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An avid upright bassist, Jillette frequently accompanies jazz pianist Mike Jones, who opens for the magician's Las Vegas show. On March 16, 2018, Jones released a live jazz album with Jillette entitled The Show Before the Show which consisted of ten tracks played by the duo at the Rio Las Vegas. Jillette additionally performed at the famed Green Mill Cocktail Lounge to coincide with the album's debut.

In December 2014, Jillette's blood pressure landed him in the hospital. By his birthday, March 5, 2015, he had lost 105 lb (48 kg). He follows Dr. Joel Fuhrman's Nutritarian diet, which means that he eats little or no animal products, no processed grains, and no added sugar or salt. Penn is featured in Eating You Alive, a 2016 American documentary about food and health.

Jillette stated that there is not enough information to make an informed decision on global warming, that his gut told him it was not real, but his mind said that he cannot prove it. As of 2014, he has changed his position and now believes that climate change is occurring.

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. On April 5, 2013, Penn and Teller were honored with a star on the Hollywood Walk of Fame in the live performance category. Their star, the 2,494th awarded, is near the star dedicated to Harry Houdini. The following day they were recognized by the Magic Castle with the "Magicians of the Year" award.

Jillette was one of the contestants on The Celebrity Apprentice season 5, beginning on February 19, 2012. He was fired from the show by Donald Trump during the Week 11 episode. Also on February 19, 2012, along with Michael Goudeau, he started the podcast Penn's Sunday School.

Penn credits magician and skeptical activist James Randi for his career. During an interview at TAM! 2012, Penn stated that "If not for Randi there would not be Penn & Teller as we are today." He went on to say that "Outside of my family... no one is more important in my life. Randi is everything to me."

Jillette endorsed Libertarian Party nominee Gary Johnson for President in 2012 and 2016. However, he participated in vote swapping in 2016 by voting for Democratic nominee Hillary Clinton in the swing state of Nevada, in exchange for "10 or 11" of his friends promising to vote for Johnson in blue states like California and New York.

In direct response to questions about his red fingernail, Penn has stated "People are asking about my fingernail. Wear my Dad's ring and my Mom's nail polish. Just for remembrance and respect." The color he uses is Jelly Apple Red (#054) by Essie. On the podcast Skepticality in 2012, Jillette said that he was considering changing the meaning of the red nail polish, telling his daughter it is for her. During his appearance on the Chopped Tournament of Stars (2014), he effectively told the story of his mother suggesting he get a manicure for the reasons stated above, and said that he kept it in respect for her.

On August 16, 2011, Jillette's book God, No! 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.

During 2010–2011, Jillette did a bi-weekly show on Revision3 called Penn Point.

In 2008, Jillette was a contestant on Dancing with the Stars, paired with professional dancer Kym Johnson. He was the first celebrity to be eliminated. A reference to his large feet as a sign of another large body part was censored in the West Coast airing.

Jillette is an atheist, libertarian (he has stated that he may consider himself to be an anarcho-capitalist), and skeptic, as well as an adherent to Ayn Rand's Objectivist philosophy, as stated on his Penn Says podcast. Jillette is a fellow at the libertarian think tank the Cato Institute and has stated that he "always" votes Libertarian. In January 2007, Jillette took the "Blasphemy Challenge" offered by the Rational Response Squad and publicly denied the existence of a holy spirit.

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. The most notable recurring segment of the show was "Monkey Tuesday" and later "The Pull of the Weasel". On March 2, 2007, Jillette announced that he would no longer be doing his radio show. He stated that he is a "show biz wimp" and decided to stop doing the show so he could spend more time with his children.

During the 2006–07 television season, Jillette hosted the prime-time game show Identity on NBC.

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." An article in the June 2006 issue of Playboy shed additional light on the invention. Originally, it was to be called the "ClitJet"; however, he stated that "Jill-Jet" was more suitable because it included his name in the title.

In 2005 with actor Paul Provenza, Jillette co-produced and co-directed The Aristocrats, a documentary film tracing the life of an obscene joke known as "The Aristocrats". It principally consists of a variety of comedians telling their own versions of the joke.

In 2005, he wrote and read an essay for National Public Radio claiming that he was "beyond atheism. Atheism is not believing in God... I believe there is no God." 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 encourages open discussion, debate, and proselytizing on the issue of God's existence, believing that the issue is too important for opinions about it to remain private. Jillette does not dismiss all who do believe in God: a 2008 edition of his Penn Says podcast 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.

Starting in 2003, Jillette, along with Teller, began producing and hosting the show Penn & Teller: Bullshit! on Showtime. In the show, the two analyze cultural phenomena, debunk myths, criticize people and aspects of society they deem "bullshit".

