There is a running pattern with Bert Kreischer that anyone who follows the comedy podcast world has noticed by now. Every single time Shane Gillis comes up in conversation, Bert finds a way to make himself the central figure in Shane’s story. It happened again recently on Two Bears, One Cave, and it played out exactly the way it always does.
The conversation started innocuously enough. Tom Segura was talking about the response to his new Netflix season of Bad Thoughts, noting how meaningful it is when fellow comedians reach out with praise. Tom mentioned that Shane Gillis had called to tell him how much he liked the show. That is where things took a familiar turn.
Rather than simply agreeing that it was a nice gesture, Bert immediately redirected the conversation toward himself.
“I’ve known Shane longer than you have,” Bert told Tom, “and arguably I’m closer with him, and he never said a word about my TV show.”
From there, Bert spent several minutes processing his feelings about the slight in real time, eventually declaring that it bothered him so much he might have to reach out to Shane directly.
What made it funnier was the added detail that Shane had offered Bert acting tips when he was heading into production on his own show. Rather than taking that as a genuine and thoughtful gesture, Bert seemed to file it away as another entry in a growing list of grievances.
He also noted, with obvious irritation, that he never even got an offer to appear in Gillis’s project Tires, which he kept referring to as “Wheels.”
This is the formula. Bert compliments Shane, pivots to his own connection with him, and then quietly positions himself as the person who was there first, who knew him longest, and who played some foundational role in his rise. The implication is always the same: Bert discovered Shane before the rest of the world caught on.
The reason this keeps happening is not hard to understand. Shane Gillis represents something that Bert and many of his peers cannot manufacture. He built a genuinely independent career, earned credibility with mainstream audiences and hardcore comedy fans alike, and did it without needing constant validation or public positioning.
He shows up, does the work, and disappears. That combination of authenticity and success is rare, and it gives the entire Austin comedy circle a legitimacy it would not otherwise have.
For someone like Bert, who openly needs external approval and has spent years cultivating a persona built on being lovable and well-connected, watching someone younger achieve more with less effort clearly stings.
Rather than sitting with that quietly, Bert processes it out loud, on the podcast, in real time, while Tom Segura sits across from him trying not to laugh.
The episode also featured a dig at Shane that Bert seemed to think was a compliment. Comparing Shane to Justin Timberlake and other long-established entertainers, Bert remarked that Shane had barely been in the industry long enough to know what he was doing. It landed as a backhanded slight dressed up as praise.
The irony is that Shane almost certainly does not think about any of this.
