As a stage and screen actor, Jake Gyllenhaal is in the business of making realities from language. His personal theories on acting are like a re-spun version of the linguistic propositions in J. L. Austin’s 1962 book How to Do Things with Words. The British philosopher proposed that language didn’t merely communicate but enacted. A promise, a command, a warning, a declaration (“I now pronounce you man and wife!”)—such performative speech acts, Austin said, didn’t just describe the world but intervened in lived experience. Gyllenhaal, by interpreting the instructions of the script, transmutes the written word into an embodied text. “Acting is an interpretation of somebody else’s text,” he says. “So, if you’ve ever written an essay, it’s about writing an essay with your behavior.”

Movement talks in even his earliest adult roles: As Homer Hickam in biographical drama October Sky (1999), his shuffling gait conveys an earnestness as much as anything he says, and his tortured smirk is among the most memorable elements of his performance as the lead in Donnie Darko (2001). Gyllenhaal debuted, at the age of 11, in the Western City Slickers (1991), and in the more than three decades since, his career has spanned such varied roles as a dejected young adult in the West End production of Kenneth Lonergan’s play This Is Our Youth (2002), a closeted cowboy opposite Heath Ledger in Ang Lee’s romantic drama Brokeback Mountain (2005), and a deeply moral veteran-turned-police officer in David Ayer’s sleeper-hit cop thriller End of Watch (2012). Gyllenhaal is a true shapeshifter, with an inimitable attention to character detail, soon to be on display as he stars as Iago in the upcoming 2025 Kenny Leon-directed Broadway production of Othello, alongside Denzel Washington in the title role. As if these performances weren’t enough, last year he published a children’s book with Greta Caruso called The Secret Society of Aunts and Uncles.

Tank top by Tom Ford. Necklace and watch by Cartier.

Swiss art historian Hans Ulrich Obrist is likewise a master of linguistic performance. The artistic director of London’s Serpentine Galleries (where he’s worked since 2006), Obrist is perhaps best known for his unparalleled production of ultra-detailed artist interviews, inspired by those between Pierre Cabanne and Marcel Duchamp, which he read as a student. He began publishing these now-canonical conversations in Artforum in the ’90s, and later collected them in numerous books like his two-volume Interviews and The Infinite Conversations. His 2014 book Ways of Curating, something of an intellectual sensation, was built upon his decades of curatorial practice, legendarily launched by his 1991 The Kitchen Show, an art exhibition mounted in the kitchen of his apartment and featuring works by Peter Fischli and David Weiss. Right now, at the Serpentine, Obrist is spearheading the gallery’s “Year of AI” programming, a series of exhibitions and installations that merge art, architecture, performance, education, and human connection and situate them in our immediate technological future.

For Document, Gyllenhaal and Obrist offer a glimpse of their ongoing conversation about the many books, films, and people who inspire their work on the page, stage, screen, and beyond.

Shirt, tie, and belt by Tom Ford. Trousers and boots by Saint Laurent by Anthony Vaccarello. Watch and ring by Cartier.

Jake Gyllenhaal: The last time we spoke on Zoom, you had that same low-angle shot with all your books on your shelves behind you. The perspective makes it look like that dresser is about to fall on you.

Hans Ulrich Obrist: Yeah, and they’re still there, the books.

Jake: The perspective is pretty great.

Hans Ulrich: I once asked you what actors or actresses inspired you, and you said actually, the genesis of wanting to perform did not necessarily come from other performers. I wanted to revisit that question. Where’d the inspiration come from?

Jake: Frankly, for me inspiration can come from almost anywhere. Particularly, it’s at the beginning of the process, long before rehearsal even, when you have the text, or just the inkling of an idea and the relationship is between you and the text only. Your unconscious is allowed to wander, and then you can start to see that the world delivers things to you. I have a deep belief that the target draws forth the arrow. So, if I’m doing something, then there’s a reason. It’s not me who chose it. It chose me.

But to be more specific, I am constantly inspired by my sister and my brother-in-law. Paul Newman is, in terms of a performer, someone who always inspires me. Denzel Washington, too. I happen to have a very close friend in Jamie Lee Curtis, who inspires me as an artist as well as a human being. I tend to value one’s humanity over the art that’s created.

