Finally broke through on television after a couple failed shows as a co-star alongside Charlie Sheen on the CBS sitcom smash hit, Two and a Half Men.
He skipped college and left to study acting in London after graduating high school.
He gained fame after appearing in the film Pretty in Pink.
In 1999, he married Sarah Trigger with whom he had one child. Following their divorce, he married Lisa Joyner in 2007, and the couple adopted a daughter in 2009.
He co-starred in Two and a Half Men with Charlie Sheen.