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 9 years.
In 1991, he was given his own show, Get Your Own Back, which was shown on BBC One (and later CBBC) between 1991 and 2003, and was a game show consisting of one child contestant and one of their peers (such as a relative or teacher) who, in the child's eyes, had done something unreasonable, and for which the child wanted revenge. In 1999, the show was nominated for a BAFTA.
In 2009, Benson Phillips was the victim of a death hoax perpetrated across the internet which maintained that he had died in a car crash. There were other false rumours that he was presenting on a soft pornTV sex line, and that he was no longer being hired because he had had a nervous breakdown.