His number 1 role was at age Fourteen within Over the Edge, which lead to roles in Little Darlings (1980) and Tex'' (1982). In the mid-1980s, Dillon experienced large roles in the Francis Ford Coppola's S.E Hinton adaptions The Outsiders (1983) and Rumble Fish (1983).

Witharound 1989, Dillon won critical acclamation for his performance when Bob in Gus Van Sant's Drugstore Cowboy.

Dillon continued to act withwithin early 90s by using roles in moving-picture show prefer Generation x picture show Singles (1992). He got somewhat of a career resurge when the role of Nicole Kidman's hubby inside To Die For (1995) and Wild Things (1998), and ''There's Something About Mary (1998) for which he received an MTV Movie Award for Best Villain.

Inside 2002, he too wrote & directed a 2002 film City of Ghosts, starring himself, James Caan and Gérard Depardieu.

His virtually all recent films come Crash, which was cowritten and directed by Paul Haggis, world health organization besides wrote Million Dollar Baby''. He besides stars within Disney's Herbie: Fully Loaded, playing bad boy racer Trip Murphy.

Selected Filmography
Herbie: Fully Loaded (2005) Crash (2005) ''There's Something About Mary (1998) Wild Things (1998) In & Out (1997) Beautiful Girls (1996) To Die For (1995) Singles (1992) A Kiss Before Dying (1991) Drugstore Cowboy (1989) The Flamingo Kid (1984) Rumble Fish (1983) The Outsiders (1983) Little Darlings (1980) Over the Edge (1979)