Jake Gyllenhaal pulls his glasses out of his jean jacket pocket, the Coke bottle lenses in them strong enough to correct his 20/1250 vision. Yes, you read that right. These are not Internet Boyfriend glasses, to be styled with a fuzzy cardigan and a rakish smile. These are I Literally Can’t See glasses. Looking through them with normal vision feels like being on some sort of a hallucinogenic.

Gyllenhaal, 43, has been wearing intensive corrective lenses since he was about 6. Born with a lazy eye that naturally resolved, he’s still legally blind. “I like to think it’s advantageous,” he says. “I’ve never known anything else. When I can’t see in the morning, before I put on my glasses, it’s a place where I can be with myself.” He has used his blindness sometimes to help him as an actor — when he was shooting a difficult scene in the 2015 boxing movie Southpaw, one in which police tell his character that his wife has died, Gyllenhaal removed his contacts to force himself to listen more closely.

It’s almost a relief to learn that Gyllenhaal, who seems to have hit the lottery in so many facets of life — talent, looks, a show business family — has some sort of weakness. Sure, he may have chiseled down to 5 percent body fat to play an ex-UFC fighter in Road House opposite Conor McGregor, and he may be in the midst of preparing to perform Shakespeare’s Othello on Broadway with Denzel Washington, but the man is human.

Gyllenhaal has just flown into Los Angeles after hosting the season finale of Saturday Night Live, an episode in which he fulfilled a childhood dream of performing a Boyz II Men song (“Every car drive, every shower,” he says of his relationship to the ’90s R&B band) and played an unhinged version of Fred, the ascot-wearing cornball from Scooby-Doo. He’s just appeared at Amazon’s upfront presentation to tout a Road House sequel— more than 50 million viewers tuned in to see the action movie reboot in its first two weekends on the streaming service this spring, a record for movies produced at the studio. And he’s got a new courtroom thriller series, David E. Kelley’s Presumed Innocent, hitting Apple TV+ on June 12, in which he plays an attorney who might have killed a woman.

If there’s a throughline to this eclectic recent résumé, Gyllenhaal says, it’s that he has been actively seeking projects that “freak me out a bit … The feeling I want to have is, can I do it? That it’s going to ask of me things that I don’t know about myself yet.” Sometimes the things he learns are uncomfortable — like that he can get a staph infection from pressing his hand down on a bunch of broken glass, which happened after shooting a fight scene in Road House. And he’s prepared for this philosophy of extreme challenge to backfire someday. Performing his first Shakespeare play ever in a Broadway production with Washington is a pretty high-stakes way to find out if he has a knack for the Bard. “Maybe I should have started with a sonnet,” he says.

But for all the intensity of focus Gyllenhaal has brought to his work over the years, lately he is working on mastering something he can’t achieve by grinding out another set at the gym or drilling his lines, something more elusive. More than 30 years into a career that started when he was 10 with a role in City Slickers, Gyllenhaal is — finally — learning how to navigate life onscreen and off with a little more peace. That has meant investing in his relationships, including with longtime girlfriend Jeanne Cadieu, and taking some roles for the pure pleasure of them.

“There are movies I’ve made that people have said to me, ‘Man, intense. That was great. It was tough,’ ” Gyllenhaal says. “And there have been many different times where I’m like, ‘Wait, what’s it like to make a movie and be like, ‘That was just fun?’ Road House was definitely that.”

It might seem like a stretch to call getting punched in the face “fun,” but Gyllenhaal is referring to the exuberant spirit of the endeavor. The actor references the film he says he has watched more than any other in his life, 1991’s Point Break, which he has seen hundreds of times. To him, Patrick Swayze’s and Keanu Reeves’ performances in the surf-cop action movie reflect the joyful commitment of true artists. “To deliver a line that goes into a trailer, with the right gusto and belief, and even with the absurdity of it, it’s a mastery,” Gyllenhaal says. “There’s that thing, the camera’s pushing in and I’m always like, ‘Oh wow, this is when you see Bruce Willis do the line, the thing. And now I’m doing the thing. Like, oh God.’ ” In Road House, for instance, before his character’s first time knocking out a rowdy bar customer, he asks genially, “Before we start, do you have insurance? Like, your coverage good? Do you have dental?” It’s the kind of action-comedy moment Gyllenhaal grew up watching and only now truly appreciates as craft. “It requires this ease, but focus,” he says. “I’m in awe of people who can do it.”

