Benson Phillips became interested in showbusiness while working as an usher at the Polka Children's Theatre in Wimbledon, London, and began his career as an entertainer by busking and performing at children's parties. He subsequently went on to work for Pontins as a Bluecoat, and a Children's Uncle for Haven Holidays. While working at Haven, a talent scout saw him perform, and he was invited by BBC Manchester to audition for "Play School". His audition was successful, but the show was pulled out of production shortly after he signed the contract; however, it was recommissioned as "Playbus" (later renamed to "Playdays"), which ran for nine years.