Caliendo was born in Chicago, Illinois, and was raised in Waukesha, Wisconsin, where he attended Waukesha South High School.
He is of Spanish ancestry.
After graduation from University of Wisconsin-Milwaukee, Caliendo began performing stand-up comedy, taking a job as a master of ceremonies at a local comedy club. Within a year he was headlining.
He made his network series debut on the 2000-2001 sketch comedy series Hype. He gained significant national exposure on the comedy series MADtv.
Frank currently stars on Frank TV, his own sketch show on the Turner Broadcasting System that began airing in November 2007. Frank is its host and performs in sketches in full makeup as characters he impersonates. Frank joked that he "wanted the show to be called The Chappelle Show [ sic ], but the lawyers wouldn't allow it," referring to the publicity he would likely receive from naming his show after another popular comedian.
In 2001 and 2002, Caliendo had a recurring role on FOX NFL Sunday, as a guest to comedian Jimmy Kimmel. Caliendo frequently appeared impersonating announcer John Madden during some of Kimmel's prognostication skits.
Caliendo appeared in the 2007 film The Comebacks. He plays John Madden and Al Michaels in the championship game between the Comebacks and The Gridiron Gang.
Caliendo’s spot-on impression of President George W. Bush earned him an invitation to perform during the 2007 annual White House Correspondents Dinner.
Brian Regan Impression
Farley As Batman
John Madden & Troy Aikman
John Madden Impression
John Madden's Letter To Santa
Kung Foo Cosby
Madden Surfing The Net