Jake Gyllenhaal

Esquire, July 2015

Five years ago, Jake Gyllenhaal, indie darling and mainstream heart throb, took stock of his life and career and decided he’d taken a wrong turn. Today he’s once again the acclaimed star of some of the most interesting films in American cinema. And in his new movie Southpaw, he delivers his most hard-hitting performance yet.

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Also read at Esquire

Photographs by Eric Ray Davidson


Jake Gyllenhaal and I are sitting across from each other at the Casa Del Mar hotel in Santa Monica. The waiter ushered us away from the brunch crowd to an isolated table in the corner, flush against the windows, looking out onto sand and sea. And it’s a postcard out there – happy surfers, skaters and bladers, the sun dancing on the waves.

Here, though, it’s another story. Jake looks disheveled, tired, and at this point, maybe even a little disappointed. He came to talk. He likes to talk. But then I asked him a question about his upbringing, and now, he seems skeptical of what we’re attempting here, this whole “interview” business.

“One thing I learned a long time ago,” he says, “is if someone has a story they want to write, they’re going to write it, and there’s nothing I can do. Maybe I can get in four or five words in a row that are mine but…”

“Do you think that’s happening here?” I ask. “That I came with this agenda and there’s nothing you can do to change it?”

“Well, is it true?”


“I’m saying it could be like that. It has been.”

“Well, let’s at least try not to do that.”

“I would love that. Believe me.”

People who work with Jake talk more than anything about his discipline, his commitment and his need to push the limits and try something new. This is what I’ve heard from four directors, two actors and a playwright. They use words like “serious”, “prepared” and “intense”. They remark on how “he really goes for it.” Apparently on set, Jake’s the one asking to do one more take and suggesting script changes to the director, even whole new scenes. As his friend, and two-time director, Denis Villeneuve, says, “it’s a challenge to work with Jake. But it’s a great challenge. He likes to push the material.”

Today, that material is this interview. Some people might approach an interview with a stranger behind a mask of politeness, making a conspicuous effort to be pleasant above all else. But Jake’s not a fan of just being “nice” for “nice’s” sake. He’s never rude, but there’s a restlessness about him, you can see his brain ticking. He wants to talk, but not about nonsense and fluff. There was half a plan to just hang out and chill, maybe take a drive or walk along the beach. But he wasn’t into it. Driving around wouldn’t help me get to know him, and that’s why I was there, surely? No, he’d sooner just talk, somewhere we won’t be bothered, if that’s all right.

So here we are – two men drinking bottled water in a deserted corner of a hotel restaurant. All the surrounding tables are empty. There’s no waiter hovering with news of today’s specials. Neither of us even have a menu. It’s as stark as a Beckett play. And that’s just how he likes it.


Now 34, Jake is five years into a remarkable run of movies, the equal of any actor of his generation. He was a force before – with Donnie Darko, Jarhead, Brokeback Mountain and Source Code – but there were blips too, like Prince of Persia, and The Day After Tomorrow. It was his 20s. “I took things because they were jobs,” he shrugs. “I mean people are paying you money, you’re 26 years old, are you kidding?”

Then something tectonic took place. His priorities shifted and his perspective changed. “I woke up one day and I wasn’t in the right room,” he says. “It was like a David Byrne song. That’s not my beautiful house. That’s not my beautiful wife.”

So he changed his life, the way men sometimes do around 30. He moved from his native Los Angeles to New York and pursued theater. He chose smaller budget independent movies, with darker, more challenging themes. He calls it “a growing up thing”. And a new Jake has emerged – still with the boyish features, the searching eyes and a wide smile, but older now, more determined. The frown furrows have deepened. The blips are history – every film he makes now is worth your attention. There are no blockbusters, action-adventures or cute love stories, not anymore. He makes films for grown ups. At a time when television is increasingly stealing the mantle from cinema in terms of sophisticated storytelling for adults, the Gyllenhaal brand is the antidote.

The change began with End of Watch, a heartbreaking story about two patrol cops in south east LA, an experience that he says “redefined for me how I wanted to make movies.” Next came Enemy, a haunting doppelganger thriller about split identity and madness from the French-Canadian director Denis Villeneueve. Jake so liked working with “Denee”, as he pronounces it, that before Enemy was even in the can, he committed to his second film, Prisoners, a bleak and gripping story of torture, child murder and obsession. Then late last year he produced and starred in Nightcrawler, a brilliant indictment of American society via the character of Lou Bloom, a sociopath and feral capitalist who rises from the grime of Los Angeles to become the head of a late night TV news service. How Gyllenhaal dodged an Oscar nomination for Nightcrawler is a mystery.

