Penn Jillette, the talking magician, is the larger of the two (6'6"/1.98 m to Teller's 5'9"/1.75 m), and was born March 5, 1955 in Greenfield, Massachusetts. He attended Ringling Brothers Barnum and Bailey Greatest Show on Earth Clown College (he has apologized for this). He became disillusioned with the type of magic acts that present magic as "real" by watching The Amazing Kreskin on the Johnny Carson show. He attended a performance by The Amazing Randi with Teller at the age of eighteen which suggested the idea of presenting magic as an openly acknowledged trick rather than as a mysterious power.
Penn appeared as "Drell" on the TV series Sabrina the Teenage Witch and was a voice announcer for the U.S. based cable network Comedy Central in the early 1990s. One of his earliest guest roles was on Miami Vice.
Penn has collaborated with avant-garde musicians The Residents. Penn's own band is called The Captain Howdy. He was also a member of Bongos, Bass, and Bob, in which he played bass guitar. Penn is also the owner of the entire catalog of the band Half-Japanese, headed by Jad Fair. He is featured in the Half Japanese documentary "The Band that Would be King". Penn and fellow Clown College alumnus Steven Banks collaborated in writing Love Tapes – a romantic comedy stage show which premiered February 2005 at Sacred Fools Theater in Hollywood.
Penn married television producer Emily Zolten during an impromptu ceremony at a Las Vegas wedding chapel on November 23, 2004. Their first child, Moxie CrimeFighter Jillette, was born on June 3, 2005.
On October 25, 2005, Infinity Broadcasting announced that Penn Jillette will be hosting a live hour-long radio talk show starting in January 2006, which will be heard on various radio stations that are now (or will soon be) known as Free FM: WXRK New York, WCKG Chicago, KIFR San Francisco, WJFK-FM Washington, D.C., WKRK Detroit, KPLN San Diego, and WHFS Baltimore. He will also be heard on KSFN (AM) Las Vegas.