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

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

Matt Dillon, Eric Stoltz, Illeana Douglas, and John Turturro in Grace of My Heart (1996)

Matt Dillon and Kelly Lynch in Drugstore Cowboy (1989)

Liv Tyler, Matt Dillon, John Goodman, and Paul Reiser in One Night at McCool's (2001)

Uma Thurman, Matt Dillon, Lauren Holly, Timothy Hutton, Michael Rapaport, and Rosie O'Donnell in Beautiful Girls (1996)

Matt Dillon, Hayden Christensen, Paul Walker, Michael Ealy, Tip 'T.I.' Harris, and Chris Brown in Takers (2010)

Skeet Ulrich, Matt Dillon, Laurence Fishburne, Jean Reno, Milo Ventimiglia, Amaury Nolasco, and Columbus Short in Armored (2009)

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

Kate Beckinsale and Matt Dillon in Nothing But the Truth (2008)

Matt Dillon and Thandiwe Newton in Crash (2004)

Tommy Lee Jones, 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, 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)

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)