This year, the run continues, he’s on a roll. In reverse order, there’s Demolition this winter, a study in grief, alongside Chris Cooper and Naomi Watts – Jake plays a Wall Streeter who responds unusually to his wife’s death. Before that, in September, Everest tells the epic story of the 1996 climbing tragedy on which Jon Krakauer’s Into Thin Air was based – he plays Scott Fischer, one of the deceased climbers.

But first on the slate, this July, is Southpaw, a traditional boxing movie in many ways. He plays the fictional fighter Billy Hope, who is on top at first, then he loses it all, before fighting his way back, having been through a training montage featuring an Eminem soundtrack. The coach (Forest Whitaker) is a wise old boozer. It ticks the boxes. But underneath it all, is a story of shame, rage and redemption. Billy Hope’s anger earns him fortunes in the ring, until one day, outside of it, it costs him everything he cares about.

“He’s a guy that couldn’t deal with his own shame,” says Jake. “The director Ed Zwick [Love And Other Drugs] told me this wonderful thing: ‘Everything you learn is through shame.’ It’s so true. There’s those moments where you face a sense of humiliation, they’re so freeing if you can get through them.”

“What have you learned through shame?” I ask him.

He smiles. “I’ve learned a lot. But specific examples? I don’t know if I want to reveal all that.”

It’s a standout performance. As expected, Jake goes all out, on every front. His physique tells the story – he’s arguably the most chisel-ripped screen fighter in history. And he’s never less than convincing. Which is all the more impressive, given that Jake wasn’t even a fan of the sport before he took the job. “I didn’t do a boxing movie to do a boxing movie, if you know what I mean,” he says.

“Let me tell you about his commitment,” says Southpaw’s director Antoine Fuqua, who actually does train as a boxer. “When he first came to me, I said ‘have you ever boxed?’ and he said, ‘not really, just a bit of MMA stuff for End of Watch.’ So I sent him to see Terry Claybon, who trained Denzel [Washington] for Hurricane. And when Jake threw a punch, Terry said, ‘hell no! He can’t box!’ But now look at him. He can actually fight. That man trained like a beast.”

The regime was two 3-hr sessions a day, seven days a week for four months – a punishing schedule. And along the way, Fuqua would take him to gyms, to meet managers and promoters. “We saw the Pacquiao fight, we trained at Mayweather’s gym in Vegas,” he says. “Jake gave up whatever life he had to live the life of a fighter. And that’s an amazing sacrifice. He even broke up with his girlfriend because he was at the ring every day!”

The shoot was no cakewalk either. Jake was thrown into the ring on day one, where pros would pound him in the ribs and punch him on the jaw for the fight sequences, while a crowd of extras screamed at him from ringside. “I could tell he was hurting,” says Fuqua. “But we never used his stunt double. Jake did what a fighter would do – he went to the ropes and covered up. He was improvising fight sequences.”

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The truth is, he loves this stuff. The gym especially. Jake’s a cerebral type who loves to venture into abstraction and ideas – although today, it’s partly a way to avoid talking about his personal life (he’s fiercely private). But he also describes himself as “very physical”. He loves to transform himself for a role, whatever that requires. For Billy Hope he packed on the muscle, but for Nightcrawler, he dropped 30lbs. His character Lou Bloom is a ghoulish emaciated figure of the night, so he starved himself and ran 15 miles to set every day. It left him paradoxically both irritable and delighted.

“Physicality is a way into the mental state of a character,” he says. “I get off on knowing that my energy has shifted. My technical side is going, ‘yeah, you’re a bit of a maniac, but you know how to keep it in check.’ But it’s not like this huge deal. It’s that Louis CK thing, when people say they’re ‘starving’. Maybe you should rethink that word? You had a meal four hours ago!”

One of the things he enjoys about physical transformation is that it takes discipline, perhaps his favorite word. “Freedom is on the other side of discipline,” he says. “That’s a mantra of mine. Nothing comes easy if you’re going to do it well.” And that doesn’t just go for the physical aspect, but the whole process of preparing for a role. He hurls himself into it. “It’s what I love most about my job.”

