Quote · 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Fat Tommy Vs Skinny Tom | 2 Bears, 1 Cave
Where this was said
Five Apartments In Five Cities
At 36:53 · chapter starts 36:37
From the Hulk Hogan documentary, Bert pulls two insights: Hogan told stories the way he wanted you to feel, and he gradually inflated Andre the Giant's weight from 650 to 700 lbs across retellings — a pattern Bret Hart confirmed on camera. Meanwhile, Macho Man Randy Savage reportedly borrowed his 'Oh yeah' from another wrestler and eventually let the character swallow him whole, treating Miss Elizabeth in public the way she was treated on screen. This sends Bert into an unexpected moment of self-awareness: does he do the same thing with LeeAnn? He has a running joke that she's 'off leash,' and he realises he may be casting her as a character in his stories rather than reporting truth. The episode's comedic aside is LeeAnn arriving at the studio, Bert warning the crew she's off leash, and Kyle getting 'bitten' by her. Bert credits sobriety — he's 53 and only now starting to pay attention to these patterns.
Bert pitched LeeAnn a radical life reset: sell the house, buy five small apartments in five cities, and just travel. LeeAnn's five cities — Hawaii, Austin, Atlanta, New York, Chicago. Bert traded Chicago for Mexico City and added Florence. The whole fantasy started because LeeAnn admitted she wasn't happy.
