In this candid, hilarious, and unexpectedly moving episode of On Purpose, Jay sits down with comedian, actor, and podcast superstar Bert Kreischer—famously known for his shirtless stand-up and his ability to keep audiences laughing nonstop.
This conversation goes way beyond the jokes as Jay and Bert dive deep into the real stories behind the spotlight, revealing the layers of vulnerability, self-doubt, and emotional growth that make Bert more than just a party-loving comic. Bert shares what it was like growing up with a tough, old-school dad who believed in powering through pain and never showing weakness.
That mentality helped shape Bert’s work ethic but also left him carrying emotional weight for years. In one of the most touching moments of the episode, Bert shares how a simple, unexpected conversation with his dad, while they were both high on edibles, changed everything, helping them finally see each other clearly and connect on a deeper level. With Jay’s thoughtful guidance, they unpack Bert’s real-life struggles with anxiety, chasing approval, and feeling like you’re never enough, things so many of us can relate to.
Bert is refreshingly honest about his mental health, his parenting ups and downs, and what it’s like trying to stay grounded while raising two sharp, hilarious daughters who aren’t afraid to call him out.
Bert Kreischer: Bert Kreischer is a stand-up comedian who performs to sellout crowds across the country. His latest stand-up special, Bert Kreischer: The Machine, premiered on Showtime. He is the host of the Travel Channel’s Trip Flip and Bert the Conqueror and previously hosted Hurt Bert. He is a regular guest on The Joe Rogan Experience and The Rachael Ray Show and has appeared on Late Night With David Letterman and Jimmy Kimmel Live. His previous one-hour special Comfortably Dumb appeared on Comedy Central and his book Life of the Party, Stories of a Perpetual Man-Child shares the hilarious and outrageous stories that define his comedy and exemplify what has made him one of the best story-tellers of his generation.