He discovered this on End of Watch, when he and his co-star Michael Pena spent six months with LA cops and sheriffs, for a 22 day shoot. He’d never gone to such lengths before. They went on ridealongs to crime scenes, they heard bullets shoot past their ears, they saw dead people. “There were times, when I was taking cover, wearing a Kevlar vest and thinking, ‘come on, we’re making a movie!’ You know?” he says. But at the same time, he loved it so much, it changed his life. “I have never felt so good about being in Los Angeles, as when I was in East LA, working with police officers. Just being in that culture, especially the Hispanic culture. It was amazing.” To this day, one of his best friends is a former LA Sheriff.

Ever since then, he has approached every movie in the same spirit – total immersion. “It connects you to what’s really happening,” he says. “As an actor, it’s easy to become disconnected from reality, but I can also spend five months in an environment that most people would never get access to. So it’s actually a great way of engaging with the world. I’m not saying what I go through compares to what actual cops or boxers experience every day. There’s a hierarchy of importance, and actors are way down. I get that my job is absurd. I’m hyperaware of how ridiculous it is. But at the same time I take it extraordinarily seriously! Because as absurd as it is, it can also breed empathy.”

This is why he prepares so intensely. Because for Jake, empathy has a molecular, even mystical quality. “I believe deeply in the unconscious,” he says. “That you literally accumulate the molecules of the space that you’re in. We’re like 90% water, so naturally we are going to be affected by the moon when it’s full – if the sea is, why wouldn’t we be? That seems scientific to me. So if you spend enough time in whatever environment your character would exist in – the way I spent six months with police officers – then the molecules of that environment must transfer somehow. And then you put it on screen, and people go, ‘I feel something that I don’t normally feel.’”

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What this amounts to on shoot day is an actor who is zealous in his commitment. He puts everything into every scene. On Nightcrawler, the script didn’t require him to smash the mirror in a rage, but he did it anyway, and cut his hand open in the process. On Prisoners, he grabbed onto the back of Hugh Jackman’s truck as it pulled away and was dragged for a distance. That wasn’t written in either. It wasn’t even in frame. In Enemy, there’s a scene where Jake’s character is talking on the phone to his doppelganger, someone who looks exactly like him, and he’s not sure whether it’s real, or whether he’s losing his mind.

“We must have shot it 45 times,” says Denis Villeneuve. “I just kept the camera rolling and he was pacing around the room, doing it again and again like a mantra. He was trying to find something chaotic, to lose control. And afterwards, there was something so vulnerable in his eyes. His hands were shaking, he had gone so far away. For me, Jake is like a scuba diver – he goes deep, deep into the unconscious.”

This is partly Chris Cooper’s doing. When he co-starred with Jake in October Sky, back in 1997, the young actor asked the veteran for advice. “I told him, have no regrets when you leave a scene,” says Cooper. “Don’t leave anything on the table. This is a very competitive business, and for most people it’s short lived.”

Jake took it to heart. He swears by it. A case in point: the shoot for Everest last year. The director Baltasar Kormakur, a Herzogian figure, decided they would shoot in actually treacherous conditions – 4000m up the Dolomites of Italy, where it was -30 celsius. It was a scene in which Jake’s character dies of hypothermia, so he lay encased in the snow, essentially packed in ice. “I think he almost lost his hearing, that day,” says Kormakur. “His inner ear was frozen. His nostril hairs were frozen. And he wasn’t even getting that well paid!”

He describes Jake as “a bit of an oddball.” He’d hired him because he wanted a different energy in his cast. And Jake brought that in spades. “He’ll probably hate me for saying this, but he reminded me of Edward Norton’s character in Birdman. Brilliant when he’s acting, but weird in between, you know? He has a great sense of humor, but it’s not politically correct necessarily. Like he makes fun of people’s accents, and he can go off in that direction – it’s actually quite brave. But he gets away with it, because it’s always in a loving way.”

There were times, however, when Jake would push his fellow actors, and it didn’t always go over so well at first. “There were some hairy moments,” says Kormakur. “I thought – oh my God how’s this going to go? Because if Jake feels an actor’s not giving him what he needs, if he feels they’re not really there, he’ll say so. And sometimes, he even says afterwards, ‘sorry, I was an asshole.’ He’s aware of it, but would you rather be with a guy who’s always smiling and laughing, and never talks about anything serious, or your friend is a bit challenging, who isn’t afraid to argue with you. I prefer people with more width, you know? And this is part of his process. Acting is such a weird job, whatever you need to get there is fine with me. What Jake needs is to mess things up. Shake it up, dirty it up. It’s almost like he needs to get into trouble first before he can figure it out for himself.”

