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‘It: Chapter Two’: Dream Casting the Stars Who Should Join Jessica Chastain in Horror Sequel

With the Oscar nominee reportedly set to star in Andy Muschietti's much-hyped sequel, we cast the rest of the now-adult Losers Club, one that just might have more star power than previously expected.

“It”

Brooke Palmer

When “It: Chapter Two” arrives in theaters next September (yes, you’re going to have to go a whole other Halloween season without some fresh Stephen King-created blood), it will come complete with a brand-new cast of now-adult Losers. The film will jump ahead 27 years — as is the wont of dimension-hopping demonic villain It, who likes to reappear in good ol’ Derry, Maine on a 27-year cycle — casting the cute kiddos who made the first film so memorable as jaded adults hellbent on finally killing the hellbeast that made their tween years such a nightmare. (For fans of the talented kids who starred in last year’s horror hit, never fear, as director Andy Muschietti has already promised that the younger Losers will be back for some flashback scenes that help bridge the first film with the second.)

As has long been rumored, Jessica Chastain is the first cast member on deck, as the actress is in negotiations to join the film as a grown-up Beverly Marsh. Casting someone like Chastain is big news on its own, but it also adds a certain expectation to the rest of the cast: here’s a film that is capable of snagging a two-time Oscar nominee for one of its key roles. The rest of the cast needs to be up to snuff. Who should form the core of our adult Losers Club? We’ve got some ideas.

Jessica Chastain as Beverly “Bev” Marsh (originally played by Sophia Lillis)

In King’s book, Beverly gets her wish, escaping Derry for big city life in Chicago, where she’s a successful fashion designer. Yet the scars of her early life run deep, and adult Beverly has spent much of her life in abusive relationships that harken back to her childhood with her evil father. That includes her current husband, Tom Rogan, who often beats her and views her mostly as a sexual object to be controlled (and, yes, his motivations get much worse as the story goes on).

Chastain was long rumored to be in contention for the role and even told Screen Rant last November that she would love to play adult Beverly should her schedule work out. The actress is a friend and previous collaborator of “It” director Andy Muschietti, who directed her in the horror film “Mama.” “Well, I love Andy [Muschietti] and Barbara [Muschietti],” Chastain told the outlet. “I worked with them on Andy’s directorial debut, you know, his film, ‘Mama.’ His first film. And you know, Barbara is one of my best friends so…We’ll see…They’re my friends. They’re like my family. Anything that they’re doing I want to be a part of, so I hope we can make it happen.”

Jake Gyllenhaal as William “Bill” Denbrough (originally played by Jaeden Lieberher)

Like Beverly, Bill gets out of Derry and finds professional success far away from his childhood home (in King’s book, he’s living in England when he’s called back, where he’s busy writing his own tales). He even has his own relationship that looks — at least from the outside — to be happy and loving, thanks to his marriage to film star Audra Phillips (bonus casting: Audra looks a lot like Bev, so why not line up a sweet supporting part for fellow redheads Bryce Dallas Howard or Amy Adams?).

Bill is a tricky role. As a kid, he was obviously and understandably in bad shape after the disappearance of his beloved baby brother Georgie, but things turn around for him as he matures (that stutter? it even goes away for awhile). As an adult, Bill looks like one of the more put-together of the grown-up Losers, and he again emerges as the group’s leader and perhaps its most outwardly brave member. It’s a part that requires someone able to project surface-level happiness while also tapping into deep emotional issues.

So, basically, “Demolition,” but good? We jest! “Enemy,” but more accessible.

Chris Pratt as Benjamin “Ben” Hanscom (originally played by Jeremy Ray Taylor)

Ben sheds his baby fat and goes on to become an internationally renowned architect (hey, those maps did pay off) in the dead center of the country: Nebraska. Like Bev and Bill, he grudgingly returns to Derry, knowing that he has to finally help defeat It once and for all. He’s still got all his sweetness and smarts, and who better to marry hangdog charm with relatable comfort than Pratt?

