Jupp won "So You Think You're Funny?, Leicester Mercury Comedian of the Year" in 2001, and was a Perrier Award "Best Newcomer" nominee in 2003, for his show "Gentlemen Prefer Brogues". He claimed to have bluffed his way onto an England cricket tour to India, as the cricket correspondent for BBC Scotland, and the "Western Mail" during his appearance on "Celebrity Mastermind", and again in an appearance on "Test Match Special" in 2011.