Nicole Kidman and Matt Dillon in To Die For (1995)

Francis Ford Coppola, Matt Dillon, and Buddy Joe Hooker in The Outsiders (1983)

Francis Ford Coppola, Matt Dillon, and Dennis Hopper in Rumble Fish (1983)

Michael Douglas, Matt Dillon, Anthony Russo, and Joe Russo in You, Me and Dupree (2006)

Matt Dillon, Bobby Farrelly, and Peter Farrelly in There's Something About Mary (1998)

Matt Dillon at an event for Being Maria (2024)

Patricia Arquette, Matt Dillon, and Bernadette Peters at an event for High Desert (2023)

Matt Dillon at an event for Land of Dreams (2021)

Patricia Arquette and Matt Dillon in High Desert (2023)

Matt Dillon and Tom Hardy in Capone (2020)

Mira Sorvino and Matt Dillon in Beautiful Girls (1996)

Matt Dillon and Timothy Hutton in Beautiful Girls (1996)

Matt Dillon and Ilona Grübel in Target (1985)

Matt Dillon and Dean R. Miller in My Bodyguard (1980)

Matt Dillon, C. Thomas Howell, and Ralph Macchio in The Outsiders (1983)

Matt Dillon and Emilio Estevez in The Outsiders (1983)

Matt Dillon and C. Thomas Howell in The Outsiders (1983)

Kim Cattrall, Matt Dillon, and Andrew McCarthy in Mannequin (1987)

Matt Dillon, Emilio Estevez, and Meg Tilly in Tex (1982)

Tommy Lee Jones, Diane Lane, and Matt Dillon in The Big Town (1987)

Matt Dillon and Sean Young in A Kiss Before Dying (1991)

Matt Dillon, Christina Applegate, and Steve Zahn in Employee of the Month (2004)

Matt Dillon, Vincent Spano, Pamela Ludwig, and Harry Northup in Over the Edge (1979)

Sandra Bullock, Don Cheadle, Matt Dillon, Brendan Fraser, Ludacris, Thandiwe Newton, and Michael Peña in Crash (2004)

Matt Dillon, Kate Hudson, and Owen Wilson in You, Me and Dupree (2006)

Matt Dillon, Lili Taylor, and Marisa Tomei in Factotum (2005)