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Penn Jillette Says He Lived Homeless for Two Years as Bob Dylan Impersonator

Club Random · Penn Jillette | Club Random Classics with Bill Maher · July 16, 2026
Penn Jillette Says He Lived Homeless for Two Years as Bob Dylan Impersonator
Club Random
Club Random
Penn Jillette | Club Random Classics with Bill Maher
"I was a huge Bob Dylan fan. I read about Bob Dylan. I wanted to be like Bob Dylan. I didn't find out for years. I didn't find out years later that Bob was lying. When Bob said he worked in the carnival, he was lying. I worked in the carnival. When Bob said he hopped trains, he was lying. I hopped trains."
Penn Jillette reveals he spent two years homeless, sleeping in alleys and hopping trains while trying to emulate Bob Dylan's fabricated origin story. He survived by street juggling and calling his parents collect daily, living the hobo lifestyle Dylan only claimed to have experienced. He later discovered Dylan had invented much of his working-class backstory while actually coming from a middle-class appliance store owner's family in Minnesota.

About this episode

Bill Maher sits down with Penn Jillette, the magician and professional skeptic, for a wide-ranging conversation that touches on religion, psychics, parenting, politics, and their shared histories in comedy. The episode reveals surprising personal details about both men, including Penn's two-year stint living homeless while emulating a fabricated Bob Dylan biography, hopping trains and sleeping in alleys while calling his parents collect daily. The conversation takes a fascinating turn when Maher challenges Penn on psychic phenomena, pressing him about a mentalist he saw perform with Barbra Streisand. Despite his career debunking supernatural claims alongside Amazing Randi, Penn admits there are some tricks he cannot fully explain, though he maintains they are likely sophisticated deceptions rather than genuine supernatural abilities. The two bond over their atheism, with Penn revealing Johnny Carson privately identified as an atheist and was a devoted fan of Penn's debunking show Bullshit. Penn shares the bittersweet story of being invited to screen The Aristocrats privately for Carson, only to have the comedy legend die the morning after their Sundance premiere. He also recounts turning down The Tonight Show with Johnny Carson over creative differences about leaving Teller seemingly dead before a commercial break, choosing artistic integrity over a career-defining appearance. On a lighter note, Penn discusses his 23-year run as the longest-tenured headliner in Vegas history, his evolution to veganism after losing 120 pounds, and his philosophy on parenting, arguing that parents have far less influence than commonly believed since immigrants' children don't develop their parents' accents. The conversation exemplifies the nonpartisan, intellectually curious approach that has defined Maher's career resurgence.

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