Hans Ulrich: And what is it about Paul Newman? You knew him during his lifetime.

Jake: I did. I happened to know him because my mother had written a screenplay for him and they became friends. I didn’t know who he was when I first met him—to me he was the guy who made salad dressing! I was very young, and in person he was just a nice guy. Then I started to work professionally, and I had the honor of being able to go to him if ever I needed advice.

Shirt, tie, and belt by Tom Ford. Trousers and boots by Saint Laurent by Anthony Vaccarello. Watch and ring by Cartier.

Hans Ulrich: I found this quote from him, which is beautiful. He said, ‘I’d like to be remembered as a guy who tried to be part of his times, tried to help people communicate with one another, tried to find some decency in his own life, tried to extend himself as a human being, someone who isn’t complacent, who doesn’t cop out. A man with no enemies is a man with no character.’

Jake: Amen to that. I think our imperfectness is what it’s all about, really. In Othello, for instance, the show I’m preparing for at the moment, there is the idea that Iago is one of the most evil characters ever written. But I can’t approach a character like that. There is no actionable stuff in that idea. He’s lonely, hurt. I’m on a search right now to understand the pain that he is in—per Paul’s quote. Where is the human in Iago?

“I’ve asked myself what would really frighten me as a performer, and Shakespeare was the answer.”

Left: Tank top by Tom Ford. Necklace by Cartier.
Right: Shirt, coat, and tie by Saint Laurent by Anthony Vaccarello.

Hans Ulrich: I was friends with Jeanne Moreau, and she always mentioned to me that one should never underestimate the importance of theater, of the stage. Even if somebody starts to do movies and is then famous for the movies, there is something very foundational about stage roles. What about the foundational aspect of stage roles, and then also, in addition to that, because it’s Othello, what appeals to you about taking on Shakespeare now?

Jake: Othello is profoundly prescient. As my old art history teacher from high school would say: It is meta-historical art, art that transcends time. It stays forever present. It is here to show us ourselves. It’s timeless. For me, there is a great challenge in performance, the challenge in interpretation. And I’ve asked myself what would really frighten me as a performer, and Shakespeare was the answer. I like—in a performance or on the stage—a deep challenge.

The word is king in the theater, but it is the essence and energy of a performer that carries the audience through the evening. I started in the theater; acting in front of people on stage was where I discovered I wanted to be a performer, so that has never changed. I’ve actually found it awkward to act in front of a camera. I mean, both are awkward to do, but I find it more awkward and harder to act in film than I do in the theater.

Hans Ulrich: And are there any roles in terms of your theater experience which you see as particularly foundational or transformational?

Jake: Absolutely. My first professional show, when I must have been 23 years old, I did This Is Our Youth, the premiere in the UK on the West End of Kenny Lonergan’s play. The humbling part of being in the theater is that you’ll be on stage with other actors, and it will feel so emotional for you—you’ll be crying at a scene, you’ll really feel connected—and then the director will come back after the show and say, ‘That was slow and boring and the audience was not moved. You were moved. Just do the simple task of speeding up your cues in the next show and see what happens?’ So, the next show, you speed it up, and you feel very little, but the director comes back that night weeping and says, ‘Oh, that was just incredible!’ There’s a powerlessness to the process. There’s a giving over to the expression in theater. It’s a deeply humbling process— you really are a vessel for the word.

The theater teaches you that the clarity with which you communicate, the simplicity with which you do it, is really powerful. And magic lies in moments where you let go: the moment where you hesitate, where you are unsure. And so to ask, ‘Why did I want to do Othello?’ It was to put myself in a position where I was unsure. I know that’s where really interesting things are created.

Coat by Saint Laurent by Anthony Vaccarello.

Hans Ulrich: There’s lots of parallel realities in your work because you work on many films. One project which we discussed last time is Road House. It’s a remake of the 1989 film, and we spoke quite at length about Patrick Swayze, and how you watched certain films of his 200 times. Can you talk a little bit about Patrick Swayze and the magic there, and then about what it means for you to remake Road House?

Jake: Patrick was a true artist. He was a dancer. He was a visual artist. At the same time, he made these really fun, action-packed, entertaining movies. I love that about Patrick. The first moment I met him, I felt connected to him because of that. Road House was great fun to do, and I admired him as a kid. I’ve watched Point Break [1991] maybe… I don’t know how many times I’ve watched that movie. I love it, and I love him in it. I continue to have great admiration for him.

