Matt Dillon and Janet Jones in The Flamingo Kid (1984)

Matt Dillon and Suzy Amis in The Big Town (1987)

Matt Dillon and Cindy Fisher in Liar's Moon (1981)

Matt Dillon in Herbie: Fully Loaded (2005)

Matt Dillon and Herbie in Herbie: Fully Loaded (2005)

Matt Dillon, Thomas Lennon, and Jimmi Simpson in Herbie: Fully Loaded (2005)

Matt Dillon and Lindsay Lohan in Herbie: Fully Loaded (2005)

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

Tom Cruise, Matt Dillon, Emilio Estevez, Rob Lowe, Patrick Swayze, C. Thomas Howell, and Ralph Macchio in The Outsiders (1983)

Diane Lane and Matt Dillon in Rumble Fish (1983)

Diane Lane and Matt Dillon in The Big Town (1987)

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 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)