He has appeared on Garage Logic with Joe Soucheray; co-host Matt "Rookie" Michalski's has done various impersonations.

On November 5, 2000, Caliendo appeared on Fox NFL Sunday; he returned again the same season on January 7 during the playoffs.

On August 2, 2012, Caliendo announced he would not be on Fox NFL Sunday for the 2012 season;[3] he was replaced by Rob Riggle.

[6] Caliendo starred on Frank TV, his own sketch show on the TBS that began airing in November 2007.

Caliendo's impression of President George W. Bush earned him an invitation to perform during the 2006 annual Radio-Television Correspondents Dinner.

[8] Caliendo appeared in the 2007 film The Comebacks as "Chip Imitation" who impersonates John Madden and Al Michaels in the championship game.

During The Comedy Festival Caliendo hosted a special called The Comedy Festival Presents: Funniest Movies of the Year 2008; from Caesars Palace, he introduced the top ten list for funniest films of 2008 based on an Internet poll.