Chegwin performed in West End stage shows such as "Tom Brown's School Days" with Russell Grant and Simon Le Bon; "The Good Old Bad Old Days" with Anthony Newley; and "Captain Pugwash" by John Kennett at the King’s Road Theatre in 1973. He had a career as a singer, releasing singles on the Cherub and Pye record labels, such as 'I'll Never Fall in Love Again' (1977), but turned down an offer to front the band Kenny (who had a number 3 hit in the UK Singles Chart with "The Bump"). He also worked as a disc jockey for 194 Radio City in Liverpool, and worked at BBC Radio 1 on Tony Blackburn's weekend morning show for four years.