When the Danish film The Guilty premiered at the 2018 Sundance Film Festival, much of the audience exited the screening in a state of adrenaline overload or distress. Jake Gyllenhaal, on the other hand, felt inspired: He couldn’t help but wonder what an American version would look like, and he soon took it upon himself to find out. The end result, shot over the course of just 11 days, stars Gyllenhaal as a cop who’s on desk duty as a 911 operator when a frantic woman (played by Riley Keough) calls in to report that she’s been abducted. Then, she promptly hangs up. For W’s annual Best Performances issue, Gyllenhaal shares why he was so compelled to adapt The Guilty and recalls an entirely different anxiety-inducing experience: his early on-set encounter with Brad Pitt.

Tell me how The Guilty came to you.

I originally saw it as a Danish film, out of Sundance in 2018. I just immediately fell for it and thought, Wow, this would be so interesting in an American context.

So I begged and begged and begged the filmmakers for the rights, then went on my merry way. After a long negotiation process, I decided to develop it into an American version. I just thought that it was really prescient in the way it talked about all of our systems, how they were broken. It’s a movie about assumptions—what we project onto other people when we can’t see them, and why we do that. About how much help I think so many people need, and maybe they can’t ask for or feel ashamed to ask for. There are so many stigmas around mental health, and I don’t think many of our systems are helping with so many of the issues that people have and the pain that they feel. So the movie was thrilling and super entertaining, but it allowed for a conversation about all that as well.

What movie makes you cry?

Searching for Bobby Fischer. Every time, without a doubt. There’s a moment where he and his dad play chess for the first time, and his dad sort of underestimates him. Everything about it, I just love. Just an extraordinary cast, and so beautifully shot by [cinematographer] Conrad Hall and [director] Steven Zaillian. I think it’s one of those movies of a time that doesn’t get made anymore, unfortunately.

I mean, you could say The Guilty feels like it has the same kind of independent spirit.

It does, but it’s a big movie. Searching for Bobby Fischer feels big. The score is huge. It’s a little boy’s point of view, but it feels like you have the same composer as Braveheart. A little boy [can] have the same feelings as somebody fighting in a war with spears and swords and their hands.

When was the first time you sang onstage?

I played the Scarecrow in The Wizard of Oz when I was 10 years old. It felt oddly comfortable, which is when I knew I needed help. [Laughs] And here I am, 30 years later, doing the same shit, man. But no, I really do remember feeling elated, understanding how to sort of push and pull the energy of an audience—even though they were in the dark to me—which is so fun. And [I remember] feeling confident in that space. As a kid, I was so insecure. But when I got up onstage, which is such an odd place to feel confident, it felt like an expression. It brought me so much joy. I grew up in a very serious family, and so to feel that kind of joy and then to also see the response of an audience, their own joy, even at that age. Onstage, and then when you come off it, too.

Have you ever been starstruck?

Oh yeah, absolutely. I was starstruck with Mandy Patinkin when he came to see Sunday in the Park With George, a show I did. He originated the [title] role and basically created the role. And I was definitely starstruck when I first met Brad Pitt on the set of The Good Girl. I was working with Jennifer Aniston, who was his wife at the time, and there were a lot of very racy scenes. I remember putting my hand out to shake his, and accidentally hitting the door. He said, so confidently and kindly, “Well, you have another one. It’s all right.” He was very, very, very sweet to me, and it was actually a really lovely exchange. But, yeah—I was starstruck.

What was your favorite film when you were growing up?

Initially, I was forced to watch Gigi, and so it slowly became my favorite film. But then it was Point Break. Doesn’t that sort of encapsulate me?

Gallery Link:
Photoshoots & Outtakes > Sessions > 2022 > Session 001 [W Magazine]