Acclaimed filmmaker Doug Liman knows firsthand that pushing boundaries and taking risks have helped him make good movies. He has the resume to prove it: Swingers, The Bourne Identity, Mr. & Mrs. Smith, Edge of Tomorrow, American Made. The list goes on.

His upcoming release out next year, Road House, is a remake of the 1989 classic about a muscle-bound bouncer, this time starring Jake Gyllenhaal. But you don’t have to talk to Liman for long before you realize that, for him, all roads, and the inspiration for many of his movies, lead back to home – in this case, a Chilmark farmhouse he purchased in 2006. Liman has been growing fruits and vegetables and raising goats and sheep there ever since.

Martha’s Vineyard Magazine caught up with the indefatigable director to talk about the weird way in which he asked Gyllenhaal to star in his latest movie, his not-so-secret farming aspirations, and why he turned his chicken coop into his top-secret documentary headquarters. An edited transcript of that conversation follows.

Martha’s Vineyard Magazine: You’re about to release a much-anticipated adaptation of the 1989 film Road House. Jake Gyllenhaal, who stars in the movie, also has Chilmark ties. Did you two meet on the Island?

Doug Liman: Jake and I became friends on Martha’s Vineyard, and in fact my version of Road House was born on Martha’s Vineyard because I saw Jake with his shirt off at the Chilmark Road Race. Iapproached him afterward and said, “I saw you with your shirt off. We should talk about remaking Road House together.” He said, “That’s a terrible idea, I’m in.”

In hindsight, you’re talking about an Academy actor. I’m not sure anyone had ever approached him in quite that way to do a movie…. But were it not for the Chilmark Road Race, there wouldn’t be a Road House. Which by the way, I’m so proud of. I think it’s my favorite movie I’ve made.

MVM: Recently, you auctioned off a dinner with you and Jake and a screening of that movie for the Possible Dreams fundraiser, to benefit Martha’s Vineyard Community Services. What can the winner expect?

DL: It will be a screening of a work in progress that they’ll see. The editing, the sound – we’re still finishing it. Jake isn’t really known for doing roles like the role he plays in Road House. But neither was Matt Damon [before he was cast in The Bourne Identity]. It’s part of what I’m so excited about for people to see. People get to see an actor they know so well in such a different light.

MVM: Speaking of dinner on the Island, you once told the Vineyard Gazette that, in the absence of bars and restaurants, dinner parties and talking to neighbors are the lifeblood of the Chilmark social scene. What would you describe as the ideal Chilmark dinner party? Who’s at the table and what would you serve?

DL: Well, what I would serve is easy because I have a pizza oven that I built during the pandemic that I’m very proud of. I’m proud of the pizzas it produces, along with other things I cook in it, like vegetables from the garden. As to who I would invite? I don’t know, I can’t answer that without insulting somebody. What I love about Martha’s Vineyard and the Chilmark social scene is how interesting the dinner conversations are with everyone who lives here. We may live on an Island, but everybody here seems to be thinking about the country and the planet in caring ways.

MVM: Let’s talk more about Chilmark. You gave an interview in Thomas Bena’s film One Big Home about the campaign to limit the size of houses in that town. You were also a staunch advocate against the causeway to the homes at Squibnocket Farm. Why are you so passionate about preserving the character of Chilmark?

DL: I’m from New York City, and before my family started coming to the Vineyard we used to go to the Hamptons. I witnessed firsthand a beautiful place being destroyed by misguided development. Thinking of the Vineyard becoming like the Hamptons, I don’t think it benefits anybody except maybe a high-end clothing retailer or a trendy, overpriced restaurant.

What’s extraordinary about Chilmark, and the Vineyard as a whole, is that people were thinking about conservation 100 years ago….The Hamptons was all potato farms, and nobody was thinking of conservation. Now the potatoes are all subdivisions and nothing but traffic jams. But on the Vineyard, the people who came before us – we’re talking about people who are long dead now, who were in charge 100 years ago – were thinking about how to preserve this place. We’re the lucky beneficiaries; we’ve inherited everything from them, and I feel an obligation to pass it on. Not only do I enjoy it myself, but I feel an obligation to pass to the next generation what we were so lucky to inherit. It’s fragile. I don’t know if we can pass a planet that’s not warming to our kids and grandkids, but I do know we can pass a Chilmark to them that resembles the Chilmark we know and love right now. That’s within our power.

MVM: You spend a lot of time tending to your farm animals, where you take on the alter ego “Farmer Doug” according to your Instagram. What does Farmer Doug get up to in the summers?

DL: Well, I have a couple of sheep and a beloved goat who’s been in the press.

MVM: You must be talking about Ruby?

DL: Yes, Ruby. She used to frequently escape and go down to Squibnocket Beach, because that’s where the people are. Then the cops would get her and put her in the back of the police car and drive her back to my house. They would complain that the police car then smelled like goat. But I also have tons of letters and emails from people who had chance encounters with Ruby on the beach who say it was one of the highlights of their summer….

My friends make fun of me. They say, “You’re just a gentleman farmer; you’re not a real farmer,” but I built a greenhouse just before the pandemic. I’m definitely a filmmaker who aspires to be a farmer. If you’ve ever tried raising animals or growing vegetables, you know it’s way harder than a trip to Morning Glory would make it look. I like a good challenge. I’m also incredibly impressed with the farmers on the Island and in Chilmark who make it work and who are net positive. But that’s part of preserving our way of life.

