Dillon is a heavy-browed actor, serial dater, and ex-teen idol.
An Irish-American New York native, Dillon made his film debut in the 1979 flick Over The Edge and soon became a teen heartthrob thanks to roles in Tex and The Outsiders. Known for his thuggy sneer and dreamy looks, Dillon earned a steady stream of roles in '80s and '90s flicks although he never achieved the superstar status of other actors who emerged at around the same time, like Tom Cruise.
By the mid-1990s, Dillon had dropped out of the spotlight a bit, but stirred up controversy as the creepy guidance counselor who has a threesome with Neve Campbell and Denise Richards in 1998's Wild Things. Since then, he's bounced back and forth between comedies and dramas, like 1998's There's Something About Mary, and 2004's Crash (for which he was nominated for an Oscar). He can also claim the title of director now that he's released City of Ghosts, the flick he co-wrote and directed.
Dillon's womanizing tendencies in the '80s were as excessive as the decade. Until 1998, he was dating Cameron Diaz, but seems to have settled down a bit: he had a son Indiyo with former actress Michele Anderson in 2008. [Image via Getty]