[6] Jillette became disenchanted with traditional illusionist acts that presented the craft as authentic magic, such as The Amazing Kreskin on The Tonight Show Starring Johnny Carson.

At age eighteen, he saw a show by illusionist James Randi, and became enamored of his approach to magic that openly acknowledged deception as entertainment rather than a mysterious supernatural power.

[7] Jillette worked with high school classmate Michael Moschen in developing and performing a juggling act during the years immediately following their 1973 graduation.

The show was designed to appear to fall apart as it progressed; Jillette pretended to grow angrier with the crowd, and lighting effects and music would become increasingly chaotic, all building up to the point where he was dragged off stage and returned, handcuffed to a wheelchair, to deliver his last monologue.

In the show, the two analyze cultural phenomena, debunk myths, criticize people and aspects of society they deem "bullshit".

From January 3, 2006, to March 2, 2007, Jillette hosted, along with fellow atheist, skeptic, and juggler Michael Goudeau, a live, hour-long radio talk show broadcast on Free FM.

The show, Penn Radio, broadcast from his Vintage Nudes Studio in his Las Vegas home.

Signs You May Already Be An Atheist and Other Magical Tales was released and made the New York Times Best Sellers shortly after, in the week of August 28, in the 14th position.

[19] An avid upright bassist, Jillette frequently accompanies jazz pianist Mike Jones, who opens for the magician's Las Vegas show.

Jillette additionally performed at the famed Green Mill Cocktail Lounge to coincide with the album's debut.

In 2013, he returned for the All-Star Celebrity Apprentice season, where he successfully made his way to the finale, raising $663,655 for the charity of his choice, Opportunity Village.

[22] On April 5, 2013, Penn and Teller were honored with a star on the Hollywood Walk of Fame in the live performance category.

"[24]: 5:34 From 1987 to 1989, Jillette provided financial support to David and Jad Fair of the art rock band Half Japanese for their record label 50 Skidillion Watts.

"[25] In July 1999, Jillette was granted U.S. patent 5,920,923 for the "Jill-Jet", a hot-tub jet specially angled for allowing a woman to masturbate against the water stream.

[26] The abstract of the patent explains that a "discharge nozzle is located within the tub and connected to the outlet, mounted to the seat so that the discharged water from the circulation pump automatically aligns with and is directed to stimulation points (e.g., the clitoris) of the female user when the female user sits in the seat."

On the Penn Radio show, telling the listeners about the photo shoot for the Playboy article, Jillette mentioned that he has a Jill-Jet installed in a tub in his house, and that several of his female friends and friends' female spouses enjoy it a lot, but he is not aware of any other installations of a water jet in such a configuration anywhere else.

"[34] On the podcast Skepticality in 2012, Jillette said that he was considering changing the meaning of the red nail polish, telling his child it is for them.

[7] Jillette says that he has an addictive personality[35] and claims to have never had "so much as a puff of marijuana or a drop of alcohol" because he does not trust himself to do it in moderation.

He follows Joel Fuhrman's nutritarian diet, which means that he eats little or no animal products, no processed grains, and no added sugar or salt.

"[41] His atheism, he has explained, has informed every aspect of his life and thoughts, and as such is as crucial to him as theistic beliefs are to the devout.

Jillette does not dismiss all who do believe in God: in a 2008 edition of his Penn Says podcast, he expresses his appreciation for a fan who brought him the gift of a pocket Gideon Bible after a performance because he realized that this individual sincerely cared enough about him to try to help him.

[42] In January 2007, Jillette took the "Blasphemy Challenge" offered by the Rational Response Squad and publicly denied the existence of a holy spirit.

"The fact they sent me this email is something I need to be very ashamed of, and I need to change" adding "Many times when I identified as Libertarian, people said to me, 'It’s just rich white guys that don’t want to be told what to do,' and I had a zillion answers to that — and now that seems 100 percent accurate.

[57] In an op-ed for CNN after that year's general election, he stated that he "used to identify as Libertarian", but voted for Joe Biden.