Custom shirt because no store stocked his size
Bert Kreischer had shirts custom-made because he was too large to buy one off the rack from any store.
Snapshot · 2 Bears, 1 Cave with Tom Segura & Bert Kreischer
Fat Tommy Vs Skinny Tom | 2 Bears, 1 Cave
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Jul 27, 2026
Where this was said
Fat Tommy Vs Skinny Tom
At 2:18 · chapter starts 0:52
Tom opens this chapter with a striking confession: when he was at his heaviest, he had zero body insecurities. [1] — Tom Segura "Tom Segura says he had zero body insecurities at his heaviest. He only started questioning it when he looked back at photos and thought, 'W…" 02:18 He only started looking at old photos and thinking 'why didn't anyone say anything?' after he'd already lost the weight. He credits reading a Lindy West article on body positivity — in 'the gayest way possible,' he admits — with helping him accept himself as fat. Bert, by contrast, leaned into fat earlier but eventually hated it, and he draws the key distinction: Tom's fat was visceral, crammed hard around his organs, while Bert's was the softer 'sit different' variety — the kind where your legs spread and stairs are a threat. Tom says he actually liked having a hard belly; strangers would poke it and be amazed. Bert recalls having shirts custom-made because no store stocked his size, and Tom explains the weight-loss lip-injection illusion: face fat makes lips look smaller, so when it disappears, your actual lips appear bigger. The chapter closes with Bert recounting Ralphie May spotting him at a radio station and warning 'You're going to lose your whole act,' a dig neither man has ever fully forgotten.
Fat Tommy Had Zero Insecurities
Tom Segura says he had zero body insecurities at his heaviest. He only started questioning it when he looked back at photos and thought, 'Why didn't anyone say anything?' The disconnect between living happily in a fat body and the shock of hindsight is genuinely surprising.
Zero body insecurities at peak weight
Tom Segura says he never had insecurities about his body when he was at his heaviest, and only looked back at photos later and thought 'whoa, why didn't anyone say anything?'
Lips appear bigger after weight loss
Bert Kreischer explains that people assumed he had lip injections after losing weight, when in reality his lips just looked bigger once his face fat shrank.
Hard Fat vs. Soft Fat: The Two Bears Theory
Tom had hard, rock-solid visceral fat crammed around his organs. Bert had the softer, 'sit different' variety. Tom says he actually preferred his hard belly — people would poke it and say it felt like a rock. The distinction is funny, but visceral fat is the kind that presses on your heart.
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