Bill Hader as Richard “Richie” Tozier (originally played by Finn Wolfhard)

The Internet dream casting machine has long been in agreement on exactly one piece of potential “It: Chapter Two” casting: Bill Hader has to play Richie Tozier. Even Wolfhard himself as singled out the comedian and actor as his obvious predecessor, and the kid is dead on.

As an adult, Richie has channeled his squeaky voice and whipsmart cracks into his own solid career, becoming a popular disc jockey in Los Angeles. Of course Hader has the comic chops to play King’s beloved “Trashmouth,” but the former “SNL” star has also proven his ability to take on darker material with ease. Look no further than his turn in “The Skeleton Twins” for proof of a lingering dark aesthetic that could be positively unleashed by a role in a true-blue horror film.

Tom Hiddleston as Stanley “Stan” Uris (originally played by Wyatt Oleff)

No spoilers, but we won’t be seeing too much of adult Stan in “Chapter Two,” but he will likely make a memorable impression in the first moments of the new film. Per “It” lore, Stan doesn’t make it back to Derry, but he will probably make off with one of the film’s more chilling plotlines, one that will explain his absence.

Chastain and Hiddleston are old pals, having previously starred together in Guillermo del Toro’s ambitious “Crimson Peak,” so it’s possible the actress could help cast him for the role, one that wouldn’t require much in the way of time but would give him the kind of splashy publicity he’s in need of these days. And, face it, Oleff looks just like a mini-Hiddleston. It’s eerie.

David Oyelowo as Michael “Mike” Hanlon (originally played by Chosen Jacobs)

While Muschietti’s film tweaked some large parts of Mike’s story — in King’s book, it’s Mike who serves as the unofficial Derry historian, not Ben — “Chapter Two” will likely have to reset some of those changes, as Mike is the only one of the Losers to stay behind in Derry, where he continues to trawl the town’s history to uncover the truth about It. He’s also the one who calls back the rest of the far-flung Losers when it’s time to take down It during his latest cyclical return to their hometown. In short, it’s a big, important role, and one that requires the kind of gravitas that Oyelowo so assuredly possesses in every role.

Adam Scott as Edward “Eddie” Kaspbrak (originally played by Jack Dylan Grazer)

Much like Bev and Bill, Eddie’s grownup life looks to be a good one: he runs his own limousine company in New York City, and he’s even got a loving wife at home. Oh, about that wife. Aside from It, Eddie’s childhood was haunted by another serious monster: his mother, who suffered from Munchausen syndrome by proxy and used it as a way to trap hypochondriac Eddie into believing he was always sick (or just about to be).

While the first “It” saw Eddie breaking from his mother’s grasp, King’s novel lets on that he’s still reeling from the effects of a complicated childhood, and his wife Myra is just as controlling as he mother was. Scott can nail the nervous nature of Eddie, along with his often (very funny) bond with Richie, while adding in the kind of jittery fear that informs so much of his life.

Jesse Plemons as Henry Bowers (originally played by Nicholas Hamilton)

Like Hiddleston and Oleff, the Emmy nominee’s unique face invokes a grown-up Hamilton to an almost chilling degree. As in the first film, Bowers will likely emerge as the Losers’ most prolific human bully, and one made all the more powerful by some help from no less than It. Young Henry was driven totally insane by the end of the first half of King’s book, and was eventually convicted of the murder of his dad (which, oh yes, he did) and blamed for many of It’s other crimes. Sent away to an insane asylum, he’s busted out by It, just as the Losers are heading back to Derry.

Plemons can do dark, but playing a grown Henry Bowers could free him up to take on his most challenging role yet, the kind of signature work that would supersede even the happiest of “Friday Night Lights” and “Fargo” memories.

Bill Skarsgard as Pennywise the Dancing Clown (originally played by Bill Skarsgard)

"It"

“It”

Warner Bros.

Why mess with perfection, especially when that perfection is playing an ancient evil being that can cross time, space, and dimension, all while taking on any appearance it so chooses?

“It: Chapter Two” arrives on September 6, 2019.

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