Meet our Fall Cover Star: Jessica Chastain

Throughout her considerable body of work in film, Jessica Chastain has regularly been called upon to play the roles of complicated, powerful, and strong-willed women. Her scene-stealing performances have earned the actor ample recognition and numerous accolades along her storied Hollywood career, including two Oscar nominations and a Golden Globe win.

“I ask myself: is this something I’m going to be learning from, something I’ve never done before? What am I putting out into the world?” says the 42-year-old by phone. “It doesn’t mean that the character has to be a hero—but am I moving society in a positive direction with whatever I’m putting out in the world? Those are the questions I ask myself now.”

This September, Chastain returns to the big screen in the blockbuster scare IT Chapter Two, the sequel to Argen-tinian-born brother and sister duo Andrés (Andy) and Barbara Muschietti’s 2017 hit adaptation of the beloved 1986 Stephen King novel.

Jacket and shoes by Saint Laurent; earrings by Chopard.

As the undisputed master of horror fiction’s magnum opus, King’s It is quite the tome. Clocking in at well over 1,000 pages, the novel alternates between past and present timelines, and tells the coming-of-age tale of a gang of kids who face Pennywise, a homicidal dancing clown haunting an entire community in small-town America. The shape-shifter can transform into its victims’ worst nightmares—feeding on both their fear and their flesh. With such a heavy hardback to work from, it’s no surprise that the sibling filmmakers would decide to split King’s narrative across two separate films, with their 2017 adaptation having focused solely on the childhood arc.

When audiences last saw King’s gang of seven preteen protagonists—the self-described “Losers’ Club”—on the silver screen, the 11-year-olds had successfully warded off Pennywise and made a blood oath to come back to fight if the supernatural monstrosity ever returned to their hometown. Set 27 years later, duty calls in IT Chapter Two.

Chastain plays grown-up Beverly Marsh in the sequel, a role acted by teenage newcomer Sophia Lillis in the first film. Turns out, she was the dream choice as the adult doppel-gänger from the get-go.

Jacket by Chanel; earrings by Cartier.

“Before they started shooting the first instalment, Andy sent me a picture of Sophia and myself side-by-side and wrote, ‘What do you think?’ Probably because Sophia actually looks a lot like I did as a child,” reveals Chastain. “That was my first thinking of like, ‘Oh, okay! I might be doing this film later on.’”

It was a character role the lauded actor was thrilled to land. “I was excited by it,” she expresses. “Especially after I saw the first film. Andy and Barbara showed it to me, and I thought that they did such an amazing job with it.” Chastain was far from alone in this sentiment, as the spooky thriller’s walloping debut shattered box-office records, earning it the title of high- est-grossing horror movie of all time.

When audiences are introduced to young Beverly in the first movie, they encounter a tough but damaged red-headed tomboy. The strongest of the Losers’, and the glue that appears to bind the group together, Beverly is confident, courageous, and quite the badass. At the same time, though, she’s battling a very corrupted girlhood. Every day, Beverly goes home to her biggest fear and monster: her abusive and predatory father. In addition, she deals with classmates who constantly slut-shame her.

Jacket, cardigan, top, and skirt by Max Mara; necklace by Cartier.

Beverly’s coming-of-age narrative is no doubt challenging in the first film and, according to Chastain, her adult story is just as troubled. “When we meet Beverly, she’s working as a fashion designer and is still perpetuating this pattern of abusive relationships. She’s still involved in it,” says Chastain.

In preparation for the role, the seasoned actor—a lover of psychological horror films “where the monster is somehow in your head”—looked to Lillis for guidance. “I [watched] Sophia’s performance in the first one. I wanted to copy what she was doing, especially her little movements and mannerisms, to honour the beautiful performance she gave in the first chapter.”

Working on IT Chapter Two, which was filmed just outside Toronto last year, was no easy feat. “This was a very, very physical shoot. I didn’t have a day off because all of my section was front-loaded in the schedule,” explains Chastain, whose rigorous timeline found her on set for nearly two and a half months straight. “I made sure I had a good lunch,” she laughs. “I knew we were going to be working so much.”

Jacket and skirt by BOSS; shoes by Christian Louboutin; earrings by Chopard; ring by Cartier; ring by Bulgari.

The fact that scary movies require intense performances from their casts to emote fear made filming doubly taxing. “I can tell you that [horror] is very emotionally demanding—moreso, I think, than other genres, because your character is uncomfortable most of the film. You’re emotionally uncomfortable, but also you’re in situations that really challenge who the character is physically. I was absolutely exhausted at the end of the shoot,” Chastain elaborates.

IT Chapter Two marks the third horror film on the multifaceted talent’s acting CV. She played the goth-rocker girlfriend of Game of Thrones actor Nikolaj Coster-Waldau in the 2013 ghost story Mama (a film that director Andy Muschietti also helmed), and starred opposite Tom Hiddleston and Mia Wasikowska in Guillermo del Toro’s Crimson Peak in 2015.

