Jake Gyllenhaal Reconsiders

Gyllenhaal next appears in Ambulance (out April 8). It’s about a close-knit team of bank robbers whose plan collapses as soon as it starts, leading to a movie-length car chase that, yes, involves an ambulance and, yes, is directed by Michael Bay. Eiza González and Yahya Abdul-Mateen II costar. “The other day, Eiza and I were talking about the pronunciation of names,” Abdul-Mateen tells me, “and we joked that no one has a problem pronouncing Jake’s name, because we’ve known it all our lives. He’s a Hollywood staple.”






But that’s the effect of Gyllenhaal’s long, unpredictable career. It feels like he has been around forever. He was still in high school when he launched to leading-man status, as a rocket-building West Virginian in October Sky. His breakthrough performance came two years later, in 2001, as the morose, maybe schizophrenic Donnie Darko. It remains one of his most recognizable roles. Someone told him recently they’d only seen the movie while stoned. “Oh, great,” he said. “Try watching without it. See your experience.” While he doesn’t love revisiting his own movies, that’s one he’ll stop to watch and think, Oh, right. Oh, wow.

Darko’s personality overlapped with his own at the time: “philosophical and angsty,” as he puts it. By then, cinema’s superhero era had just begun; while many up-and-coming actors were following the money to Hulk and the Star Wars prequels and other modern classics, Gyllenhaal set down a different, broodier path. Though he only realized it years later, he was driven by a want to prove—to himself, but also to his Hollywood peers and power brokers—that he took the job seriously, he planned to do it for a while, and he’d dig as deep as he needed in order to understand it.

He studied his costars. “The thing about Jake is that he’s so emotionally intelligent,” says Maggie, his older sister by three years. “He’s able to read everything that you put down.” On the set of the 2002 drama Moonlight Mile, he watched Dustin Hoffman knock out sets of triceps dips on a walker to raise his heart rate before a scene. “I was like, ‘Oh, this is what a good actor does,’ ” Gyllenhaal says. At the end of the shoot, Hoffman gave him a copy of Konstantin Stanislavski’s An Actor Prepares, inscribed with a message—“You’re good, but you’ve got to get better”—and a walker of his own. During the filming of 2005’s Brokeback Mountain in the Canadian wilderness, Gyllenhaal took note of Heath Ledger’s meticulous, intense technique. “While we were on set, Heath would get in his moment, and he would stay in his moment,” he says. Both he and Ledger received Oscar nominations for their performances, as two sheepherders in love.

Gyllenhaal tried his hand at massive productions. “There have been times when I’ve done the George Clooney rule of ‘Do a big one, then one for you,’ that whole thing,” he says. When filming began on The Day After Tomorrow, the 2004 summer blockbuster with climate change as the foe, he approached Dennis Quaid to work through their scenes, and Quaid “was like, Chill out. Chill out, bro.”

The 2009 Afghanistan-war movie Brothers, seen by few and little remembered, marked a turning point for Gyllenhaal, changed his entire approach to acting. With director Jim Sheridan’s encouragement, costar Tobey Maguire prepared by immersing himself in the world of veterans suffering from PTSD and anywhere else he deemed necessary to find meaning and honesty and truth. “I was influenced by watching Tobey do that,” Gyllenhaal says, “so I started to do that, too.”

He did two more big ones, both released in 2010—the rom-com Love & Other Drugs and the so-bad-it’s-funny-oh-wait-it’s-just-awful Prince of Persia—and then, until the end of the decade, he mostly did ones for himself. He sought out renegade directors who’d offer him the leeway to bore as deeply into his roles as he thought he needed. He even handpicked Duncan Jones, David Bowie’s son, for the sorely underrated time-warping thriller Source Code. The press couldn’t get enough of the lengths Gyllenhaal would go to in order to prepare. To play an upstart videographer of other people’s misery in 2014’s Nightcrawler, he ran up to fifteen miles a day, chewed gum instead of food, and shed thirty pounds to achieve the look of a hollowed gourd. Then, for his next role, as a down-and-out boxer in 2015’s Southpaw, he packed on muscle and went up to 180. “My God, that’s extreme. That’s dangerous,” says Southpaw director Antoine Fuqua. “Actors do that, you know, but Jake goes right to the edge.” He adds, “And sometimes you have to pull him back. He’s like a stick of dynamite.” Denis Villeneuve, who directed him twice, back-to-back—in 2013’s Prisoners and 2014’s Enemy—characterizes Gyllenhaal as “a wild horse.”

“I don’t know anybody who would say, ‘You know what Jake is? Incredibly laid-back about work,’” says Jeanine Tesori, a theatrical composer and producer who collaborated with him on his Broadway-musical debut: Stephen Sondheim’s Sunday in the Park with George, in 2017, about the agonies and the ecstasies of the artistic life. Gyllenhaal was a natural onstage; he received a Tony nomination in 2020 for his subtly heartbreaking performance in the play Sea Wall/A Life. In some ways, he enjoyed it more than movie acting; in theater, he could see—feel—the audience’s reception of his every performance. Maggie recalls seeing him while he was in his first Broadway play, Constellations, in 2015. He and costar Ruth Wilson would “be out every night, having a great dinner, drinking a bottle of wine, no stress about making sure that every single atom of himself was focused on the work. I loved seeing him so carefree. I preferred hanging out with him when he was like that.”