Matt Dillon Opens Up About 'Asteroid City,' His Breakthrough Moment and Working With Gene Hackman

Sorry to break the news, but Matt Dillon has bested you in making interesting and cultured summer plans.

Though he’s speaking from his Manhattan apartment on this late afternoon in May, he’s soon off to Europe. “My girlfriend [actress Roberta Mastromichele] is Italian and we spend half our time in Rome,” he says. The actor will also spend time in Paris playing Marlon Brando in Maria, a biopic about Last Tango in Paris actress Maria Schneider. He’ll listen to his beloved Cuban music. Plot out his next directorial project. Even paint a few works of art. “I do a lot of painting and most of my friends are artists and painters,” he explains. “It’s a place I like to go. I have to stay creative.”

Surprised? Don’t be. The New Rochelle, New York, native has been upending expectations for more than 40 years. A breakout star (and reluctant teen idol) in the ‘80s thanks to The Outsiders and The Flamingo Kid, he got serious in a hurry playing an addict in 1989’s searing Drugstore Cowboy. In the ‘90s, he became a reliable comedy star with hits such as Singles, In & Out and There’s Something About Mary. For his aughts output, he’s showed off his cerebral side: He wrote and directed the acclaimed 2002 drama City of Ghosts, delivered an Oscar-nominated performance in the highly charged drama Crash and popped up in 10 episodes of a small-screen thriller called Wayward Pines, among other indies and guest spots.

“The reality is that when you’re an actor, sometimes it comes down to the material and the job and the people you’re working with—but it’s often the material,” he says. “When the material is good, it’s a joy to come to work.”

He happily punched the clock on the set of his latest projects. In the Wes Anderson-directed Asteroid City (in theaters June 23), Dillon joined an A-list ensemble that included Tom Hanks, Steve Carell, Scarlett Johansson, Bryan Cranston and Edward Norton. The fanciful comedy, set in an American desert town during a space cadet convention in 1955, “is an allegory for post-COVID, post-quarantine times and a tip of the hat to classic American cinema,” he says. Back in the present day, Dillon plays a charming just-out-of-jail career criminal manipulating his ex (Patricia Arquette) for the Ben Stiller-produced Apple TV+ dark comedy series High Desert.

At age 59, Dillon tells Parade he’s grateful for both opportunities. “When you get older, you can handle characters that are more complex,” he says. “Patricia and I were saying that if we had worked together 20, 25 years ago, we would have been doing completely different kinds of roles. It’s a good time.”

But that doesn’t mean he can’t also thoughtfully look back on his accomplishments. He covers it all with Parade.

Mara Reinstein: Let’s start with Asteroid City. What’s it like acting with such a starry cast?

Matt Dillon: It was fun and a totally different experience. Everybody has a good attitude because of this world that Wes has created. You know, there are no extras. It’s actually a world within a world with everybody playing different parts. It’s funny when you see the movie, and there’s Tom Hanks in the background.

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And in High Desert, you’re finally joining the new streaming era of TV.

It’s more of a cinematic Hal Ashby comedy than a TV show. But I like that you’re not limited with structure. So many classic films have this basic three-act structure, but that’s not how it works in life. OK, there is a beginning and an end. But everything else is a conversation. There’s all kinds of stuff going on. There’s a lot of potential in that.

Going back to your own beginning, it’s pretty crazy that you were discovered while cutting class in junior high. 

I was just joking to Patricia that I didn’t have that “Mama, I want to sing!” moment. I didn’t come from a theatrical family. My father [Paul] was a painter. [His mom, Mary Ellen, was a homemaker.] My brother Kevin is an actor, but that’s not my background. I didn’t have an urge to perform.

Then why did you take that first role in [1979’s] Over the Edge? 

It was an interesting film. It was about kids in this town who seemed real and were very specific. It’s like you were turning the mirror to the audience. There was truth in it. I was only 14, but I recognized that and responded to that. I’m sure if that casting agent asked me to audition for some generic family movie, things would have been different.

Did you have the same reaction when you worked on The Outsiders? 

I remember reading the book, and it was so powerful. Here was this film about teenagers coping with life on their own terms. It’s like the code was cracked. Sometimes I go back to my old junior high school and the kids still ask me questions about the characters. They still have their own views. It turned out to be a classic book and a classic movie.

And, of course, it featured that classic cast. 

