Caliendo was born in Chicago and grew up in Waukesha, Wisconsin, where he attended Waukesha South High School. He is of Italian descent.[2] Before he graduated from University of Wisconsin–Milwaukee, Caliendo began performing stand-up comedy at local night clubs and comedy clubs, he eventually became a master of ceremonies at a local comedy club. Within a few years, he was active on the college circuit. Between 2000 and 2001, Caliendo made his television debut on Hype, a sketch comedy series and later joined the comedy series MADtv.
From 2001 to 2004, he also made appearances on the KQ Morning Show's annual "Live from Las Vegas" simulcast, appearing on the panel throughout the show and reprising a few bits from his stand-up act. He has appeared on Garage Logic with Joe Soucheray; co-host Matt "Rookie" Michalski's has done various impersonations.
Fox NFL Sunday
On November 5, 2000, Caliendo appeared on Fox NFL Sunday; he returned again the same season on January 7 during the playoffs. In 2001 and 2002, Caliendo returned as a semi-regular guest. In 2003, Caliendo joined Fox NFL Sunday as a regular cast member, giving his predictions for the day's NFL games.
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.[4]
MADtv
Caliendo officially joined the cast of MADtv in 2001 as a repertory performer, for the seventh season. In 2002, Caliendo replaced Will Sasso on the show as the impersonator of George W. Bush.[5] Caliendo also was the announcer for the best of scenes on the MADtv season 1 DVD. Caliendo left MADtv before the 2006–2007 season.[6]
Caliendo starred on Frank TV, his own sketch show on the TBS that began airing in November 2007. Caliendo was its host and performed in sketches impersonating various celebrities.
In early 2008, TBS announced that they ordered eight more episodes, which ran later that year.[7] The show ended after the fifteenth episode, which aired on December 23, 2008.
Other appearances
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 filmThe 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.[9]
As of 2019, Caliendo is a recurring guest on the Barstool Sports podcast, Pardon My Take.
Personal life
Caliendo lives in Tempe, Arizona with his wife Michelle and their family.[10]