Abruptly departed: Charlie Sheen Played: Jon Cryer's character's playboy brother, Charlie Harper Lasted: Eight seasons (2003-11) Why he left: After months of personal problems and tabloid terror stories, Sheen was put on hiatus from the hit CBS sitcom. Sheen then appeared on Alex Jones' radio show and threw down some fighting words for "Men" producer Chuck Lorre. Soon, after a slew of high-profile TV interviews and the birth of the "Sheen's Korner" webcasts, he was fired from the show for alleged breach of contract. How it went down on air: Charlie Harper is killed off screen by a moving train. Showrunners promptly replaced him with Internet tycoon Walden Schmidt (Ashton Kutcher, "That 70s Show"), who buys the old Harper house and moves in with Alan (Cryer).
Greg Gayne / Warner Bros.