After working in several smaller jobs following college, Craig Kilborn hit the big time when was hired as a SportsCenter anchor by the cable sports network ESPN in 1993. He spent most of his time at ESPN working as anchor of the 1 AM EST version of SportsCenter and gained a large fan following in the process. In 1996 Kilborn was hired to host The Daily Show on Comedy Central, and it was here when he first generated controversy.

Kilborn's stint at the Daily Show had lasted only a couple seasons when another opportunity presented itself. David Letterman's production company World Wide Pants wanted to have Kilborn replace the retiring Tom Snyder on the Late Late Show on CBS. Kilborn accepted, and his last Daily Show episode aired on December 17, 1998. Kilborn hosted the Late Late Show for five years before resigning in August 2004 to participate in the film industry. Kilborn made his motion picture acting debut with a small role in Old School . In 2006, he appeared in three major motion pictures: The Shaggy Dog, The Benchwarmers, and Full of It.