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The question I asked that rubbed him the wrong way wasn’t the one I thought might bother him – the one about going down on Naomi Watts in Demolition. Jean Marc Vallee, the director, another French-Canadian, laughed and told me, “ask him about that, it will be funny.” It wasn’t. Jake just calmly parried it in a professional manner. “I understand the curiosity but honestly, these questions, I find them so boring. Because whatever I say is not going to be respectful to the situation. And I don’t want to take the magic out of the thing you’re going to watch.”

The question that actually made him flinch was this: “Your childhood sounds magical, like it’s the Oscars in your kitchen every morning – was it?” Evidently, he has heard this characterization of his upbringing so often now that it grates. It makes him sound like Hollywood’s silver spoon son, to the manor born in show business terms. And on paper, that’s how it looks. Both his parents were in the industry – his mother Naomi, an Oscar-nominated screenwriter and producer, and his father Stephen, a director. As a result, the Gyllenhaal siblings, Jake and Maggie (two years older) grew up around this extraordinary Hollywood cast. Jamie Lee Curtis as a godmother, Paul Newman a family friend, who took him car racing at the age of 12. He met Sidney Lumet, Martha Plimpton and River Phoenix. And in the room above the garage lived a young Steven Soderbergh for a while, and after him, Ethan Hawke.

“I had a wonderful upbringing, don’t get me wrong,” he says, firmly. “But I don’t look at the world through rose-colored glasses. I wasn’t raised to be separate from reality.”

For example, they lived not in Beverly Hills but on the eastern flank of the city, where Koreatown meets Hancock Park – a sketchy part of town in the 80s. He may have attended the city’s most elite high school, Harvard-Westlake, but the Gyllenhaals weren’t loaded, not by LA standards. His dad would buy a house and fix it up himself. Work wasn’t always easy to come by. “I remember my parents made 2 or 3 things consecutively, but from then on out, it was just trying to get something made, and most of the time not succeeding.”

He was a wild teenager, “a mess” he says, but he was also a working actor, so his partying quickly gave way to the rigors of auditions and film sets. He made his first film aged 10, starring opposite Billy Crystal, and by the time he reached Columbia University, where he studied Tibetan Buddhism and eastern mysticism, he was so in demand that he had to drop out after two years.

Today, he looks back on those years with fondness. Because at university, at the age of 20, he was in his groove in life – doing theater, which he loves, and making films that chimed with the life he knew at the time. He was a confused teenager when he made Donnie Darko, the story of a confused teenager who hallucinates a figure in a bunny mask called Frank. But as the offers flooded in he increasingly made films that had less and less to do with who he was or what he cared about – “I was listening to other people, instead of myself.” And that’s how he ended up in the “wrong room” five years ago. Now he has returned to the groove of his Donnie Darko years, seeking out scripts that, as he says, “mimic a tone or timbre of where I am”. And he has at least a couple of people to thank for getting him back on track – his parents and Bruce Springsteen.

It was his parents’ divorce in 2009 that convinced him to move to New York. His dad remarried, and his mum moved to Manhattan, where sister Maggie had long lived with the actor Peter Sarsgaard and their two daughters. So Jake moved east to join the clan. And right away, it was easier to think straight. It felt good to escape his old life, the claustrophobia of show business in LA where “sometimes friendship and work gets intertwined in a confusing way.”

Chris Cooper suspects he was escaping celebrity culture. “I think Jake was being pecked to death by it,” he says. But Jake doesn’t see New York as much better than LA on that front. “It’s easy to say oh LA is that way and NY is that way, but let’s be honest. Especially today with all the cellphones. It’s more about just being away from Hollywood. Chris is someone I admire and he lives in Massachusetts. His life is separate from his work, and that’s something I want to cultivate too.”

His parents’ divorce also prompted the thought: “they’re following what they want to do, even though it’s difficult. So what do I want?” It wasn’t dissimilar to a question Bruce Springsteen asked himself when making Darkness on the Edge of Town, according to the documentary The Promise, which Jake watched at the recommendation of his publicist. It made a profound impact. “There was Steve van Zandt saying he could write 25 incredible pop songs, and they could have had five huge hit albums,” he says, “but Springsteen was like, ‘what do I want? I want to express something that comes from me, that feels like me.’ So I asked myself the same thing. Beyond money or fame or whatever, what do I like? And also who might want to work with me?”

