In 2005, Fox co-wrote and co-starred in the comedy Tennis Anyone? with Donal Logue. On August 11, 2006, he made his television standup debut on Comedy Central's Live at Gotham and in 2007 received the Jury Prize for best standup at the HBO Comedy Festival in Aspen, Colorado. In March 2008 he was featured in his own 1/2 hour special on Comedy Central: Comedy Central Presents: Kirk Fox. He appeared on The Tonight Show with Jay Leno in December 2008 and May 2009.