Hans Ulrich: You told me that it’s really through Donnie Darko that you met, no?

Jake: Yes, we met on Donnie Darko. We basically shot the movie in a week and a half.

Hans Ulrich: This idea of watching a film again and again, that relates also to my field. I began my trajectory when I was a teenager. I met Gerhard Richter, one of the world’s greatest painters, and he was one of my mentors. With Gerhard Richter’s paintings, we can always look at them again and again. We can look at them hundreds of times. I’m very interested in you looking at certain movies that you cannot not watch every time they’re on. Why do you think that is?

“There are movies that we are just drawn to because we know structurally, behaviorally, and performance-wise, we will be held.”

Shirt, jacket, trousers, socks, shoes, and tie by Prada. Watch by Cartier.

Jake: There are movies that we are just drawn to because we know structurally, behaviorally, and performance-wise, we will be held. We know we are in confident hands of an expression that felt true to whoever’s doing it. There are other things that I just can’t not watch. When Magnolia [1999] comes on, the Paul Thomas Anderson film. Or Phantom Thread [2017]. And I think that is different from watching Point Break. But in the same way, there’s something in me—the engine in me, the little fire in my belly—that ignites. It’s that wonderful feeling of what Alan Watts would liken to meditation. There’s a blissfulness, so when you come back, you bring your history, but that little fire in you remains. It’s different than just being entertained or something. It’s deeper than that.

Hans Ulrich: That’s a great answer. You also said in an interview once that you love movies that are saying things that people might find odd at times.

Jake: I find that great artists will always show me the nooks and crannies of humanity that we might consider odd, but it’s those odd things that end up being the things I love: a specific odd character quirk. The oddity of who we are is what makes us us, I think. I guess ‘oddity’ might be the wrong word because that has a negative connotation, but it’s the distinctiveness of things, which is what I enjoy. I love people’s mannerisms and behaviors that make them unique. I was talking to someone the other day, and they do this same action over and over. I pointed it out, and they went, ‘Oh, do I do that?’ and I was like, ‘I love it. Don’t ever stop doing that.’ It’s an admiration for their uniqueness.

Hans Ulrich: I love that also with words, the strange use of words which one maybe doesn’t realize, or gestures. In my field, in contemporary art, there’ve been increasingly interesting collaborations between artists and fashion designers. My friend Philippe Parreno is now, for the third time, working with Nicolas Ghesquière for a very experimental stage for Louis Vuitton. Each time, it gets more interesting. And it’s a sculpture, it’s an installation. It’s, at the same time, a stage. It goes beyond the utilitarian. It produces reality where one plus one can be more than two.

You also have these longer-term collaborations with brands, and I’m interested to know a little bit more about the relationship with Cartier. Last time we spoke you mentioned that it all began with the Santos watch, and design and technology.

Left: Shirt, jacket, and tie by Prada. Watch by Cartier.
Right: Tank top by Tom Ford. Necklace by Cartier.

Jake: Yes, I cherish my relationship with Cartier. They have always been so supportive of me as an artist and it is a wonderful relationship. We share so much in our sensibilities and so when I wear their work—be it a watch or a necklace or a ring— it feels right. I have a friend who had collections of clocks. The construction of clocks, to me, is deeply fascinating; time itself and how we measure our lives. The Santos was the first wristwatch made for form but also practicality and function. It is so beautiful. My relationship with Cartier, my relationship with Prada, theirs are visions I share. To me, it works because I know that the choices I’ll make as an artist, I feel like they understand, they agree with, because that is a similar type of choice that they make in their work as a brand. Man, I feel honored to work with them.

Hans Ulrich: Can you talk more about your collaboration with Prada?

Jake: Mrs. Prada and Raf—I’ve known Raf for a long time now, and Mrs. Prada, I’ve obviously been a fan for many years. I have a real friendship with both of them. I love my conversations with Mrs. Prada. We talk about art, politics, film. She has such a fantastic sense of humor. Some people you just connect with so easily.