Jillette created a private recording studio in his Las Vegas home. The addition, designed by Outside The Lines Studio and built by Crisci Custom Builders between October 2003 and June 2004 as part of his Las Vegas home, was named Vintage Nudes Studios by Jillette for playing cards that he had collected. The cards are displayed in the interior design in a manner which is meaningful to magicians. The studio was home to Free FM's Penn Radio show, and was the home of the Penn's Sunday School stream and podcast until it was demolished in 2016, along with his former home, "The Slammer".

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. The patent expired in September 2018. He has credited Debbie Harry of Blondie for suggesting the idea, as the two of them were once in a hot tub and Harry made a remark about changing the jets for a woman's pleasure. Jillette liked the idea enough to pursue a patent application at the USPTO under the patent title "Hydro-therapeutic Stimulator".

For a brief time in 1997, Jillette wrote bi-weekly dispatches for the search engine Excite.com. Each column ended with a pithy comment identifying which of the Penn & Teller duo he was. (For example: "Penn Jillette is the half of Penn & Teller that's detained at airports.") Jillette made a habit of linking many words in his online column to wacky sites that generally had nothing to do with the actual words. The columns are no longer available on the current Excite.com site, but have been republished with permission at PennAndTeller.com.

Starting in 1996, Jillette had a recurring role on Sabrina the Teenage Witch as Drell, the head of the Witches' Council. He and Teller both appeared in the pilot with Debbie Harry as the third member of the Council. The show was created by Jillette's friend Nell Scovell.

In 1994, Jillette purchased a house in the Las Vegas Valley and dubbed it "The Slammer". It has been featured in dozens of television shows and articles and was designed by his friend Colin Summers. He formerly recorded music there, and conducted his radio show at the studio inside "The Slammer". In 2016, he sold "The Slammer" so that his family could move to a less remote location.

Jillette was a contributor to the now-defunct PC/Computing magazine, having a regular back-section column between 1990 and 1994.

Jillette was the primary voice announcer for the U.S.-based cable network Comedy Central in the 1990s.

While the off-Broadway hit was running, in 1988 Jillette was in the band Bongos, Bass and Bob. He played bass; bongos were by Dean J. Seal; and guitar was by Rob "Bob" Elk (Running Elk). The latter two became the a cappella comedy duo Mr. Elk and Mr. Seal after the band broke up due to Jillette's movie commitments. They recorded an album with Kramer at Noise New York called Never Mind the Sex Pistols, Here's Bongos Bass and Bob (What on Earth Were They Thinking?). It was released to almost no notice outside of a mention in Spin Magazine, but was immortalized with a claymation video of the single, "Oral Hygiene".

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. This allowed the band to release the albums Music to Strip By, The Band that Would be King and Charmed Life. When asked about his assistance Jillette said, "anybody who listens to Half Jap becomes a fan."

Jillette served as host and presenter of the first touring performance by avant-garde band the Residents in 1983. The performance (titled The Mole Show and based on their "Mole trilogy" of albums) featured Jillette coming out between songs telling long and intentionally pointless stories. 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. During one performance, an audience member assaulted Jillette while he was handcuffed to the wheelchair. In later years, Jillette would contribute to two documentary films about the Residents.

Jillette worked with high school classmate Michael Moschen in developing and performing a juggling act during the years immediately following their 1973 graduation. In 1974, Jillette graduated from Ringling Bros. and Barnum & Bailey Clown College. That same year, he was introduced to Teller by Weir Chrisemer, a mutual friend. The three then formed a three-person act called Asparagus Valley Cultural Society which played in Amherst and San Francisco. In 1981, he and Teller teamed up as Penn & Teller, and went on to do a successful Off Broadway and later Broadway theatre show called "Penn & Teller" that toured nationally.

Penn Fraser Jillette (born March 5, 1955) is an American magician, actor, musician, inventor, television personality, and author, best known for his work with fellow magician Teller as half of the team Penn & Teller. The duo has been featured in numerous stage and television shows, such as Penn & Teller: Fool Us and Penn & Teller: Bullshit!, and is currently headlining in Las Vegas at The Rio. Jillette serves as the act's orator and raconteur.

Jillette was born in Greenfield, Massachusetts. His mother, Valda Rudolph Jillette (née Parks; 1909–2000), was a secretary, and his father, Samuel Herbert Jillette (1912–1999), worked at Greenfield's Franklin County Jail. Jillette became an atheist in his early teens after reading the Bible. He was subsequently asked to leave the church, after asking questions in a youth group that purportedly also made skeptics of his peers. 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. Jillette regularly acknowledges Randi as the one person on the planet he loves the most besides members of his family.