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Perry grew up in Tampa, Florida, the son of a steelworker and a bookkeeper. He attended Jesuit High School, graduating as close to the middle of the class as it was possible to do with an even number of graduates, and then took a semester of college before joining the Navy to decide what he didn't want to do with his life. After his enlistment, he returned to the University of South Florida to earn a public relations degree he has yet to use. He alternates between local acting work in central Florida and writing self-deprecating autobiographies.