 During his time at Trinity College, he began to get noticed in bars and clubs, with a long term residency at The Dorchester hotel, London.Stilgoe's first public engagement was at the Pizza on the Park, London in 2004.Following the performance, Dame Cleo Laine later called Stilgoe in to perform with her and husband Sir John Dankworth on their Radio 2 show Live at the Stables.