Dillon's furrowed brow and soulful eyes were featured in a string of rebellious adolescent flicks (Over the Edge, Tex, Rumble Fish) that turned him into a teen idol, a sort of '80s James Dean. But unlike many of his contemporaries — notably his Outsiders' costar Tom Cruise — his career as a leading man stalled as the decade wore on. The pretty boy reinvented himself in the '90s as a capable character actor, tackling a variety of big-screen supporting roles and faring especially well in comedies, including his hilarious turns as a dimwit Hollywood star in In & Out and an unscrupulous private eye with unforgettable teeth in There's Something About Mary. Despite his busy acting schedule, he tried his hand behind the camera as the writer-director-star of 2002's little-seen City of Ghosts. In 2005, after a quarter century of steady if not critically acclaimed work, Dillon earned the respect of his peers as well as Oscar and Golden Globe nods for his performance as a racist cop in Crash.