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From 2000-2002, he starred in the television sitcom, Spin City.
His most famous role on television was playing Charlie Harper on the comedy sitcom, Two And A Half Men, from 2003 until 2011, when he was fired from the show due to a public feud with the show's creator and was replaced by Ashton Kutcher. He is currently on the television comedy, Anger Management.
Some of his other movie roles include Terminal Velocity, Navy SEALs, Scary Movie 3 and its sequels, and Hot Shots and its sequel.