Jacket and skirt by Prada; earrings by Chopard; ring by Cartier; ring by Bulgari

When asked which project she considers to be her breakthrough into the Hollywood machine, Chastain credits a 2006 staged reading she did of playwright Oscar Wilde’s biblical tragedy Salomé at Los Angeles’s Wadsworth Theatre. Back then, Chastain was a 29-year-old unknown Juilliard graduate armed with classical acting chops and starring alongside legendary actor Al Pacino, who also directed the production. “It was such an incredible showcase for me. Here I was opposite Al Pacino as the title character of the play,” relives Chastain. “It was such a great introduction to a bunch of agents and executives in Los Angeles where, all of a sudden, I was being seen for projects that I normally wouldn’t have been seen for.”

As for her first major movie appearance, that milestone goes to director Terrence Malick’s 2011 poetic essay The Tree of Life, in which Chastain starred alongside Brad Pitt and Sean Penn. “I was a complete unknown acting opposite Brad Pitt, who was at the height of his stardom. I remember walking on that red carpet holding hands with Sean Penn and Brad Pitt, and it was like the birth of my career.”

Jacket by BOSS.

Whether demanding gender pay equity on projects or fighting sexism in storylines, Chastain has been a long-time advocate of women in film, both onscreen and behind the scenes. Wonderfully outspoken, the indefatigable voice also advocates for racial and, most recently, LGBTQ+ equality, making her a fearless force for change in Hollywood and beyond. For the actor, using her star power to fight the good fight by drawing attention to the entertainment industry’s double standards is like second nature. “It’s just part of who I am,” she says. “If I see a situation or have a platform that someone else may not have, I feel like it’s my opportunity to share it—to use my platform to amplify the voices of others. I’ve just always felt that way.”

And Chastain is determined to make female empowerment and inclusivity part of her growing career. In 2016, the actor founded her very own production company, Freckle Films, as a major push toward developing more female-driven stories. Focusing on nurturing and supporting female talent across all aspects of production, the women-led company is made up of business partner Kelly Carmichael, a former Weinstein Company and Miramax production exec, and their colleague Arianna Anderson.

“My company, honestly, is me, Kelly, and Arianna in my living room,” she explains—and it’s been a mammoth undertaking for the American actor, to say the least. “We’re really swinging for the fences here. We’re doing a lot, and I hope that as we grow, we’re able to grow in such a way that we can have the support system of more people. Because I’m self-financing my office, my employee salaries—all of that.”

The business idea struck Chastain following an acceptance speech she gave at the 2015 Critics’ Choice Movie Awards. For the first time ever, an MVP award was given out, and Jessica was the recipient for her standout character portrayals in four critically acclaimed 2014 movies: A Most Violent Year, The Disappearance of Eleanor Rigby, Interstellar, and Miss Julie. “I didn’t quite know what to talk about, so instead of talking about one particular film, I talked about our need for inclusivity in our industry,” she notes.

Top and jacket by Burberry; ring by Cartier.

Her powerful words got people buzzing, especially in the media, which led Chastain to put her money where her mouth was. “Right after that, I went to London to do some press for A Most Violent Year, and a lot of the journalists were talking about the speech and how important it was. [They] were asking how I was going to put it into practical application,” she discloses. “So from those conversations, my production company was born.”

Chastain and her small-but-mighty team definitely have some noteworthy movie projects underway. First up: the action-packed, all-female spy thriller 355, which commenced filming this past summer and sees Chastain join- ing Penélope Cruz, Lupita Nyong’o, and Fan Bingbing on-screen. The biggest sale at the 2018 Cannes Film Festival, Chastain spearheaded a multi-million-dollar deal—the biggest sale at the 2018 Cannes Film Festival—that ensured all the actors in the espionage flick would be paid equally, plus get a share of the profits.

Later in the year, the Freckle Films banner will also fly above The Eyes of Tammy Faye, a biopic that depicts the rise, fall, and redemption of television evangelist Tammy Faye Bakker. “I’m so blown away with Tammy Faye Bakker and what she brought to religion, what she brought to her idea of what inclusivity is,” says Chastain, who is set to star as the singer.

What’s it like stepping behind the scenes and into the shoes of a producer? “The challenge is every day,” says Chastain. “When you’re putting together a movie, it always feels like it’s going to fall apart.” It’s a realization the actor grew to know quite well while filming IT Chapter Two, a project whose producer provided Chastain with invaluable experience and knowledge. “I learned a lot about producing from Barbara. I sat with her every day when we were making [the film], seeing the difficulties she was facing and the problems she was always solving,” recounts Chastain. “You just have to keep moving forward and not give up. I’ve learned so much about that kind of persistence.”

Photography by Juco at Art & Motion

Styling by Elizabeth Stewart at The Wall Group

Makeup by Kate Lee at The Wall Group

Hair by Renato Campora at The Wall Group

Manicure by Shigeko Taylor at Star Touch Agency using Dior

Art Direction Elena Viltovskaia