Stephen and Naomi — a couple of fugitives from the predictable middle class of the Northeastern United States — were doing relatively well. Stephen — born in a small town in Pennsylvania — was the oldest of six children. Naomi was the daughter of a pediatrician and a surgeon in NYC. They had gotten married and moved to LA in the 1970s, in search of an artistic life. He loved cinema, while she loved writing.

Stephen would end up directing made-for-TV movies, while Naomi would spend a few years as a production assistant on Sesame Street. They made a decent living, bought a house in Hancock Park — a residential neighborhood in the heart of LA — and had two children. They rubbed shoulders with Ted Danson and a young Steven Soderbergh. Paul Newman and Jamie Lee Curtis were their children’s godparents.

One day, at the age 11, the Gyllenhaal boy did something unexpected: he made Billy Crystal laugh.

The boy told jokes that were so absurd, yet he seemed to be totally serious. Crystal loved the young man’s intensity. He gave him a role in his next film — City Cowboys (1991) — and, with this, began one of the most long-lasting, varied and fascinating careers in recent cinema. This was Jake Gyllenhaal’s first step to becoming one of the last great stars of Hollywood.

Now, three decades later — at the age of 42 — he has half-a-dozen indisputable classics behind him, from Donnie Darko (2001) and Brokeback Mountain (2005) to Prisoners (2013) and Nightcrawler (2014). Now, after an Oscar nomination and a Tony nomination, his journey has arrived at one of its biggest turning points: his family’s living room.

This is where the actor — who has one of the most recognizable sad looks in the world — has recently managed to find a counterbalance to his workaholism and his propensity for intensity. And this counterbalance has changed everything. “If I had to describe this moment in my life, I would use the word ‘grateful,’” he explains. “I have a wonderful girlfriend [27-year-old French model Jeanne Cadieu], I feel close to my family and, over the years, I’ve seen my closest friendships deepen. I look forward to the future.” This is all new for him.

Gyllenhaal had his first leading role in October Sky (1999) when he was still in high school. It was difficult for him to return to the classroom: he felt light years away from his classmates after filming. His life became one shoot after another. His next project — Donnie Darko (2001) — was a legendary film about late-1990s melancholy, a classic for those who felt misunderstood. Gyllenhaal played a tormented teenager with schizophrenia, who served as an image of an alternative sex symbol. He was handsome, certainly… but nothing like the blonde arrogance of the captain of the football team. He disagrees, but it may be that Donnie Darko marked the rest of his life.

“What attracts me [to a role] as an actor is inexplicable, if I’m honest,” he reflects. “It has more to do with a confluence of things. The moment I’m in, what’s happening in my life, destiny. Usually, the connecting thread is the unconscious. I need to feel that there’s something beneath the story, a human theme.” In the 20 years that followed, he played thugs, ex-convicts, depraved people, obsessive artists and — on five occasions — widowers.

In 2002, he co-starred in Moonlight Mile, alongside Dustin Hoffman and Susan Sarandon. After filming, Hoffman said goodbye to him by giving him the book An Actor Prepares, by Konstantin Stanislavski, with the dedication: “You’re good, but you have to be better.” Gyllenhaal followed that advice. Perhaps because he was in demand for intense roles — or perhaps because he wanted to demonstrate that his capacity for work and his artistic ambitions went beyond those of any nepobaby — the actor threw himself into his projects with all of his body and soul, in an overwhelming way. He learned from some of the most intense method actors of his generation: Heath Ledger in Brokeback Mountain (2005) and Tobey MacGuire in Brothers (2009). In Nightcrawler (2014) he had to play a night owl outcast: for months, he ran 15 miles a day and chewed gum to skip meals. He lost more than 30 pounds for the role. His enormous eyes — protruding from his cadaverous face, like those of an insect — were “the most terrifying thing in the film,” according to The New Yorker.

Gyllenhaal then played a boxer with no future in Southpaw (2015): 2,000 sit-ups and six hours of training each day, becoming a ripped 178 pounds. “I can’t completely change the way I move or the way I look, but I can do the best I can with the support of artists who know what they’re doing,” he explains, when discussing his transformations. “I love using physicality — it’s one of the things I like to use the most in my work.”

We asked Gyllenhaal: “Why such ambiguous characters?”

“I like stories and characters that provoke conversations. I’m inspired by how complex it is to be human. I look for characters with whom to explore that complexity.

“Wouldn’t you prefer to play people more similar to you, create a brand, leverage your screen presence?”

