milestones
Year
Milestone
 
Grew up in Mamaroneck, New York
1979 
"Discovered" at age 14 while cutting class in junior high school by casting director Vic Ramos; made screen acting debut, "Over the Edge"
1980 
Played hunk who deflowers Kristy McNichol in camp drama "Little Darlings"
1980 
Cast as the bully in "My Bodyguard"
1982 
TV debut in "American Playhouse" (PBS) production of "The Great American Fourth of July and Other Disasters"
1982 
Played titular character in "Tex", rare Disney film to tackle subjects like sex, boozing and fighting; first of three alienated teens Dillon portrayed in films based on S.E. Hinton novels
1983 
Starred as troubled teen leader of "The Outsiders", a Francis Ford Coppola film that launched careers of Tom Cruise, Rob Lowe, C Thomas Howell, Patrick Swayze and Ralph Macchio; based on a Hinton novel of the same name
1983 
Played alienated teen living in his brother's shadow in the mostly black and white "Rumble Fish", another Coppola film based on a Hinton book
1984 
Proved he could play non-hoodlum characters in the popular comedy "The Flamingo Kid"
1985 
Broadway debut in "The Boys of Winter", a play set in Vietnam
 
Directed rock videos for several bands including Dinosaur Jr
1989 
Won rave reviews for his searing portrayal of a junkie who robs drugstores to support his habit in the critically acclaimed "Drugstore Cowboy"; first collaboration with director Gus Van Sant
1992 
Played dim-witted Seattle grunge rocker in the sweet and funny ensemble comedy "Singles"
1993 
Starred as Con Ed worker trying to marry off his ex-wife in the romance "Mr. Wonderful"
1993 
Played schizophrenic homeless man in the drama "The Saint of Fort Washington" opposite Danny Glover
1995 
Starred as Nicole Kidman's doomed husband in Van Sant's black comedy "To Die For"
1997 
Featured as platinum-tressed actor who announces during Oscar telecast his closeted high-school English teacher is gay in the hit comedy "In & Out"
1997 
Directed episode of the HBO drama "Oz"
1998 
Announced plans to make feature directorial debut with "City of Ghosts" (still in development as of 2000)
1998 
Played popular guidance counselor wrongly accused of raping two students (Neve Campbell and Denise Richards) in the campy thriller "Wild Things"
1998 
Starred as sleazy private detective hired to track down Cameron Diaz (then his real-life girlfriend) in the blockbuster comedy "There's Something About Mary"; had memorable scene where he revived a dead dog
2001 
Co-starred in the ensemble of "One Night at McCool's", about three men whose lives are changed by the same woman
2001 
Had featured role in the independent film "Deuce's Wild"
2002 
Made feature directorial debut with "City of Ghosts;"also co-starred
2005 
Starred in Paul Haggis' directorial debut "Crash," a multicharacter study of L.A. race relations; earned Oscar, Golden Globe and SAG nominations for Best Supporting Actor
2005 
Cast in the Disney feature "Herbie: Fully Loaded" with Lindsay Lohan and Michael Keaton
2006 
Co-starred with Kyra Sedgwick in the Kevin Bacon directed "Loverboy"; premiered at Sundance (lensed 2003)
2006 
Played a newlywed married to Kate Hudson in the comedy "You, Me and Dupree"
Photo Galleries
Lauren and Heidi of MTV's "The Hills"
Jeff Lipsky/MTV

TV's Lovely Ladies

Check out the women that keep us tuning in.