A Wild Card game against Pittsburgh in January 2003 saw Holcomb, playing for the Browns, become the third quarterback in playoff history to throw for more than 400 yards. He finished the game with 429 yards, a new postseason record for a regulation game. However, Tommy Maddox rallied the Steelers late in the game to overcome a 17-point deficit and defeat the Browns, 36-33.

In 2008, Holcomb joined his alma mater Middle Tennessee as the color commentator for the Blue Raider Radio Network. In addition, Holcomb has broadcast the TSSAA Blue Cross Bowl and was a broadcast member of the Music City Bowl Preview.