Simon has been performing almost non stop since his teenage years! Simon has been playing his original music with his band The Shadows of Doubt in pubs, music venues, theatres and festivals in London, across the UK and in Northern Spain. Described as a country singer at heart with a streak of the surreal running through him, his live show is engaging, energetic and constantly evolving. At it's best his performances can be gut-wretchingly moving and moments later silly, self deprecating and hilarious.

In 2017, he was a finalist in 2 UK comedy finals; the NATY's (New Act of the Year) at the Leicester Square Theatre and the UK Music Comedy Awards at the Lyric Theatre. He has performed at the Edinburgh Fringe and comedy festivals in Leicester, Liverpool, Hastings and Brighton as well as becoming a regular at The Camden Comedy Club.

In 2021 Simon performed his new show "How I found and captured Bigfoot during Lockdown" at The Etcetera Theatre as part of the Camden Fringe this August.