“One of the biggest challenges we face is staying kind with profound disagreement—and staying kind when a mechanism has been set up to make money and power out of hate.” — Penn Jillette

Penn Jillette (@pennjillette) is a cultural phenomenon as a solo personality and as half of the world-famous, Emmy Award-winning magic duo and Las Vegas headliners Penn & Teller.

Together since 1975, Penn & Teller’s live show spent years on Broadway and is now the longest-running headliner show in Las Vegas where it plays nightly at The Rio All-Suite Hotel & Casino. The pair has been awarded Las Vegas Magicians of the Year an amazing eights times.

As part of Penn & Teller he has appeared on hundreds of shows, from The Simpsons and Friends to Billions. He recently co-wrote an episode of the Emmy-winning Netflix series Black Mirror.

He co-hosted the controversial Showtime series Penn & Teller: Bullshit! which was nominated for thirteen Emmy Awards, won him a Writers Guild award, and was the longest-running show in the history of the network. He currently co-hosts the CW Network hit competition series Penn & Teller: Fool Us! which was nominated for a 2017 Critics’ Choice award.

Penn’s latest book, The New York Times Best Seller Presto! takes an insightful and very humorous look at his recent weight loss journey. His previous book, God No! Signs You Might Be An Atheist and Other Magic Tales, spent six weeks on The New York Times Best Sellers list.

His weekly podcast, Penn’s Sunday School, was the number one downloaded podcast on Apple Podcasts during its debut week, and was named a Best New Comedy Podcast by Apple Podcasts.

On the big screen, Penn produced the critically lauded 2005 documentary The Aristocrats, which features over 100 of the biggest names in comedy telling their versions of the dirtiest joke in history. He produced Tim’s Vermeer, which follows the journey of an eccentric inventor determined to solve one of the art world’s oldest mysteries. The Sony Pictures Classics release was nominated for a BAFTA and was shortlisted for the 2014 Oscars. He has recently completed the documentary Gambler’s Ballad profiling magic legend Johnny Thompson.

Penn & Teller have their very own star on the Hollywood Walk of Fame and triumphantly returned to Broadway recently with Penn & Teller On Broadway, which was the highest-grossing non-musical for the entirety of its run.

You can find the transcript of this episode here. Transcripts of all episodes can be found here.

Please enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform.

#405: Penn Jillette on Magic, Losing 100+ Pounds, and Weaponizing Kindness https://rss.art19.com/episodes/d7ddd8d5-ddfd-4a9c-b396-1ab266743185.mp3 Download

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What was your favorite quote or lesson from this episode? Please let me know in the comments.

SCROLL BELOW FOR LINKS AND SHOW NOTES…

Want to hear an episode with a friend Penn and I share? — Listen to my conversation with Brian Koppelman, co-writer/producer of Rounders, Billions, The Illusionist, and Ocean’s Thirteen. In the episode, we explore how he got started, how he handles rejection, his big breaks, creative process, and much more (stream below or right-click here to download):

#10: Brian Koppelman, Co-writer/Producer of Rounders, The Illusionist, Ocean's Thirteen https://rss.art19.com/episodes/a7042c78-d249-4a70-8be3-cf68760113ba.mp3 Download

SELECTED LINKS FROM THE EPISODE

Connect with Penn Jillette:

Penn & Teller | Penn’s Sunday School | Twitter

SHOW NOTES

How does Penn know our mutual friend Brian Koppelman, and what do they share in common? [08:10]

Who is James Randi, and how did he come to be such an influence on Penn? [10:57]

What can we do to guard against deceit by becoming more skeptical without becoming more cynical? [18:09]

Joking that journaling is “one way to teach yourself that you don’t remember things properly,” what got Penn to start keeping a journal at age 30, and how does he use journaling today? After 34 years, how does he benefit from the time he puts into the almost-daily practice? [24:37]

Confessing he has a visual memory so weak that it’s been “studied by people,” how does Penn compensate for this in his professional life? Does it give him a unique edge? [37:36]

What does the content of Penn’s dreams look or feel like? [43:14]

What led to Penn’s period of homeless wandering in his youth, how long did it last, and how did it differ from what we might think of as “homeless” in the modern context? [48:14]

What constituted Penn’s street performance that earned him “several grand a week” during this homeless period, how did he manage to consistently get a crowd of 300-500 people to watch him perform, and why is his distinctive voice a direct result of these performances? [52:30]

How did this period shape the way Penn sees the world today? What did it teach him about trusting other people and deescalating hostility? [58:43]

How young hippie hobo Penn defused a potentially violent confrontation with a pair of macho truckers in a Corn Belt diner using only his quick wits and a cold, sticky milkshake. [1:03:15]

Penn has never partaken of drugs or alcohol, which is a claim not many can make. To what does he credit this abstinence? [1:09:31]

How did Penn lose 0.9 pounds a day for four months under the direction of former NASA scientist Ray Cronise? [1:14:14]

What weight loss (and an illegal trip on NASA’s “Vomit Comet”) did to change Penn’s atheistic perspective on mind-body duality. [1:22:36]

What Penn’s — some would say extreme — version of intermittent fasting looks like. [1:27:31]

What did Ray Cronise mean when he said “You can’t outrun your mouth” while forbidding Penn to exercise during the four-month weight-loss regimen — and do I agree with this? (As an aside, it was determined that performing nightly 90-minute Penn & Teller shows burns a lot of calories, effectively nullifying Ray’s no-exercise rule.) [1:33:30]

Penn shares what he took away from lucky interactions with legendary theoretical physicist Richard Feynman and his fellow Nobel laureate Murray Gell-Mann. [1:38:24]

Why Richard Feynman (and possibly Bob Dylan) would pass Tim Jenison’s data points test. (Would you?) [1:48:14]

With so many projects from which to choose at any given time, how did Penn decide to put time into making the (in my opinion, excellent and very worth your while) documentary Tim’s Vermeer? What’s it about, and what were the obstacles faced along the way in trying to get it made? [1:50:58]

What be on Penn’s billboard? [1:59:25]

Parting thoughts, a seemingly impossible thought experiment, and Penn’s hope that we can stay kind to one another with profound disagreement in these divisive times. [2:00:55]

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