Before he could learn to summon the kind of relaxed bravado those moments call for, Gyllenhaal had to learn to tap the brakes a bit. A revelation of sorts came while he was making Southpaw and his director, Antoine Fuqua, actually asked him to train less. “He started trying to do two-a-days and [working out] on Sunday,” Fuqua says. “I’d have to tell him not to because he was burning himself out. But he was so focused and intense about it. Not just as an actor, but as a person, he fully committed.” While making that movie, Gyllenhaal says, he was having trouble figuring out how to play a particular scene, and so he called his longtime acting coach, Penny Allen. “She said, ‘You’ve lost your imagination,’ ” Gyllenhaal recalls. ” ‘That’s really all you need to do this work.’ And I was like, ‘Oh, shit.’ ”

Gyllenhaal’s first interest in acting came from watching his sister, Maggie, in a junior high school production of South Pacific. “I worshiped her, and she was like, ‘Go away,’ ” Jake says of his childhood dynamic with Maggie, who is three years older and now in the midst of directing her second feature, a modern spin on Bride of Frankenstein, for Warner Bros. “Clearly we came out ready to go,” Gyllenhaal says of his and Maggie’s show business trajectories. “My sister has always been brilliant. What it did was present something to me that I inevitably would always be chasing. She takes a step and does something and I’m like, ‘Whoa, holy shit. All right, I’m going to try this.’ ” Maggie remembers Jake as a kid as “a bolt of electricity that used to make my friends and I laugh so hard that we would cry.” The siblings grew up in L.A.’s Hancock Park. Their father, Stephen Gyllenhaal, is a director, primarily of TV movies, and their mother, Naomi Foner Gyllenhaal, a screenwriter who was nominated for an Oscar for 1988’s Running on Empty when Jake was 8. His parents’ careers gave Gyllenhaal a close-up view of the industry and its larger-than-life figures. Asked about a small choice he makes in Presumed Innocent, to have his character hold his glasses by tucking them midway down a buttoned dress shirt, Gyllenhaal casually says it’s a habit he observed in Paul Newman, who happened to be his godfather. “He also wore them hanging from his ear and stuff like that.”

Peter Sarsgaard, Maggie’s husband of 15 years, has acted with Jake in multiple projects, including Presumed Innocent, and cites his brother-in-law’s unusual sensitivity to his environment, beyond the norm even for an actor. “He’s the person who knows that a fight’s about to happen before it happens,” Sarsgaard says, “that person who can feel the change in the emotional weather before other people do.” Gyllenhaal agrees that he is “hyperaware” and attributes that vigilance to a childhood with parents who were driven, and sometimes inaccessible. “My parents were really busy and working a lot,” he says. “I spent a lot of time as a kid being like, ‘What’s that mean? What is that? Are they going?’ ” To Sarsgaard, one benefit of the Gyllenhaal kids’ entertainment industry upbringing is an unusual sophistication about the business. “It seemed that they had a kind of, not just advantage in terms of getting jobs but in terms of knowing what the job was — both of them, from the day they were born,” Sarsgaard says.

After a few acting parts as a kid, including in some of his dad’s projects, Jake’s breakout came at age 20 in the 2001 cult hit Donnie Darko, in which he played a troubled teen who talks to a giant rabbit named Frank. His early career was defined by roles in serious-minded films for prestigious directors, most notably 2005’s Brokeback Mountain, in the role of a closeted cowboy that earned him an Oscar nomination and spot in the “Is he gay?” leading man gossip rotation, which he called “a huge compliment.” He worked with Sam Mendes, David Fincher and Denis Villeneuve, who calls Gyllenhaal “a perfectionist.” Fuqua compares the actor’s concentration to that of his Training Day star, Washington. “There was a little bit of a chip on the shoulder with Jake,” Fuqua says. “Not in a negative way. He just really cares. At times, I think people don’t understand him. It’s not about power or control. He just wants it to be the best it can. He’s always thinking.” Asked what he thinks Gyllenhaal and Washington’s collaboration will be like on Othello, Fuqua takes a long pause before answering, finally: “Intense.” There’s that word again.

On the heels of his acting coach’s observation that he had lost his sense of imagination, Gyllenhaal began reinventing himself artistically. He founded his Nine Stories production company and used it to back small but powerful movies like Paul Dano’s 2018 directorial debut, Wildlife, and The Guilty, a remake of a Danish thriller for which he recruited Fuqua to shoot with him during the pandemic. He also started producing theater, including a 2017 revival of Stephen Sondheim’s intricate musical Sunday in the Park With George, delivering the lead performance in a singing voice The New York Times called “a revelation.”

