Actor whose prominent acting roles include There's Something About Mary, Herbie: Fully Loaded, The Outsiders and You, Me and Dupree. He was nominated for an Academy Award for Best Supporting Actor for his role in the 2004 film Crash.
He earned his first acting role after being discovered in the halls of his New York high school.
He became a teen icon by playing roles in film adaptations of S.E. Hinton's work and was also in Drugstore Cowboy.
He dated actress Cameron Diaz from 1995 to 1998. In 2014, he began a long-term relationship with choreographer Roberta Mastromichele.
He starred as Bob in Gus Van Sant's adaptation of the James Fogle novel Drugstore Cowboy.