Hans Ulrich: Whenever I speak with Miuccia Prada, we talk about literature and philosophy, and that brings us to writing. I’m very interested in what appeals to you about writing. The tension between the way in which you’re supposed to practice writing, filmmaking, acting versus what works on a personal level, but also the idea of books, because you also make books.

The Secret Society of Aunts and Uncles is a children’s book which says that it is for aunts, uncles, nieces, and nephews only, and you are responsible for uncle-ology, and Greta [Caruso] is responsible for aunt-ology. It’s so amazing.

Jake: I wrote The Secret Society of Aunts and Uncles with my best friend Greta Caruso. Really, the book came together when we met our illustrator Dan Santat, who’s wonderful. He was so surprised at how few words I wanted on each page. I would say, ‘Oh, I’ll cut out those lines. Can you put that in illustration?’ And then, he’d draw it up real quick, almost as if we were looking at a scene playing out again. As if we were in the editing room on a film!

Before we started that book, Greta was not even an aunt and had no children. Now, she has two children and three nephews and nieces. She’s now responsible for mother-ology. I’m not the inventor of uncle-ology, I just coined the phrase. But that is a centuries-old art that I will not claim the invention of.

Hans Ulrich: Have you ever thought of writing a novel?

Jake: [Laughs] I do know I am not a novelist. But definitely a screenplay—and an essay is something I would really like to try and write.

Hans Ulrich: So that’s an unrealized project?

Jake: It is an unrealized project. By the way, I got the Sennett book [The Performer], and I started reading it just a little bit, so thank you for that.

Hans Ulrich: I’m so glad. When we talked about unrealized projects and books, you said, ‘I have a philosophy that actors and actresses are writing an essay with behavior.’ And that stayed with me throughout the week. It was very powerful, the idea of an essay with behavior. It’s so good.

Jake: People are maybe sometimes not sure about what acting is. A lot of times, people come to me and say, ‘Oh, you must be good at pretending or faking it or something.’ And I say, ‘That’s not what acting is at all.’ Acting is an interpretation of somebody else’s text. So, if you’ve ever written an essay, acting is writing an essay, but with your behavior. You need to have a great knowledge of the text that you’re interpreting, you need to do your homework, and eventually come up with your thesis. It takes, I think, a real intellect.

“The oddity of who we are is what makes us us, I think.”

Shirt and tie by Zegna. Coat by Dunhill. Ring and watch by Cartier.

Hans Ulrich: Of course, The Performer, the book by Sennett, is about the relations between performing in art, films, in politics, and then in everyday experience, and it looks at the physical, very bodily dimensions of performing modern worlds in a way. It also looks at rituals of ordinary life as being, in a way, performances, no?

Jake: Absolutely. When you watch a politician, they don’t point because they’ve been directed not to point. That is a performance; the behavior has been tailored. Watching the presidential debates: There’s been a lot of rehearsal, practice. There’s been the running of lines. They discussed: How does one stand? How does one greet the other? How does one look? What suit are they going to wear?

Your choice Hans, for instance, to have the camera be where it is. You may not see it as a choice. It’s at a low angle, and you see all your books in that angle. That is your choice, and this is your home. I love that your button is only half-buttoned right there in the center of your shirt. It’s buttoned, but not all the way. These are things that I would want to think about to make those choices for my character with a filmmaker.

Hans Ulrich: Another parallel reality of the many things you do is your production company, Nine Stories Productions, which you started almost 10 years ago in 2015. And you said that working with visionary storytellers and to bring other stories to life is what interests you most about that. Right now in contemporary art, in visual arts, a lot of the most interesting spaces are often artist-run spaces. And I think the same thing happens now in cinema where some of the most innovative spaces are invented by directors and by actors. I want to hear more from you about the importance of that in your practice.

Jake: Sometimes business can really overwhelm the art. The thing that’s very important about artist-run companies is that they allow for a protection to say, ‘Go with your instinct.’ We’re not necessarily always just trying to listen to the business. We’re trying to have you tell your story, and to be thought of and protected by other artists in your vision. When I’m in a group or in a scene with another actor, or where I feel that mutual understanding, I feel open to express in a deeper way. I wanted to create a space where we could help filmmakers and all different sorts.

