Rupert’s first performances began in repertory theatre when he played Fowler in Another Country. He went on to play Ernst in Cabaret and Algernon in The Importance of Being Earnest.

He made his West End debut as one of the Henrys in The Sloane Ranger Review, based on the books by Ann Barr and Peter York, devised and directed by Ned Sherrin at the Duchess Theatre.

Rupert’s theatre work also includes; Herman Goering in Unpainted Pictures, Marston Dawlish in Naked Justice, by John Mortimer at the West Yorkshire Playhouse, Victor in Private Lives and RSM Riddick in the Tunes of Glory tour for Michael Lunney at the Middle Ground Theatre Company.