“I’ve never seen him happier than when he’s onstage singing,” Maggie says. “Out to dinner every night after the show, alive and free and happy.” As a film actor, he started to lean into weirder fare, playing an over-the-top TV host in Bong Joon Ho’s Okja, in a performance that critics either loved (“charmed,” said The Atlantic) or hated (“antic and abrasive,” said The New York Times) but agreed was loose and new, and Dan Gilroy’s Velvet Buzzsaw. He also started making action movies for macho directors like Michael Bay and Guy Ritchie.

Road House, the apotheosis of Gyllenhaal’s mid-career action era, has an amusingly shallow origin story: He and director Doug Liman ran into each other at a 5K they were both running on Martha’s Vineyard during the pandemic. Gyllenhaal had been spending lockdown doing a lot of biking and was incredibly fit, and Liman decided he wanted to make a movie with him with his shirt off. At a time when even event movies are struggling in theaters, the reboot of the 1989 cult hit became proof-of-concept for the idea that an action movie can become a cultural moment without ever playing in a theater. Though Liman complained publicly about Amazon’s decision to premiere Road House on its streaming service, Gyllenhaal says that decision was not a surprise. “As soon as I knew that it was going to definitely be streaming, which Amazon was very clear about, I was like, ‘Let’s go! Can this movie be an example as something that can reach an audience and still make its way to the zeitgeist?’ “

Road House brought together divergent audiences, with fans of figures like McGregor and Post Malone, who has a cameo as a fighter, and a seemingly ubiquitous marketing campaign that included promotions through UFC and a premiere at SXSW. On his Instagram account, Gyllenhaal shared videos of his preparation, from pushups to ice baths. That was partly to help market the movie and partly to document the transformation for himself. “I wanted to record it because I was 41 getting in shape and doing all this stuff,” Gyllenhaal says. “I don’t know how long I’ll get to do it that same way.”

Gyllenhaal’s appeal with women in particular helped the movie lure a four-quadrant audience, according to Julie Rapaport, head of film, production and development at Amazon/MGM Studios. “You might expect because of the title that it would be more male-skewing or perhaps the demographic who were familiar with [the original],” Rapaport says. “But it resonated just as strongly with the younger demo and with female audiences.” After Road House, Gyllenhaal’s company closed a three-year, first-look film deal with Amazon, and he’s already starting to think about how to cast the Road House sequel. In the car on the way to this interview, he says he was listening to “Willie’s Roadhouse,” the Willie Nelson Sirius XM channel, when he thought, “Wait, Willie Nelson’s got to be in this. Willie Nelson’s got to do a song with Post Malone.”

Presumed Innocent, an adaptation of the 1987 Scott Turow novel that was first made into a 1990 Harrison Ford movie, calls on Gyllenhaal to flex some different acting muscles as Rusty Sabich, a DA who ends up accused of a murder he’s supposed to be prosecuting. “Rusty is a deeply flawed and contradictory character, at times sympathetic, other times contemptible and sometimes both simultaneously,” says Kelley. Gyllenhaal puts Rusty’s issues a little more bluntly: “Every scene should be like, ‘You suck.’ And he’s like, ‘Sorry.’ ” Gyllenhaal recruited Sarsgaard to play his main adversary in the show, a rival attorney named Tommy Molto who was originally supposed to be Italian and very short (Sarsgaard is 5-foot-11 and Danish). The brothers-in-law lived together during part of the shoot, and, as sparring partners, they’re very well cast. “There wasn’t towel whipping, but I definitely enjoy giving Jake a lot of shit,” Sarsgaard says.

