Simon grew up in Watford before attending Cambridge University in the mid-eighties. Early performances at university included a double-act called God and Jesus (with Stephen Cheeke, now a Bristol University lecturer). In 1992, he appeared in The Dum Show at the Edinburgh Festival alongside Steve Coogan, Patrick Marber, Stewart Lee and Richard Herring. He first came to wider attention as the host of experimental night Cluub Zarathustra in 1994.
Throughout the nineties, he performed lengthy sell-out runs at West End theatres (Lyric, Soho Theatre, ICA) and international festivals (Melbourne, Adelaide, Aspen, New York) of his wildly eccentric shows featuring alongside stand-up his characters including Alan Parker: Urban Warrior, The League Against Tedium and Buckethead. During this time he was nominated for the Perrier Award at the Edinburgh Festival and the Barry Award at the Melbourne Comedy Festival.
In 1996, he starred in ITV’s flagship stand-up show Saturday Live, won a Sony Gold Radio Award for his BBC Radio 1 series Alan Parker’s 29 Minutes Of Truth and was nominated for a British Comedy Award for his BBC2 show (co-written with Graham Linehan) London Shouting. He built upon this breakthrough success with several vehicles for his League Against Tedium character, including a Radio 1 series in 1997, the UK Play (BBC3) series FuturTV in 1999 and, most notably, the BBC2 series Attention Scum in 2001 – which was directed by Stewart Lee and nominated for a Golden Rose Of Montreux Award. In 2003 he had his own Radio 4 series, Where Did It All Go Wrong? and appeared alongside Steve Coogan in BBC2’s The Private Life Of Samuel Pepys. The following year saw a second series for Radio 4.
Simon has continued to perform worldwide with at least one new live show each year. His cannon of work has grown to include four DVD releases (IAMTV 2007 Hello 2007, Fylm Makker 2013, Fylm 2014), a book of one-liners and quips (How To Live, 2005), contributions to Banksy’s book Wall & Piece (2007) and an appearance as Alan Parker on dance music group The Orb’s Grey Clouds (Distinct’ive Records, 2007).