Born in England in 1974, Will was partially brought up in America, where his father was in the Army. It was here that he picked up the accent for his comic persona, the motivational speaker Chris John Jackson. He went to Eton College in England and the Oxford School of Drama and started to gain stage notice in 1999. He spent much time at London's Battersea Arts Center, noted as a springboard for offbeat comedy, and this is where he honed the character of 'Jackson'. He took it to the Edinburgh Festival, planning initially on only a week's booking as a friend was running another venue and there was a vacant slot. However, it won him the Perrier Comedy Award for 2004.