One of his next roles was in Liar's Moon, where he played Jack Duncan, a poor Texas boy madly in love with a rich banker's daughter. In the early 1980s, Dillon also had prominent roles in three adaptations of S. Hinton novels: Tex (1982), The Outsiders (1983) and Rumble Fish (1983). All three films were shot in Tulsa, Oklahoma, Hinton's hometown. The Outsiders and Rumble Fish had Dillon working with Francis Ford Coppola and Diane Lane.
He followed those up with The Flamingo Kid in 1984. He made his Broadway debut with the play The Boys of Winter in 1985. Dillon did voiceover work in the 1987 documentary film Dear America: Letters Home from Vietnam. In 1985, Dillon was namechecked in the lyrics of the Roger Daltrey song 'After The Fire' (written by Pete Townshend).
In 1989, Dillon won critical acclaim for his performance as a drug addict in Gus Van Sant's Drugstore Cowboy.ĭillon continued to work in the early 1990s with roles in films like Singles (1992).
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He had a resurgence when he played Nicole Kidman's husband in To Die For (1995), as well as starring roles in Wild Things (1998) and There's Something About Mary (1998), for which he received an MTV Movie Award for Best Villain. In 2002, he wrote and directed the film City of Ghosts, starring himself, James Caan and Gérard Depardieu. In 2005, he starred in Factotum, a film adaptation of an autobiographical work by Charles Bukowski.