in propulsive arcs across the sky. The sight made Kyoshi’s breath come to a standstill at the very time she needed it flowing. Rangi was so beautiful, illuminated by moon and fire, that it hurt. She was strength and skill and determination wrapped around an unshakable heart.”  

All About the Words

Until now, Avatar has primarily been a visual story. Both the animated shows and the tie-in comics have used their formats to broadcast the show’s visceral combination of martial arts techniques with elemental powers. But in scenes like this, Yee finds a way to make the components of Avatar storytelling come alive on the page. Other characters, like Jianzhu, use interesting bending techniques that focus on small projectiles or minor manipulations that maybe wouldn’t pop on screen but come alive in the reader’s imagination. 

“I knew it was going to be a challenge capturing the motion and kinetic energy of the series in word form,” Yee says. “If you were going to describe, word for word, everything that happens in a fight scene as complex as the ‘Day of Black Sun’ episode where everyone’s jumping around pillars created by the Dai Li, or the gang’s intrusion on the Earth King’s palace…I felt for me it would be impossible. So I actually drew on a concept from back when I practiced capoeira. For capoeira, when you see two people get into the circle and start moving and it seems like a very fluid thing, the mindset my teachers told me is you’re supposed to be having a dialogue. Rather than doing lots and lots of motions, you’re posing a question to the other person. Then they’re answering and posing one of their own, and you’re interacting that way. That call and response, set up and subversion, was probably better suited for the text form and my own capabilities, so I described fight scenes in that manner.”

The good news is, there’s more where this came from. Kyoshi’s aforementioned 230-year lifespan means there’s lots of room left for additional stories, and Yee is already brainstorming the follow-up novel. He teases, “She is definitely going to be challenged on an intensely personal level, which you might guess from the end of book 1, as well as on the political level, as she goes from the lowest rungs of society and most outcast to the highest levels of the world stage.”

What’s Next

That’s not even all that the future holds for the Avatar universe. DiMartino is currently writing a new trilogy of Legend of Korra graphic novels, this one titled Ruins of the Empire and illustrated by artist Michelle Wong, that explores the fate of the villainous Kuvira; part one is available now. A new trilogy of Avatar: The Last Airbender comics is also currently underway, written by Faith Erin Hicks (The Nameless City) and illustrated by Peter Wartman with consultation from DiMartino. 

Most interestingly of all, DiMartino and Konietzko are hard at work developing a live-action series version of Avatar: The Last Airbender for Netflix. Not much is known about the project, and it’s still early enough that DiMartino couldn’t speak much about it. But with that on the horizon and The Rise of Kyoshi in bookstores this week, it’s clear that Avatar has become one of the richest and most rewarding fictional universes of 21st-century pop culture.

“It’s pretty crazy,” DiMartino says. “It’s just wild that we created it in 2002, and we’re still working on it. It never went away, even when we weren’t working on the show, because I was working on the book or comics. It’s always been part of my life. But this does feel new. The people who grew up with the show are now older and actually working on the shows, comics, and books, and there’s still the next generation discovering it. That was one of our goals originally: To tell a timeless story that could last generations.”

Related content: 

Avatar: The Last Airbender

Complete Coverage
  • Avatar: The Last Airbender

Why Colson Whitehead continues to plunge into American historys dark heart

Colson Whitehead is sitting in a booth at City Diner, around the corner from his Upper West Side apartment and a few dozen blocks from where he grew up as a kid. In between sips of Coke, he’s recalling his process writing Sag Harbor, his semiautobiographical 2009 novel. A dreamy coming-of-age saga rooted in Whitehead’s adolescent memories, Sag Harbor pulses to the beat of ’80s hip-hop; it’s sprinkled with nods to his childhood faves, Star Wars and The Cosby Show. “My earlier books were more detached, a little more clinical,” he says. “This was a real breakthrough for me, in terms of letting it all hang out.”

So, was preparing for the book, his fifth, more difficult than others? He considers the question, then laughs, softly — a tart contrast to the weighty literary persona his work fosters. “Googling Run-DMC is different from reading the autopsy report of people exhumed from the Dozier School,” he deadpans. He laughs again, knowingly this time.

And there’s the reminder that Whitehead, 49, always takes on new challenges — and that, in his consistent focus on the racial tensions of American life, it’s always personal. The abusive Arthur G. Dozier School for Boys, which closed in 2011 (bodies of dead students have been found buried under its grounds), provides the basis for The Nickel Boys, Whitehead’s new novel set in Jim Crow-era Florida and centered on two black boys. A brutal meditation on fate and choice, it marks a slimmer, grimmer return to the bildungsroman structure that Whitehead first mined a decade ago in Sag Harbor, and has yielded a harsher form of emotional catharsis. “I was really depressed those last six weeks I was writing it,” he admits. “I decided on a course for the boys’ story; actually implementing it, as the book was winding down, took a lot out of me.”

