ESQUIRE: The Cartier Santos timepiece is named after Brazilian aviator Alberto Santos-Dumont, who famously said: “Even in the worst of times, you must never give in to discouragement, but instead use your failure to start again.” How do you relate to this quote as an actor?
JAKE GYLLENHAAL: There is this wonderful quote that basically says: “We learn from our failures more than we learn from our achievements or triumphs. And, if that’s so, why don’t we learn about the people who failed?” I sort of love that idea on why don’t we hold up to people who came in second place. I believe that deeply. Failures are some of the most beautiful times to look back on because they inform the changes and decisions you make to move forward. That sense of birth comes right out of that time. So I think you have to be hopeful, have a vision, see where you want to go and believe in it. Trust your instinct. You can’t constantly be trying to look for failure. That’s not a good thing. But when you don’t succeed, that’s when the lesson comes.
ESQ: You have a knack for playing extreme characters, but presenting them in an honest way. Why are you drawn to characters like Lou Bloom in Nightcrawler, Morf Vandewalt in Velvet Buzzsaw and Mysterio in Spider-Man: Far From Home?
JG: I have a desire to understand why people are the way they are. So often, my own judgement of someone in the past has led me away from discovery. More and more, I discover that if I begin with judgement, I become curious about it. And every time I move into that idea, it makes me realise something about myself.
ESQ: Spider-Man: Far From Home is your first foray into the Marvel Comic Universe and playing an action hero. Was your experience what you expected it to be? Did you think the decision to take on this role was risky or were you like ‘let’s do this’?
JG: I was excited about it. But it was risky because I used to think I couldn’t ever create a character in this type of world. I was surprised to discover that I could. Also just the size of the movie. The process of it. You jump in and everyone is like ‘go’. You’re just expected to deliver.
ESQ: And the fans in the universe are extreme…
JG: They are! They are also amazing. We were in Brazil a couple of months ago for Comic-Con and the response was just overwhelming. You just go like ‘oh my god’. This is huge.
ESQ: What was it like working with Tom Holland? Judging from your social media, you seem to have a good camaraderie with him.
JG: I adore him. He’s a good man and he’s someone who’s been raised well. He’s a good person and polite, but loves to have fun. He’s not too straight-laced. He’s just a great guy and I also love that we are from two different generations. He also has real admiration for people who are older than him and have more experience, even though he has had so much success at such a young age.
ESQ: You just finished an off-Broadway play, Sea Wall / A Life. Do you find that there’s a big difference between theatre and film?
JG: I do. I feel more at home on stage than in front of the camera. It just feels like there’s a bigger space to play. To me, it’s where I hone bolder choices. In the confines of a film, I feel that your choices become small sometimes; not as courageous. But when I go on stage, your choices are tested live in front of a group of people. There are mistakes to be made, but those mistakes become an exploration.
ESQ: Sea Wall / A Life talked about fatherhood. In your opinion, what does it mean to be a man today? Do you think there are enough stories in the entertainment sphere that discuss the modern issues facing men?
JG: In the world that I work in we’re still struggling with the clichéd idea that masculinity is tied to strength. And if I’m being honest, I’ve never really fitted in, I’m not too sure about my space in my own industry. I’ve tried to find my own sense of belonging, like: ‘Oh, I fit in here and this is the way I’m supposed to be’. But over time, I released I just didn’t fit into the norm. There’s a big part of me that can fit into the industry, but that’s also a big part of me that’s odd and likes obscure things.
ESQ: You can see that with the choices you’ve made; in terms of the characters you’ve chosen to play.
JG: Yeah. I love Spider-Man the movie. But then, I also love making movies like Donnie Darko and some people question why I make such dark choices. But it doesn’t feel dark to me. It may have dark elements, but it’s also fun. I think I’ve searched for what it means to be a man through the roles that I’ve played.
ESQ: So what have you discovered about what it means to be a man through your work?
JG: I think it is a balance of masculine and feminine traits. And embracing what you love. For instance, I’ve learned that about fashion. When I was a kid, I was making bolder choices. You see kids dressed in weird clashing fabrics in weird bright colours and carrying crazy backpacks. People go like, ‘that’s just a kid’. But sometimes people wake up and figure that, ‘Hey, this is what I love. I’m going to carry that weird backpack again and wear those shoes. Because I love them and they bring me joy.’ To me, that is what being a man is. Embracing the stuff that you love and what brings you joy.
ESQ: Talking about fashion, as an ambassador for a brand like Cartier, do you feel pressure to be on point style-wise? Because you’re in the public eye a lot, are you conscious of what you’re wearing?
JG: I’m conscious of being thoughtful and being dressed appropriately for the room that I’m walking into, but beyond that, not really. I think if people are going to judge, they will judge no matter what I wear. But I do like being put together. Dressing up for special events makes me feel confident; it’s like wearing armour.
ESQ: You recently joined social media. Why did you decide to take the plunge?
JG: I still haven’t really decided to jump right in. [Laughs]. I only have one foot in it now. Social media feels dishonest somehow as a medium. As with almost every medium, including movies, it is hard to be honest.
ESQ: Do you reveal more about yourself in theatre or in film? Is it true that theatre requires bigger gestures whilst film is all about the smaller movements?
JG: I have a different philosophy. A performance in film has been created by a large group of people, not just the actor. The beautiful thing about theatre is that the work is who you are and what you do; what you stand for as an actor is very clear. I don’t believe in big acting on stage. In Sea Wall / A Life, Tom Sturridge and I try as much as we can to speak as if we were speaking and feel as if we were feeling. To be present in the moment. It is a presentation and not a representation.
ESQ: What is more important: a good script or a good director?
JG: A good director. I say that only because there are great and bad movies made from equally good scripts. I think you need a great director to interpret a good script and, sometimes, a bad script can be saved through good direction. Ultimately, film is a director’s medium