Patrick Dempsey

A gawky teen movie star who faded away before reemerging as a sexy small-screen player, Dempsey did regional theater before moving to Hollywood. In the late '80s he appeared in a number of films including In the Mood and Loverboy, which both featured him as a youth involved with older women. In a case of life imitating entertainment, the actor married his manager Rocky Parker when he was 21 and she was 48. (The union ended in divorce.) Although he made the transition to adult parts, they were mostly in TV-movies and direct-to-video duds. High-profile recurring roles on Will & Grace and Once and Again in the early '00s made him a familiar small-screen face, and in 2005 he became a star once again as a dreamy doctor involved in an on-again, off-again romance on the medical drama Grey's Anatomy. His off-screen love life was much simpler, with his happy marriage to makeup artist Jillian Fink.