He began performing live comedy in 1997, with the Upper Class Rapper. He began as a character comic, before also doing observational comedy and compering. In October 2001 he presented a radio show pilot at the Bracknell comedy festival. He appeared on the Edinburgh Festival Fringe in 2000, 2001, 2003 and 2016. Steve Bennett reviewing for "Chortle" in 2000 said his character comedy, including Upper Class Rapper and Ludwig the Bavarian, was a string of one-liners. The show had "inspired gags", but was "sadly patchy". Bennett's review three years later, calling his work "pleasant enough" but lacking an edge, noted he had moved on from being a character comic and decided to instead base his comedy on real life. In 2001, he took part in an attempt to get into the Guinness Book of Records at Edinburgh as one of 45 comics onstage in 45 minutes. He created the website Perrier Bets in 2004 to take bets on who would win the Perrier Award at Edinburgh.