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Here’s a picture of Jake in New York. He’s dancing in the streets of downtown Manhattan, really going for it, with his earphones in. And he’s getting some funny looks. Who’s that guy? What’s going on? Not everyone realizes it’s a scene in Demolition – the director Jean Marc Vallee is shooting him from a distance.

But it’s a fitting image for Jake – he’s happier out east. He lives up the street with his dog, a German Shepherd (name withheld). He pops in on his sister and mom on a regular basis. And he’s doing theater again, a big component of his new life. So far he’s done two plays, both by the English playwright Nick Payne. The most recent, Constellations, finished a four month run on Broadway in February.

“Sometimes actors do Broadway for cynical reasons,” says Payne. “There’s a perception in Hollywood that doing a play proves you’re a serious actor. But my impression is Jake genuinely loves it and he’ll do a play every couple of years.”

It’s true. There’s virtually nothing he doesn’t like about theater. It involves rehearsal, which is preparation, his favorite thing. He gets to walk to and from work every day, like a regular Joe – a clear separation between life and work. And lately, theater has allowed him to work with Brits, who are arguably his favorite nationality, even over Americans. “I guess I’m an Anglophile,” he says. “Pretty much all of my friends are Brits.”

It goes back to his 20s again, the Donnie Darko era. He was doing a play at the Garrick Theater in the West End – This is Our Youth – and he found the English to be particularly encouraging. “People told me, ‘you’re good at this, you should keep doing it.’ There was a sense of potential there,” he says. “You didn’t have to be the absolute best, but they could smell talent and they appreciated it, as long as you committed yourself.”

At the end of that run, Donnie Darko came out, and while it hadn’t been a flop in America exactly, it was far from a hit. But in England, a different story. “Street artists were doing art about it, it had this cult following. There was such a different response. British audiences were the first group who really understood me as an artist.”

It’s ironic, I tell him. Typically English actors come to the States for that sense of potential – they leave English pessimism for American optimism. And he laughs. “I don’t know. Maybe the English can sense my pessimism!”

Another English characteristic he has, is that he says, “flaunting things is embarrassing to me.” One of the things he noticed doing Constellations was that on Broadway, they’d get a standing ovation every night. And it made him uneasy.

“They never do that in the UK,” he says. “And that feels right to me. The standing O is like flaunting your applause!”

His English co-star, Ruth Wilson, can’t say enough good things about Jake. She got to know him very well over their run. Every night, they were the only two on stage, performing 65 scenes in 70 minutes, covering every possible permutation of a relationship between two people. After the show, they’d go out to dinner with friends. Jake invited her to his family’s Christmas Eve celebrations.

“He’s really generous,” she says. “He cares. Not just about the work, but about people. If I was ill, he’d provide me with pills and recommend a doctor. And he really brings you into his world. He was born into acting and show business – he knows everyone and everything about it. But he includes you. And I want to say, he’s a really great singer. We’d warm up every day, singing on stage and he like knows all the lyrics to Drake songs. And Motown and Springsteen. He knows the words to show tunes too. We went to dinner with my uncle, who puts on musicals at his Norfolk community center, and he and Jake were singing show tunes to each other in the middle of Balthazar. He really should do a musical.”

(And he is, as it happens. This summer, he’s doing The Little Shop of Horrors at the Lincoln Center in New York. Those ovations are going to keep coming.)

It wasn’t easy though, working with Jake. Easy isn’t his style. He pushed Wilson night after night. “Despite four weeks of previews, he kept demanding that we find the truth, and change stuff that felt old,” she says. “And we argued. We’d argue every week. We’d fight and then make-up and do the show and it was all fine. It was intense and intimate. We became like brother and sister.”

Jake acknowledges all this. He’s comfortable with confrontation, when it’s to do with the work. And it usually is. But today, he’s wondering about our interview. That’s the work at hand. The brunch crowd has left. They’ve had their bottomless mimosas and egg white scrambles. We’re the only two left, hungry and exhausted in the corner.

But Jake’s not done. He’s looking out the window, flipping his phone over idly on the table. “The thing is, you’re never going to get to know me in two hours,” he says. “If you want to do this properly, we need to spend two months. But we can keep talking. Is there something we’ve talked about that excites you, that you can write about? Maybe I can give you some more information…”