I love cooking. I have many, many hundreds of cookbooks. I would love to be able to champion some young chefs and cooks who put their books out. I actually feel pretty well versed in the books of cooks [laughs]. I know that’s a strange corner, or maybe an odd corner that you wouldn’t expect for me to want to be involved in, but that’s definitely something I would love to do.

Shirt, coat, trousers, shoes, and tie by Saint Laurent by Anthony Vaccarello.

Hans Ulrich: My favorite cookbook is this one. Do you know this book? [Holds up his iPhone to show the cover of Synergetic Stew: Explorations in Dymaxion Dining]

Jake: Buckminster Fuller’s?

Hans Ulrich: Yes. It’s just been republished because it was really difficult to find. It’s basically Buckminster Fuller’s topic, the dymaxion idea, applied to food. On the occasion of his 125th anniversary, Lars Müller Publishers relaunched it.

Both you and I are friends of one of the greatest chefs, inventor of the River Café, Ruthie Rogers. You were also on her podcast. Maybe we should talk a little bit about her, because that’s somebody who inspires you, no?

Jake: Absolutely. She’s the one who always reminds me, whenever I float off, to go back to who I am, to what I really love. Outside of the beautiful food, the thing she’s the true master of is creating a community for people to enjoy themselves. It’s a living, breathing organism that you walk into when you walk into her space. A film is the same way, so I share a lot of that understanding in a different way. There’s nothing like a hug from Ruthie and a little bit of her spaghetti pomodoro. I don’t know anything better, honestly.

Hans Ulrich: I love that. I think that museum exhibition spaces can be living organisms. What’s your relationship to visual arts? What’s your favorite museum?

Jake: I have to say the Serpentine, that’s my favorite museum. There’s the broad scope of what we determine to be a museum. There are other museums beside the institutions. For instance, I think my grandfather’s home was a museum. The history of his life is a museum. I love living in New York for that reason. And when you say it’s a living, breathing organism, I love going to all of the museums in New York—the Neue Galerie, in particular. It’s not just being in the museum but walking up to the museum on the side of the park.

Shirt, jacket, trousers, and tie by Tom Ford. Watch and ring by Cartier.

Hans Ulrich: The idea of the museum of the grandfather is very interesting because I’ve just seen this show in Munich of Orhan Pamuk, the Turkish novelist. And he has this novel, The Museum of Innocence, which is related to the museum as something very personal.

Jake: Did that book win him the Nobel Prize?

Hans Ulrich: It’s a very exciting book. [Holds up his iPhone again to show the cover of The Museum of Innocence] I will text you the image. One last thing I wanted to ask you, which is a recurring question in my interviews, is advice. Rainer Maria Rilke wrote this beautiful book of advice to a young poet. And I always think it’s interesting for practitioners, artists in all disciplines, to give their advice to the new generation. What would be your advice in 2024 to a young aspiring actor or actress?

Jake: I would say be curious. Always try and stay curious!

Hans Ulrich: There’s another thing I thought was interesting. Chris Cooper once gave you advice, you said that he gave you the feeling that you walk into every scene, thinking, ‘Exhaust every possibility.’ Can you explain to me that Chris Cooper moment and why it was so important?

Jake: He said to me, ‘It’s an honor to do what we do, so you give it all of your mind.’ Particularly when you make a film, you have only so many takes, and then the experience is gone. So do as much work, dig as deep as you can, figure it out beforehand because, actually, the process is before the performance. The joy should be in the learning before you present. The real joy is in the research and the time, and that’s what I think he’s saying with ‘Exhaust every possibility.’ Oftentimes, if you show that vulnerability, the entire audience leans in. All anyone’s really looking for in the end, is the vulnerability of being human.

Grooming Kumi Craig at The Wall Group. Hairdresser Angela Soto. Set Design Gerard Santos at Lalaland Artists. Lighting Director Christian Larsen. Digital Technician Jennifer Czyborra. Photo Assistants Danielle Glovin, Muhammet Gencoglu. Stylist Assistants Devante Rollins, Rashied Black. Tailor Matthew Neff at Carol Ai Studio Tailors. Set Design Assistants Sasha Veryovka, Nick Sceau. Production Director Lisa Olsson Hjerpe at CHAPEL Productions. Production Assistant Jonny Berkowitz. Post Production She Post Production. Shot at WSA. Special thanks to Adrianna Varedi and Sam Wessner.