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, which ran for nine years. In 1991, he was given his own show, Get Your Own Back, which was shown on BBC One between 1991 and 2003, and was a game show consisting of one child contestant and an adult 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 1996, he was given his own show on ITV, Wake Up in the Wild Room. Phillips operates Chester Benson Productions, a production company which provides entertainment, removals and transportation services, and offers inflatables for hire, such as bouncy castles. Since May 2012, he annually co-hosts Let's Rock The Moor! alongside fellow broadcaster Pat Sharp. During the summer, he appeared as a panelist on Big Brother's Bit on the Side on Channel 5. In 2013, Phillips made a guest appearance in Sooty. Phillips plays himself in an award-winning mockumentary webseries called Getting Back with Dave Benson Phillips which began in 2017. The series by Andrew River was invited to showcase at MCM London Comic Con and the cast includes Pat Sharp and Ewen MacIntosh. The series and spin off In Production are available to watch on YouTube. He has most recently been seen working as a professional wrestler, after having also done so whilst working as a blue coat at Pontins.
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 porn TV sex line, and that he was no longer being hired because he had had a nervous breakdown. In 2017 Phillips spoke with the Chair of the Culture, Media and Sport Select Committee on an inquiry into fake news.
In August 2014, Benson-Phillips was one of 200 public figures who signed a letter to The Guardian expressing their hope that Scotland would vote to remain part of the United Kingdom in September's referendum on that issue.