“No matter how much experience you have — no matter how much acting technique you’ve developed — inevitably, your characters inhabit a reality different from yours. It’s also inevitable that the character sneaks into your life a little. But that’s why acting is a craft. It’s made up of a series of techniques and those techniques help you differentiate yourself from the character.”

“Aren’t you tempted, in such a polarized world, to play the hero and serve as an example?”

“The art of telling stories is, for me, inherently political. It’s important that we ask ourselves, as artists, what we want to say, what ideas seem important to us. Art — at its best — is capable of creating perspective and empathy. Those are the stories I want to tell.”

In 2008, Stephen and Naomi divorced. He stayed in Los Angeles; she returned to New York. Their eldest daughter, Maggie Gyllenhaal — who starred in Secretary (2002) and The Dark Knight (2008) — also moved back east, while Jake also went there shortly after. In the Big Apple, he found something difficult to receive when you’re an image projected on a screen: human warmth. He began to refine his technique to connect with the people around him. “I hope that the people I love love me back. I hope to earn their love by coming to their side, listening to them, being present for them. That’s what matters to me now,” he sums up.

He also started doing theater. In 2015, he debuted on Broadway in a play called Constellations. Years later, Maggie — who made her directorial debut with The Lost Daughter (2021) — would tell Esquire that she had never seen Jake so happy. He was relaxed — he really enjoyed the process. And he hasn’t forgotten it. “Theater is my first love, if I tell you the truth,” he tells EL PAÍS. “Making films is always an honor, I love making films. But I think theater allows another type of tension. In cinema, you need a plot to hook the audience. In the theater, one performance is enough to carry an entire work. There’s something incomparable to performing live in front of people. It’s a wonderful, exciting, scary and happy feeling!” he says.

This isn’t to say that Gyllenhaal has turned his back on Hollywood. In recent years, he has made movies for Marvel, director Michael Bay and Netflix. But he has always returned to Broadway, to New York, where he has dinner with his sister and his mother, where applause rains down on him for his enthusiasm. There, he has a playful, even childish energy. He’s even dared to do musical theater (Gyllenhaal has loved to sing ever since he saw La Bamba, the 1987 film about Ritchie Valens). “I love acting through songs. It’s a very specific skill,, but I think it’s how I communicate best as a performer. I’ve enjoyed musical theater since I was little, because it’s a space full of fun, but, more importantly, it’s the only genre in which a character’s intention can change from one second to the next. There can be four, five emotional shifts in a song. Something like this is only possible within a song.”

In 2017, he dared to take on one of the most complex protagonists in the genre: Georges Seurat in Sunday in the Park with George, composed by the legendary Stephen Sondheim. It was the last time he guided an actor through his devilish score before he died in 2021. “I remember him doing crossword puzzles before rehearsals began and during his breaks,” Gyllenhaal sighs. “It’s the image that remains of him: a gentleman fascinated by puzzles, sitting, patiently finishing The New York Times crossword puzzle. Working with him was a high point of my life and my career — it always will be,” he recalls. In 2019, he was nominated for a Tony for Sea Wall/A Life.

Nowadays, it’s hard for him to find the energy that, for years, he put towards being a movie star and proving his potential. But it’s also easy to detect a certain happiness about him — the happiness of a mature performer who allows himself to be atypical. It’s not common to confess that your favorite place in a bookstore is “the kitchen and design shelves.” Nor is it common for a leading man to lend his face to be the image of an Italian crockery line, such as Ginori 1735. “I’m interested in connecting with good people [who feel that] working hard means having a good time. Like the people at Ginori 1735, [a brand] that I’ve always loved. They make such beautiful things!”

And here we are: in a very different place from where we expected to end up. But it’s still a happy place. “In Sea Wall/A Life, director Carrie Cracknell encouraged us to interact with the audience, even if it was when a cellphone accidentally rang in the middle of the performance. The theater became a beautiful place of community with the public. I loved that detail and I take that feeling with me everywhere,” Gyllenhaal explains. “Let life inspire you, even if you’re acting,” he continues. “Prepare, prepare, prepare and then… forget about it and listen.” It sounds like that dedication from Hoffman — one that’s been improved over the years.

Things were going well for Stephen and Naomi. And now, they’re going well for Jake, too.

The October issue of ICON El Pais magazine is on newsstands now.

Gallery Links:
Magazine Scans > 2023 > Icon El País Magazine (Spain) | October
Photoshoots & Outtakes > Sessions > Photoshoots From 2023 > Session 001 [Icon El País]