Rich was born in the Bronx to first generation Italian-Americans who moved to Redwood City, CA when he was three years old. Rich's early dreams were on the Little League Field – winning the City Championship as an all-star Shortstop. After discovering an amazing talent for mimicry, the dream shifted to a lifelong passion for show biz. Classmates at Sequoia Highschool soon recognized the funny guy in their midst and Rich Natole as Class Clown was asked to do everything from star in the school shows to announce the football games as Howard Cosell.

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