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Born in Memphis, Chester moved with his family to south Florida in the early 1980s. He then finished high school and college in Kansas, but only after he interned with the Walt Disney Company and the Kansas Film Commission. After moving to Hollywood in the mid 1990s, he secured his S.A.G. card by doing extra work in television and film. While currently developing several of his own projects, he is also the producer and host of My TV Show.