Matt Dillon: What happened to Matt Dillon and what is he doing now? | Explainer

Matt Dillon was undeniably one of the biggest stars of the 1980s and ’90s, with a string of blockbuster films to his credit.

Starting out as a teen heart-throb in films such as The Flamingo Kid, Dillon’s most famous early role was in The Outsiders, before he reinvented himself as a comedy actor in There’s Something About Mary alongside Cameron Diaz, whom he dated.

Now 60, Dillon, who won a new legion of new fans after guest starring in the sitcom Modern Family, is again enjoying a career resurgence.

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Matt Dillon was born in New York state on February 18, 1964, to stay-at-home mother Mary Ellen and Paul Dillon, who was a former college golf coach among other jobs.

He was one of six children, including younger brother Kevin Dillon, also an actor, who grew up in Mamaroneck, about 33km from New York City.

Dillon was skipping class when he was discovered and asked to audition for a new film. He won a part in Over the Edge, which was released in 1979, when he was just 14.

In a 2023 interview with Parade, Dillon said there was no doubt his first role shaped his career.

“I’m sure if that casting agent asked me to audition for some generic family movie, things would have been different,” he said.

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From there he appeared in teen movies Little Darlings, starring Tatum O’Neal, and My Bodyguard, both of which were box office successes on their release.

But it was his part as Ponyboy in the 1983 Francis Ford Coppola-directed drama The Outsiders that cemented his place as a star and remains one of his most iconic roles 41 years after its release.

Dillon told Parade last year the film was still finding new audiences.

“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,” he said.

Dillon went on to star in another Francis Ford Coppola film Rumble Fish, straight afterwards.

Like The Outsiders, it was based on a book by S.E Hinton, with whom Dillon remains close decades later.

Critically acclaimed roles followed, such as a drug addict in the 1989 film Drugstore Cowboy.

He played Nicole Kidman’s hapless husband Larry in another Gus Van Sant film, 1995’s To Die For, then starred in the 1998 hit film Wild Things.

That year he starred as private investigator Pat Healy in the romantic comedy There’s Something About Mary, which won him the MTV Movie Award for Best Villain.

The Outsiders cast: Then and now

His co-star in the film was his then real-life girlfriend Cameron Diaz.

The couple reportedly started dating in January 1996, but kept their relationship largely out of the spotlight.

Diaz told The Guardian in 1997, “I love him incredibly,” and once told Rolling Stone, “Matty, he’s the best. He’s one of a kind.

“He’s never taken that commercial route. He’s an intelligent, poetic, full, real human being. And he’s down-to-earth. Matt is the greatest.”

The couple broke up in 1998 after dating for two years. Dillon, who was eight years older, later told Rolling Stone the relationship “ran its course.”

“Look, I loved her and we were very close, but it just ran its course. We’re both actors; she was living in LA and I was living in New York, and I didn’t want to commit to moving out there,” he said.

“But I don’t want to say it was about any of those things. It just ran its course.”

He told Parade in 2006 their relationship was a first for him.

“I fell in love. It’s a very powerful thing when you feel that way about somebody. Cameron was a muse for me. I hadn’t been in any deep emotional relationships.”

He is still close to another There’s Something About Mary co-star Ben Stiller, telling Parade last year, “I had dinner with Ben 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.”

Dillon made his directing debut in 2002 for the film City of Ghosts, which he also wrote.

The 2000s saw him appear in the comedy, You, Me and Dupree, as well as drama Crash, which earned him the Independent Spirit Award, and Golden Globe and Academy Award nominations for Best Supporting Actor.

He starred in the 2018 thriller The House That Jack Built and last year’s Asteroid City.

Most recently he played Marlon Brando in the biopic Being Maria, which premiered at this year’s Cannes Film Festival, which Dillon attended.

Despite being a movie star, Dillon has embraced TV in recent years. As well as a guest appearance as Claire Dunphy’s teenage boyfriend Robbie in Modern Family, he starred in the drama series Wayward Pines and last year’s comedy series High Desert.

He told Parade last year there was no doubt his roles had become more varied.

“When you get older, you can handle characters that are more complex,” he said.

“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.

“When the material is good, it’s a joy to come to work.”

During the same interview, he looked back on his career.

Iconic Hollywood couples from the ’80s

“I think Drugstore Cowboy was an important milestone for me,” he said. Everybody was like, ‘How can you make a movie about drugs?’

“When I wrote and directed City of Ghosts, it was probably the highlight of my life, personally. And then Crash won Best Picture. That was a great experience.”

Dillon was in a long-term relationship with Italian actress Roberta Mastromichele from 2014 to 2023.

Dillon has a net worth of about $60 million. He has never married or had children, and lives in Manhattan.