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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
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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.
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Penn Jillette | Club Random Classics with Bill Maher

August 3, 2026 · 1h 29m · 3 Egleze moments
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