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Pip first began acting as a teenager in Peoria, Illinois. Pip is a former member of the famed Second City National Touring Company. He has also appeared in commercials, Frank TV, Gay Hunt and the feature film, Butch Camp starring Judy Tenuta. Pip co-wrote and stars in the 2012 Web series, Failing Upwards. Pip's stage credits include the national tour, as well as, the West End production of Showboat (directed by Hal Prince and choreographed by Susan Stroman). Other credits include Joe's Garage, Schoolhouse Rock Live! And Women Behind Bars. He has performed in North America, South America, London, England and Vienna, Austria.