Skipping class is usually a bad plan. You get caught, you get detention, and that's the end of it. For one Mamaroneck kid in the late '70s, it went a little differently. It turned Matt Dillon into a movie star.
Scouts Found Him in the Hommocks Hallway
Dillon grew up in Mamaroneck. Hommocks is the Mamaroneck school district's middle school, on Hommocks Road. It has a Larchmont mailing address, so some people call it a Larchmont school.
A movie crew came through Westchester looking for kids for a film called "Over the Edge." They didn't want polished child actors. They wanted kids who looked like real kids. So they went to his school, and they spotted Dillon in the hall. He was supposed to be in class.
He didn't even want to audition, he told Cigar Aficionado in 1996. He went anyway. "For some reason, I knew I was going to get the job," he said.
He got it. He was 14. "Over the Edge" came out in 1979, and it was his first movie. A year later he was in two more, "Little Darlings" and "My Bodyguard."
The Mamaroneck Historical Society still tells the hallway story. It comes from Dillon's own 1980 interview with the Daily Times, his hometown paper.
Then Coppola Cast Him in The Outsiders
"The Outsiders" came out in 1983. Francis Ford Coppola directed it, and it was based on S.E. Hinton's 1967 novel. Dillon played Dallas "Dally" Winston.
The cast was stacked. Tom Cruise, Patrick Swayze and Rob Lowe are on the slide. Ralph Macchio was in it too. So was Emilio Estevez. C. Thomas Howell and Diane Lane rounded it out.
Dillon already knew Hinton's world. In 1982 he starred in "Tex," another movie made from one of her books. Hinton has said "Tex" is how she met him. Then Coppola cast him again in "Rumble Fish," one more Hinton story, also out in 1983. That's three Hinton movies in two years.
The house on the slide is the Curtis brothers' house from the movie, in Tulsa. The rapper Danny Boy O'Connor bought it in 2016 and fixed it up. It opened as The Outsiders House Museum on Aug. 9, 2019. The photo is from 2017, before the museum opened.
Then Little Brother Kevin Followed Him
Kevin Dillon is about a year and a half younger than Matt. He grew up in Mamaroneck too, and he graduated from Mamaroneck High.
In 1986 he was in "Platoon." That movie won Best Picture.
Then came the role most people know him for. He played Johnny "Drama" Chase on HBO's "Entourage" from 2004 to 2011. The part earned him three Emmy nominations, in 2007, 2008 and 2009. He played Drama one more time in the 2015 "Entourage" movie.
And That Hallway Kid Got Oscar-Nominated
Matt kept working. Then came "Crash," and it earned him an Oscar nomination for Best Supporting Actor. At the Academy Awards on March 5, 2006, "Crash" won Best Picture.
He didn't leave that awards season empty-handed. The night before the Oscars, he won the Independent Spirit Award for Best Supporting Male, for the same role.
So each Dillon brother has a Best Picture winner on his résumé. Kevin has "Platoon." Matt has "Crash." And both of them started out in Mamaroneck.
It all goes back to a 14-year-old standing in a Hommocks hallway when he was supposed to be somewhere else. We're not saying skip class. We're just saying it worked out for him.
Did you go to Hommocks or Mamaroneck High? Who's the most famous person who ever walked your school's halls? Tell us on Instagram at @the914collective. And for more Westchester stories, subscribe to the free Not Upstate digital magazine at thenineonefour.com.
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