I should also say I’m not somebody who’s like, “Everything should stay the way it was.” That’s how you end up with Supreme Court decisions which are just living by rules that a bunch of racist, sexist white men came up with 200 years ago. I’m not somebody who is like, “Let’s live the way we used to live,” but there are some traditions that are worth preserving.

MVM: You mentioned the Supreme Court. Earlier this year, you debuted your first documentary, Justice, about Justice Brett Kavanaugh’s confirmation. The documentary was kept a secret until its screening. What can you tell us about that project?

DL: Did you know there’s a Vineyard connection on Justice as well? Not only was my chicken coop the top-secret headquarters for the film here on my property in Chilmark, but my interns were all people who lived on the Vineyard or summered on the Vineyard. My executive producers, Liz Garbus and Dan Cogan, just bought a house on the Vineyard. When I was deciding if and how I could make this film, every conversation I had was on Martha’s Vineyard. There is such a vibrant community of documentary filmmakers here....

MVM: It’s been almost three decades since your first feature, Swingers, debuted. What’s different now between the indie filmmaker who shot his own movies and the director you are today?

DL: I just had an extraordinary experience this spring where I shot a movie with Matt Damon called The Instigators. I did that after Road House, so I’m actually editing both of them now between New York City and Martha’s Vineyard....

It’s weird doing an interview, because I am reflecting, and I’m not normally a reflective person. I’m usually just thinking forward about new projects and new ideas; I don’t spend a lot of time dwelling in the past. But during the making of Instigators, I couldn’t help but be impressed by how much Matt Damon had grown. And, obviously, I thought he was extraordinary when we were making The Bourne Identity, so I didn’t know if there was room for growth, but he has become an even more extraordinary actor and human being.

When you’re with somebody who keeps impressing you from when you compare them to who they used to be, and they used to be great, I can’t help but be reflective of how I have changed myself. I think of myself as being an irreverent rule breaker when I made Swingers, and I remained that rule breaker when I made my first studio film, The Bourne Identity. So often I’ve thought of myself as not having changed and not having grown up, but … I’m committed to finding my own path and charting my own route and not copying other people – and, for that matter, myself.

I’m hoping that I’ve found ways to break the rules and still be respectful to the people around me that I maybe didn’t know how to do earlier in my career. I’ve found ways to break the rules but not necessarily break the relationships.

MVM: Your mother, Ellen Liman, is an artist who has been painting here for more than thirty-five years. Did growing up in an artistic household influence you?

DL: I grew up with a mother who was a photographer and a painter… and you would think because I’m in the arts, that it’s all the DNA that my mom passed to me or the lessons she taught me. But my father was a lawyer. As a filmmaker, I’m a storyteller. He, as a trial lawyer, would tell a jury a story, and then other side would tell the jury a story. So he, too, was a storyteller. I might have benefited from both my mother and my father being good role models for the skills and qualities that are important to make successful movies.

And, you know, my mom would kill me if we didn’t promote the fact that she has an extraordinary collection of oil paintings of Chilmark and of the whole Vineyard – she’s been painting Martha’s Vineyard since 1984. And she would also kill me for saying that, for anyone doing the math to figure out how old she is [laughs]....

MVM: Where can folks find you in 2024? Any new, non-secretive projects? 

DL: Well, only because you phrased it that way, they might find me in outer space with Tom Cruise. We are working on the project – not in secret, but we aren’t talking about it much. Tom just talked about it on the red carpet of Mission Impossible, though, so I’m not saying anything he hasn’t said in the last week. That project takes place in outer space, and what does that have to do with Martha’s Vineyard? Well, Tom came to see me here in Chilmark and I took him to the Menemsha Fish Market to pick up lobster, which we then cooked at my house. That’s where we first talked about shooting a movie in outer space –  in my outdoor dining room here in Chilmark. You can see why this place is so dear to me: all my creative inspiration comes from here; the people I respect most live here; the values I cherish most are embraced here.

MVM: And downtime? Are you running the Chilmark Road Race again?

DL: I’m definitely running the road race. I have made a lot of movies, but Road House is one of those movies that will be cherished forever, and it will forever be associated with the Chilmark Road Race. It would be wrong for me to say that I hope I can run the race with Jake, given that Jake runs about twice as fast as I do, but I love the community and the tradition….

I’m not a runner, by the way. I once went into the Adidas headquarters in New York to buy sneakers because the race was coming up. I walked in and they had thirty different running sneakers. I didn’t know there were so many choices; I just needed a pair of sneakers. So I get there and the salesman pulls out a clipboard with seven questions and I thought, “Oh my god, this is going to take forever. I just need running sneakers.”…

I said, “What are the questions?”

And he goes, “How often do you run?”

I said, “Once a year.”

And he said, “No, how often do you run? How often do you go running?” And I said, “Once a year. Once a year for the Chilmark Road Race.”

He looked at his questionnaire, and once a year wasn’t one of the options, so he just threw it away and grabbed a pair off the wall and was like, “How about these?” And I said, “Sold!”

I’ll always run the Chilmark Road Race. It’s great because if you’re lucky you might see some cows, and Krishana [Collins’s] flowers on the corner of Tea Lane.

MVM: And maybe even a ripped Jake Gyllenhaal with his shirt off?

DL: [Laughs] Yes, exactly. Hey, a bunch of movie stars are moving to the Vineyard; I might find my next casting at this year’s road race.