Jillette, the larger, more talkative half of Penn & Teller, was born in Greenfield, Massachusetts. His mother, Valda R. (née Parks), was a secretary, and his father, Samuel H. Jillette, worked at a correctional facility. 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.

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 Brothers and Barnum & Bailey Clown College. That same year, he was introduced to Teller by Weir Chrisimer, a mutual friend. The three then formed a three-person act called Asparagus Valley Cultural Society which played in Amherst, Massachusetts and San Francisco, California. In 1981, he and Teller teamed up as Penn & Teller, and went on to do a famous off-Broadway show.

In 1994 Jillette purchased a home in Las Vegas 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 currently records music there, and previously conducted his radio show at the studio inside "The Slammer".

Jillette was also a regular contributor to the now-defunct PC/Computing magazine in the early 1990s, having a regular back section column between 1990 and 1994. True to form, the columns were often as much about Uma Thurman as actual PC computing issues. Jillette and PC Computing parted ways over a dispute with a new editor. Jillette felt the new editor was trying to tell him how to write his column and what topics he should be covering. Jillette asserts that he is unsure if he was fired or if he actually quit.

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

Starting in 1996, he 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 (all were the witches council). The show was created by Jillette's friend Nell Scovell.

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 2003, Jillette, along with his partner Teller, began producing and hosting the show, Bullshit!. In the show, the two analyze cultural phenomena, debunk myths, criticize people and aspects of society they deem "bullshit".

In 2005 with actor Paul Provenza, Jillette co-produced and co-directed The Aristocrats (2005), a documentary film tracing the life of a dirty joke known as "The Aristocrats".

He occasionally notes with irony that he lives and works in Las Vegas, but he does not gamble (though he did lend his name to a book on how to cheat at poker).

He claims never to have used recreational drugs or alcohol. He is, however, an advocate of the legalization of all drugs and discontinuing the War on Drugs.

Jillette is an outspoken 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. In January 2007, Jillette took the "Blasphemy Challenge" offered by the Rational Response Squad and publicly denied the existence of a holy spirit.His cars' license plates read "atheist", "nogod", and "godless". "Strangely enough, they wouldn't give me 'Infidel,'" he says.

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 welcomes and even 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, however, 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.

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 the radio station brand known as Free FM. The show, Penn Radio, broadcast from his Vintage Nudes Studio in Jillette's 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, on Free FM, 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 kids Zolten Penn Jillette and Moxie CrimeFighter Jillette. He made very clear that he was not fired.

During the 2006—07 television season, Jillette hosted the prime time game show "Identity" on NBC-TV. As of now, NBC states on its website that it plans for "Identity" to return to its prime time schedule soon, although a firm premiere date for the show's second season has not been announced.

Jillette was a contestant on the 2008 edition of Dancing with the Stars. He was the first male celebrity to be eliminated.

Jillette has stated that there is not enough information to make an informed decision on global warming, and that it is an emotion vs. logic issue. However, he has later accepted anthropogenic factors as a likely component in the current warming as well as the imperative to act on it, but clarified that his ignorance and reluctance to make a complete judgement is related to the political side of the debate.

In 2009, Jillette did a spoken guest appearance on a song by Pakistani rapper Adil Omar. The song was titled "Spookshow" and produced by DJ Solo of Soul Assassins. The lyrics condemn religious extremism and encourage skepticism. It is set to be featured on a compilation album by Thick Syrup Records alongside artists like Matt Cameron of Soundgarden, Pearl Jam, Half Japanese and more.

On May 24, 2010, Jillette began a daily show on Revision3 called Penn Point.

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

In July 1999, Jillette was granted for the "Jill-Jet", a hot-tub jet specially angled for a woman's pleasure. 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 patent application at the USPTO under the patent title "Hydro-therapeutic stimulator".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.

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 at "The Slammer", and that several of his female friends and friends' spouses enjoy it a lot, but he is not aware of any other installations of a water jet in such a configuration anywhere else.

Speculation arises from Jillette's red fingernail on his left hand. From a FAQ from Penn & Teller's official website, there are three common answers:

1. It means he once shot a man for asking personal questions.
2. When Jillette first began performing, his mother told him to get a manicure because people would be looking at his hands. In response to this, he had all of his nails painted red as a joke. The one remaining red fingernail is in honor of his mother.
3. It's just cool and can also sometimes provide excellent misdirection.