During the making of the eight-episode series, Gyllenhaal’s first TV show, the actor didn’t know, he says, whether Rusty was actually guilty. “You’re waiting to know which way to turn, playing the potential variations of what possibly could be,” he says. At points in the show, Rusty runs on a treadmill to deal with his stress. Because Gyllenhaal is an avid runner in his downtime, and was still in the midst of shooting Road House during the Presumed Innocent production, Rusty’s level of fitness does strain credulity a bit for a middle-aged lawyer with two kids. “They’re like ‘OK, we’re going to get you on a treadmill and we need you to be really out of breath and sweating,’ ” Gyllenhaal recalls of a particular scene. “We waited a long time for me to be out of breath. I was like, ‘I’m so sorry.’ They’re like, ‘Well, turn it up to a sprint.’ ”

Gyllenhaal has taken the next several months off to prepare for his Othello production, which will hit Broadway in 2025 under director Kenny Leon. Shakespeare is another stop on the journey of finding “the things that are really me,” Gyllenhaal says. He has enlisted a Columbia University professor to help him absorb the text and is honing the lines with an acting coach who has worked with the Royal Shakespeare Company. “It is learning another language,” he says. “I have a bit of dyslexia, too, particularly within the articles of things — like, I’ll reverse them. Many people say, ‘But you learn so fast.’ And I’m like, ‘I drill these things.’ “

For the past six years, Gyllenhaal has been dating French model Jeanne Cadieu, whom he met at a restaurant in New York in 2018. Asked when they’re going to get married, Gyllenhaal says, playfully, “I’m supposed to tell The Hollywood Reporter that? I’m not going to give you timing,” but continues, “I think we all get into that space of work, work, work, and for a long time my career took precedence, but I’m at a point in my life where I realize that family really is the only thing that matters to me.”

It makes sense that Gyllenhaal is a little guarded about his personal life when you consider that the three-month relationship he had with Taylor Swift still triggers online fan screeds some 14 years later thanks to the signature breakup song “All Too Well” that the pop star wrote about him. Swift is one subject Gyllenhaal declines to discuss — in 2022, when she released a longer version of the 2012 song, he turned off his Instagram comments. “It has nothing to do with me,” he told Esquire at the time. “It’s about her relationship with her fans. It is her expression. Artists tap into personal experiences for inspiration, and I don’t begrudge anyone that.”

Gyllenhaal and Cadieu love to cook together, and a favorite recent date was attending KCRW’s Good Food Pie Fest, where they hung out with a pie-baking drag queen named Bertha and tasted dozens of pies. “We got tickets a month and a half early,” he says. “I was like, ‘Babe, we can go! We can go to the pie contest!’ ” Gyllenhaal’s already pretty high level of enthusiasm about life seems to peak when he’s talking about food, chefs and cookbooks, and as he does so, his voice rises and speaking tempo accelerates. “Hugh Fearnley-Whittingstall — do you know him?” he asks hopefully. “Well, he leaves his gig as a chef in London and he buys a place out in the English countryside, like a little cottage, and what he does is he learns about the land and he learns about how to raise animals and how to grow things. … Yossy Arefi is an amazing baker. This book called Snacking Cakes?” This goes on for several minutes. One of Gyllenhaal’s favorite desserts is a vanilla buttermilk cake with vanilla frosting from an Arefi recipe, and it’s the dish he often chose to cap off the once-a-week cheat meals he got while making Road House. “Jake is not just, like, a guy who throws a good dinner party,” Maggie says. “He’s as gifted a cook as he is an actor. Been a gifted cook since he was a kid.”

Jake’s childhood admiration of Maggie has evolved into a mutual, ride-or-die relationship as adults, and he has a role in her Bride of Frankenstein movie. “I am not going to be that person in an interview who gets emotional about it,” he says of their relationship, “but it is really emotional for me.” When he hosted SNL in May, Jake wore a black T-shirt that said, “The Bride & Frank,” a reference to her film. This was a continuation of a practice he started when he first hosted SNL in 2007 and wore a T-shirt with the name of Maggie and Peter’s first child, Ramona, and repeated in 2022, wearing one that said, “Ramona and Gloria,” the names of their two daughters. “This time I was like, ‘What do I do?’ ” Jake says. “Oh, I’ll just do her other baby.”

His devotion to his nieces is such that Gyllenhaal co-authored a children’s book last year, The Secret Society of Aunts & Uncles, with a childhood friend. Uncledom, Sarsgaard says, is “something Jake takes very seriously. There are two different types of uncles. Uncles who have had their own children and uncles that have not had children. Right now, Jake is the uncle who has no children of his own, so he’s like 110 percent. When he has children of his own, he’ll be 95 percent.” Still intense, just a little less so.

Gallery Links:
Magazine Scans > 2024 > The Hollywood Reporter (US) | June 5
Photoshoots & Outtakes > Sessions > Photoshoots From 2024 > Session 3 [The Hollywood Reporter]