Yeah, it changed the trajectory of our careers. Well, not changed. It boosted us like a trampoline. Some of the guys were already established. Tom Cruise had already done Taps, and you could see where he was going.

Related: The Cast of The Outsiders: Where Are They Now?

You know, there really aren’t a lot of early duds on your resume. 

Awww, you are so kind. Of course, there are a few!

Can you name one regret? 

Well, I don’t focus on regrets. I did a movie called Target [in 1985], and to be honest, it’s pretty mediocre. But the reason I did it is because I wanted to work with Gene Hackman. He was a hero to me and is one of the greatest film actors ever. The movie was not a great experience but I learned a lot from him.

Do you feel like you had a breakthrough moment? 

It’s a business of ups and downs. Sometimes you don’t even know you’re down and you’re actually on the way up. I think Drugstore Cowboy was an important milestone for me. Everybody was like, “How can you make a movie about drugs?” Then you take a deep look at the personal story. When I wrote and directed City of Ghosts, it was probably the highlight of my life, personally. I wondered for years how I was going to get this thing made and do it in Cambodia. And then Crash won Best Picture [in 2006]. That was a great experience.

Crash was a pretty controversial Oscar Best Picture winner at the time. What do you make of the movie now? 

Obviously, it’s still relevant. A lot of things in that movie are much more in the forefront of the conversation now. And you know not a lot of people were interested when we made it. But there was a payoff. Sometimes when you take risks in film, it can be rewarding. You can have such freedom, and yet there’s so much fear in this business. That’s why it’s so tough.

Did you think There’s Something About Mary was a risk? Especially when you’re giving CPR to a stuffed dog. 

That’s just fun. When you show that you’re having fun, it transmits to the screen. And [writer-directors] Bobby and Peter Farrelly really pushed the envelope and put it out there. I had dinner with [co-star] Ben [Stiller] last night, and we started laughing about the things we remembered from filming it. We quoted one of the lines that my character said to Ben.

You’ve excelled in quite a few memorable comedy roles. Are you a funny guy? 

I mean, when you’re an actor that doesn’t have a comedy background, there’s less pressure. And yet, you know, there’s something about comedy that’s serious. It’s a real commitment from the actors. And the best comedy has truth that we can identify with. We identify with the time, place, people and story.

You were also in the Madonna video “Bad Girl” and shared a screen with Pearl Jam and Soundgarden in Singles in the early '90s. Any standout memories? 

So, there were all these talented bands in Seattle during that time, and it was a scene. But I’m from New York. I didn’t really know them. I didn’t know Nirvana. I remember [writer-director] Cameron Crowe was like, “You gotta meet these guys!” and it was Pearl Jam. Eddie Vedder had just joined the band. They hadn’t quite broken yet but you knew they were going to be big.

So, are you a big music guy in general? Share a little bit about your life. 

I love Cuban music, and I’ve been into it for a long time. I directed a movie called El Gran Fellove about a Cuban scat singer named Francisco Fellove as he was making his last record. I actually began filming it in 1999, and I’m so proud of it. I don’t usually read reviews because nobody wants to read something negative, but this was different. That’s finally your vision up there on the screen.

Do you ever just hang on the couch and watch TV? 

I do! I like to watch stuff! But I’m negligent and not up to date. I haven’t watched Ben’s show, Severance, and I hear it’s great. I’ve got a real soft spot for documentaries too. I think it’s a misunderstood medium.

You don’t do social media. You’ve never been in a superhero movie. You just don’t seem like an actor chasing that brand of stardom. Is that accurate? 

Well, thank you for saying that. I appreciate that because I don’t know how else to do it. I only know how to be true to myself. I mean, there are times when I wish I were more ambitious about this or that. But you have to follow your own path. That’s what I aspire to do.

It definitely seems like fans don’t associate you with, say, Herbie: Fully Loaded. 

Exactly! Well, you’ve still got to work and take care of yourself. But I’ve learned that I’m only as good as the filmmakers I’m working with, and the scripts. I don’t believe I am good enough to overcome something that’s not good. And I’m at the point now where people look to me as someone with experience, so they listen to what I have to say. I’m been doing this for a long time and can learn from my successes and mistakes.

Asteroid City is screening now in theaters. 

Next, Everything To Know About 'Asteroid City,' Including Cast, Release Date and More