At age 14, was spotted by casting director Vic Ramos while cutting class in junior high school
Made Broadway debut in "The Boys of Winter"
Made feature directorial debut with "City of Ghosts"; also co-starred
Made TV debut in "American Playhouse" (PBS) production of "The Great American Fourth of July and Other Disasters"
Played a hunk who deflowers Kristy McNichol in the camp drama "Little Darlings"
Played a racist cop in Paul Haggis' directorial debut, "Crash"; earned Oscar, Golden Globe and SAG nominations for Best Supporting Actor
Portrayed the troubled teen leader of "The Outsiders," based on the S.E. Hinton novel of the same name; first film with Francis Ford Coppola and Diane Lane
Cast in the Disney feature "Herbie: Fully Loaded" with Lindsay Lohan and Michael Keaton
Co-starred with Kate Beckinsale in Rod Lurie's "Nothing but the Truth"
Played a popular guidance counselor accused of raping two students (Neve Campbell and Denise Richards) in the campy thriller "Wild Things"
Played a schizophrenic homeless man in "The Saint of Fort Washington"
Played titular character in "Tex"; first of three alienated teens Dillon portrayed in films based on S.E. Hinton novel
Starred as Nicole Kidman's doomed husband in Van Sant's black comedy "To Die For"
Cast as the bully in "My Bodyguard"
Co-starred with Kyra Sedgwick in the Kevin Bacon directed "Loverboy"; premiered at Sundance (lensed 2003)
Directed an episode of the HBO drama "Oz"
Grew up in Mamaroneck, New York
Played an alienated teen living in his brother's shadow in Coppola's "Rumble Fish"; again co-starred with Lane in another film based on a Hinton book
Featured as a sleazy private detective hired by Ben Stiller to track down Cameron Diaz (then his real-life girlfriend) in the Farrelly brothers comedy "There's Something About Mary"
Had featured role in the independent film "Deuce's Wild"
Made film debut in the violent teen drama "Over the Edge"
Played a dim-witted Seattle grunge rocker in Cameron Crowe's ensemble comedy, "Singles"
Played a newlywed married to Kate Hudson in the comedy "You, Me and Dupree"
Played a non-hoodlum role in Garry Marshall's "The Flamingo Kid"
Played an actor who outs his high-school English teacher (Kevin Kline) during his Oscar speech in the comedy "In & Out"
Won rave reviews for his portrayal of a junkie who robs drugstores to support his habit in the critically acclaimed "Drugstore Cowboy"; first collaboration with director Gus Van Sant
Cast in a supporting role opposite John Travolta and Robin Williams in the comedy "Old Dogs"
Starred in the crime thriller "Armored"
Appeared in the ensemble crime thriller "Takers"