Clad in a summery plaid button-up on a late May afternoon, Whitehead exudes a bright sense of humor even as the conversation turns thorny. He recently crossed the 20-year mark as a published author. “I think I’m more in control,” he says of his current work. Reflecting on the beginning of his career, Whitehead argues he pushed “a postmodern exuberance” in his first few novels, posing “What if?” questions and answering them through ironic narrators and an abundance of granular detail. His witty debut, The Intuitionist, came out of, “What if an elevator inspector had to solve a criminal case?” (He answers this surprisingly head-on.) His third novel, Apex Hides the Hurt, traces a branding consultant’s duty to name a small fictional town.

These tales critically examine the American narrative, but they’re more playful, less linked to concrete events. In The Intuitionist, for instance, talk of integration and racism abound, but the unspecified nature of the time-period allows Whitehead to run wild. He still grins just thinking about it. “It’s a world where elevator inspectors are really, really, really important, and that makes me laugh,” Whitehead says. “It’s absurd! It lends an otherworldly quality to the story.”

Now, Whitehead is sitting in the shadow of a global literary phenomenon. The Underground Railroad, published in 2016, won him a National Book Award and the Pulitzer Prize, was selected for Oprah’s Book Club, and sold more than one million copies — shooting him into the pantheon of American authors. (Moonlight’s Barry Jenkins is set to direct the TV adaptation for Amazon.) The book was circling in Whitehead’s brain for 10 years or so before getting published — the author says it too resulted out of that “What if?” impulse, a gonzo response to, “What if the Underground Railroad was real?” — and, accordingly, it nicely delineates his maturation. “I couldn’t have [written it] 20 years ago,” Whitehead says. “Being older, being a parent, and trying to be a less crappy individual improves my work.” He’s resistant to being asked about the book’s social importance: “People are like, ‘Why is it important to learn about slavery?’ It just is!” Another goofy chuckle.

Sylvain Gaboury/Patrick McMullan via Getty Images

Those familiar with Whitehead’s eclectic bibliography — gory zombie thrillers (Zone One), cutting satires of capitalism (Apex), epic alternate histories (John Henry Days) — might have expected a lighter, or at least weirder, novel to follow the genre- and time-bending Railroad, which follows a runaway slave. Yet The Nickel Boys further showcases the author’s visceral historical imagination. The novel is propulsive, its two heroes Elwood and Turner teetering between idealism and cynicism as the plot builds to a devastating climax. Says his editor, Bill Thomas: “A lot of what he’s done in these last two books — Underground Railroad and certainly The Nickel Boys — is reclaim [American history], and make it clear how present it still is.”

Whitehead adds: “Whether you’re a young black man in Florida in 1962, or a young black man in 1986 in New York City, like I was, you can be caught up in the snare of law enforcement at any time. In a split second, your life can change.”

Whitehead was working on a crime novel — still is, in fact — when he learned about Dozier in 2014. “I did feel this compulsion,” he says. “There have not been a lot of novels about teenagers growing up under Jim Crow. There are stories that have not been told…that need to be told.” For research, he dug through university and newspaper archives in Florida, but found a Dozier survivors’ website most useful. “Getting the slang of the characters makes it vivid for me,” he says. “There’s a worldview in slang — like calling the White House ‘The Ice Cream Factory.’ There’s an attitude towards the world. It’s rueful, kind of comic. It helped me understand them.”

Whitehead has now been novelizing this country’s past for 20 years. His theories on his writing’s evolution certainly bear out: He’s more in control, concise, empathetic to his characters. Deep in thought, the author trails off, pondering his creative growth and what draws him to certain stories. His narrators are less existential; his approach has turned tighter, sadder, sharper. And he feels it. As to why he keeps returning to American history’s dark heart? Whitehead lets out one last loud, morbid laugh. “There’s a lot of good material.”

Related content:

20 new books to read in July
Review of Colson Whitehead’s Zone One
The Underground Railroad selected for Oprah’s Book Club

Killer clowns are no joke: Inside the battle between Pennywise and the Losers in It Chapter Two

A couple of years ago, actress Jessica Chastain visited the Warner Bros. lot in Burbank to watch an early cut of a new ’80s-set horror movie by director Andy Muschietti and his producer sister, Barbara. The Zero Dark Thirty actress is friends with the pair, having starred in their 2013 hit fright film Mama, so she was a bit apprehensive viewing the Muschiettis’ latest project with the two of them sitting in the room with her. Barbara gave Chastain a glass of red wine to sip, much of which never made it to her stomach. “In the first five minutes I jumped, and the wine went everywhere,” says the actress. “Right after the movie’s end, Andy goes, ‘You want to do it?’ I go, ‘Yes, I want to do it! Of course I want to do it!’”

