Download the PrizePicks app today and use code SHANNON to get $50 in lineups after you play your first $5 lineup! https://prizepicks.onelink.me/LME0/SHANNON

Bert Kreischer sits down for a wide-ranging conversation that traces his unlikely path from Florida State party legend to sold-out arena comic. A Florida State alumn, viral content creator, and self-described one of the greatest partiers of all time, Bert reflects on how his reputation—and work ethic—eventually turned into a full-blown comedy empire.

Bert starts by talking about where the clothes Shannon Sharpe gave him ended up, then recalls running into Shannon two Super Bowls ago and admitting he was already a fan. He breaks down playing an exaggerated version of himself on stage and promotes his Netflix comedy series Free Bert, explaining how leaning into character became part of his success.

The conversation turns personal as Bert opens up about being an unsuccessful young dad while surrounded by parents who seemed to have it all together. He discusses watching his friends get rich around the same time he did, questioning what kind of millionaire he wanted to be, and dealing with an identity crisis and survivor’s remorse as fame hit while others struggled. He explains how his podcast became awkward when people kept asking how he “made it.”

Bert revisits his six-year run at Florida State, how a Rolling Stone article changed his life, and why Oprah asked to have him and his parents on her show. He explains why he stayed in college so long and how he began turning stories from his friends and daughters into stand-up material—including stealing a joke from his daughter that she later demanded he remove.

He shares stories of his daughters touring with him alongside Mark Normand, Shane Gillis, Joey Diaz, and Sal Vulcano, their no-nonsense views on celebrities, and setting boundaries like refusing to curse before 16 or asking him to delete videos. Bert also laughs about answering phone calls on stage, including picking up when Shaq called him from the toilet.

Bert talks about walking away from baseball to become a full-time party guy, the embarrassment of losing his virginity, and how National Lampoon: Van Wilder—starring Ryan Reynolds—was inspired by his life. He explains why he chose not to sue, his desire to meet Reynolds, and hopes of appearing in a future Deadpool.

The episode also covers his dad funding his move to New York, tough love birthday advice, getting fired for taking his clothes off at work, meeting Will Smith, pitching movies, and getting career advice at a urinal. Bert revisits the viral Russian Mafia train-robbery story, advice from Joe Rogan, tension with Kevin Hart, thoughts on Katt Williams, legendary comedians like Patrice O’Neal and Ralphie May, financial mistakes, marriage without a prenup, and his experience at the Netflix Tom Brady Roast—all before circling back to Free Bert on Netflix.

See omnystudio.com/listener for privacy information.