Holland started performing stand-up comedy in 1991, making his debut at The Comedy Café, Rivington Street, London. In 1993, he was briefly managed by Eddie Izzard. In Holland's first year at the Edinburgh Fringe his one-man show won the Perrier Best Newcomer award and good notices. Later in the autumn of 1993, Holland supported Eddie Izzard on his national tour. In 1994, Holland returned to Edinburgh. In 1996, his show at the Edinburgh festival was nominated for the Perrier Award. Holland returned to the Edinburgh festival in 2006. In October 2012 Holland recorded his first stand up DVD at the Court Theatre in Tring.