Simon Bird started his comedy career with the Cambridge Footlights in 2004, as a writer of their touring show Beyond A Joke. He appered in 2005 show Under The Blue, Blue Moon and 2006's Niceties.

He took part in Chortle's national student comedy awards for four years in a row: 2005, 2006, 2007 and 2008, coming second in his final attempt with a routine mocking his repeat entries.

He played the part of Will in E4’s comedy The Inbetweeners, alongside Joe Thomas. The pair also have a sketch group, House Of Windsor, with Johhny Sweet.