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Oliver began singing professionally at the age of 16 and has worked extensively throughout the UK both as a solo performer and collaborator since that time. His vocal and guitar session work includes Pennis Pops Out (BBC2), Bill Hicks (US live video title music), Tribute To The Seventies (Carlin Music Library), Who Killed Mr Brynes (Simpsons' Euro Promo), Theatre of Dreams (principal vocal/promo) and Casper The Musical (original cast recording).

In 1995, after receiving his acting diploma, OIiver directed numerous plays including Brecht's Man Equals Man, Trainspotting and A Midsummer Night's Dream, for which he received critical acclaim both as director and for his performance of Bottom. In 1999 he played his first West End lead at the Shaftesbury Theatre in the musical Casper. He also toured with the show throughout the UK. Oliver is currently working on a solo album of his own compositions.