On the episode of Penn Radio broadcast on November 29, 2006, Jillette related the real story behind his red fingernail. It began as a joke with his mother. When he was 18 years old, his mother advised him to keep his hands looking nice, since he then was working as a magician and his audience would be looking at his hands. Jillette colored the single nail red and showed it to his mother. He has continued to paint that single nail to the present. The color he uses is Jelly Apple Red (#054) by Essie.

On the 26 March 2009 Penn Says titled "Painting My Fingernail" he said:"You know, I've been wearing my fingernail red on my left hand for probably close to forty years now. Certainly the vast majority of my life. And when people ask me why I have a red fingernail, I usually answer that it means that I killed a person for asking personal questions. You know, that's the joke I always use. But the real reason is, and the real reason has been distorted over the years. It's changed, the real reason. My mom, when I was first starting doing magic and juggling when I was a teenager, I was doing little card tricks for her and juggling. You know, go into the back yard and make her watch a trick fifty times till I happened to hit it. Very indulgent she was. She told me, her suggestion on show business was that I should keep my hands really nice. If you want people to be staring at your hands with these tricks you're doing you should keep your hands really nice. You should take really good care of them. Make sure the nails look really nice. So I took some of her nail polish. And in order to mock her, to annoy her, to irritate her, I don't even remember now whether I painted all my nails red, or I painted that one nail red. And said is this what you mean? Doesn't that look nice? Isn't that pretty. And of course she was jokingly disgusted. And I decided I liked it. And I kept it. And I kept it. And I kept it, and now my mom died almost ten years ago. And now it's kind-of morphed into this kind-of memory. When I look at the red fingernail I think about it being my mom's nail color. Which I don't think it is. I don't even know how much nail polish she wore."

He was once known to say that people pay so little attention to the important part of a trick that they "wouldn't even notice if you had painted your finger nail red", in reference to how people pay attention to the result of misdirection (as intended) instead of the cause.

Filmography

• Into the Wild Green Yonder (2009)
• The Growth (2009)
• The Aristocrats (2005)
• Michael Moore Hates America (2004)
• Fantasia 2000 (2000)
• Fear and Loathing in Las Vegas (1998)
• Toy Story (1995)
• Hackers (1995)
• Car 54, Where Are You? (1994)
• Half Japanese - The Band That Would Be King (1991)
• Penn & Teller Get Killed (1989)
• Gandahar (1988)
• Tough Guys Don't Dance (1987)
• My Chauffeur (1986)
• Savage Island (1985)

Television

• The New Adventures of Superman
• "Illusions of Grandeur" (1 episode, 1994) ... Romick
• Friends
• "The One With the Cuffs" (1 episode, 1997) ... Encyclopedia Salesman
• The Drew Carey Show
• "See Drew Run" (1997) TV episode ... Archibald Fenn
• "Drew Meets Lawyers" (1995) TV episode ... Archibald Fenn
• Sabrina The Teenage Witch
• "First Kiss" (1997) TV episode .... Drell
• "Jenny's Non-Dream" (1997) TV episode ... Drell
• "Terrible Things" (1996) TV episode ... Drell
• "Pilot" (1996) TV episode ... Drell
• Babylon 5
• "Day of the Dead" (1998) TV episode ... Rebo
• Penn & Teller's Sin City Spectacular 1998—99
• "Hollywood Squares" (1999-2004) regular
• The Simpsons
• "Hello Gutter, Hello Fadder" (1 episode, 1999) ... himself
• Dharma & Greg (2001)
• Miami Vice
• "Prodigal Son" (1985) TV episode ... Jimmy Borges
• The West Wing
• "In the Room" (2004) ... himself
• Bullshit! (2003 - current)
• The Moxy Show (original voice of Flea; later replaced by an unidentified actor in some episodes)
• Identity (premiered in December 2006); returned on March 16, 2008 on NBC and will air for seven weeks every Friday at 8 p.m. ET.
• Real Time with Bill Maher (2006) TV episode ... himself
• Dancing with the Stars (2008) ... himself
• Numb3rs
• "Magic Show" (2008) TV episode ... himself
• "Glenn Beck" (Fox News)
• Handy Manny
• "Halloween/Squeeze's Magic Show" (2008) TV episode ... Magic Marty
• Penn & Teller Go Public (1985) TV program produced by Community Television of Southern California and aired on Public Television stations.

• Ramones - "Something to Believe In"
• Run D.M.C. - "It's Tricky"
• Katy Perry - "Waking Up in Vegas"
• Too Much Joy - "Donna Everywhere"
• Why Wait - "Rascal Flatts"

Music

• "The Horse You Rode In On" by Pigface
• "Spookshow" by Adil Omar