The “it” in question, naturally, is It: Chapter Two (out Sept. 6), the sequel to the film Chastain was watching that day. Adapted from Stephen King’s classic novel, 2017’s It tracked a group of misfit kids — who dubbed themselves the Losers’ Club — battling a child-slaying supernatural entity who reveals himself to his prey as a clown called Pennywise (Bill Skarsgård). Despite initial doubts from horror fans that Skarsgård could match Tim Curry’s iconic performance as the fanged entertainer in the much-loved 1990 It miniseries, the Swedish actor and the Losers’ Club turned out to be winners, with the $35 million-budget film praised by critics and going on to gross $700 million at the global box office.

Brooke Palmer/Shutterstock/Warner Bros.

That success is reflected in the production of the sequel. “In general, I feel more comfortable. I have more toys,” says director Muschietti. “On the first one, I was struggling to get a Technocrane [a massive telescopic crane for a camera] on certain days. But now the Technocrane is always there!” His goal: to make an even more overwhelming experience this time around. “I think that everything that people love from the first one, like the humor and the emotions and the horror, will all be there,” says Muschietti, “and cranked up, in some cases.”

It Chapter Two is set 27 years after the events of its predecessor, as Pennywise returns to the streets — and sewer drains — of the fictional New England town of Derry to slay more children…unless the Losers’ Club can stop him. The young cast of the first IT was, unsurprisingly, in large part made up of unknowns, with Stranger Things star Finn Wolfhard, who played the wiseacre Richie, the best known of the bunch. Chapter Two, in contrast, boasts several high-profile actors, including Chastain, who plays Beverly, the lone woman in the Losers’ Club; Bill Hader as Richie; Sinister franchise actor James Ransone as the grown-up version of the supposedly sickly Eddie; and James Mc­Avoy as Bill, who lost his younger brother, Georgie, to Pennywise in the first film.

Bill has gone on to become a Hollywood screenwriter. “He’s in L.A. shooting a movie,” says the X-Men star, describing his character as a “Stephen King avatar.” In King’s novel, Bill also writes screenplays, which explains McAvoy’s willingness to discuss the subject. Other actors are cagier, reluctant to spoil the deviations screenwriter Gary Dauberman (the Annabelle movies) has made from the novel. “It’s not the same as the book,” says Hader about his character’s post-Derry life. “But it’ll be a real mindblower.” Is he a porn star? “Yeah,” Hader jokes. (We think.)

The Muschiettis cast Jay Ryan (Top of the Lake) as Ben, Andy Bean (Swamp Thing) as Stanley, and Isaiah Mustafa (Shadowhunters, the Old Spice commercials) as Mike, the one member of the Losers’ Club to remain in Derry, who now works as a librarian. “Mike sees how Derry is very special in a dark way,” says the actor. “He’s trying to figure out what the hell’s going on in this town and what he can do to put an end to this cycle. It’s an obsession for him.” Mike needs the help of his childhood friends for a repeat match against Pennywise, who was beaten but not destroyed at the end of 2017’s It. The catch? All the other members of the Losers’ Club don’t remember the traumatic events of their childhood. “When you leave Derry, something happens where you forget it all,” says McAvoy. “I think it’s like a [power] of Pennywise’s. Because if everybody could remember what he gets up to every 27 years through history, we’d go, ‘Hey, Derry’s really f—ed up, we should do something about that. We should send in the f—ing Army!’” 

The Losers’ Club reconvenes in Derry, where the members size each other up at a Chinese restaurant. “We had so much fun,” says Chastain of shooting the sequence. “We literally sat, pretending to drink shots and eat Chinese food, for two days. Andy would yell stuff out like ‘Take a shot with your mouth, no hands!’” Though she’d previously worked on two other films with McAvoy and shared one scene with Bill Hader in The Disappearance of Eleanor Rigby: Them, the actress “didn’t know anyone else. As the Losers were getting to know each other again, we were all getting to know each other [as actors].”

Muschietti also gathered the young performers who played the Losers’ Club in the first film for scenes depicting the recovered memories of  the adult characters. “Instead of us just standing around going, ‘Oh, I remember that time,’ we get to show it to the audience,” McAvoy tells EW. “Which is great, because that would be real sad if we had to say goodbye to that cast that the audience across the world fell in love with. And actually, in a weird way this movie resembles the structure of the book, in that it goes back and forth.”

As for Skarsgård’s clown, well, it turns out that after losing out to the Losers in the first film, he is really not smiling — at least not on the inside — this time around. “He’s scarier and he’s angrier,” says the actor. “There’s a couple of very brutal things in the film.”

Sounds like you should leave the wine at home.

-Reporting by Anthony Breznican

Get ready for Comic-Con 2019 with EW’s special It Chapter Two issue. Buy one — or both — of our collector’s covers featuring the Losers’ Club and Pennywise. Don’t forget to subscribe for more exclusive interviews and photos, only in EW.

Related content:

It Chapter Two is taking Pennywise to San Diego Comic-Con

It Chapter Two trailer decoded: HIdden horrors lurk in the new teaser

Pennywise will be a more vengeful and bloodthirsty clown in It Chapter Two