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Riddle decided he wanted to be an actor after he wrote to silent screen star Billie Dove and she responded with an autographed picture. In addition to becoming an actor, Riddle started a collection of movie memorabilia. It eventually grew to more than 1,700 items that he donated to his alma mater, Murray State University in Kentucky, in 2001. Riddle's first professional job was in summer stock in Allentown, PA. He roomed with Jack Lemmon, who became a lifelong friend. He also worked in four Elvis Presley movies. In all, Riddle appeared in some two dozen movies and over 400 television shows.