I'm Gen X and I'd rather sew my vagina shut than go near any man into Musk/Peterson/Trump/Rogan, etc, for what it's worth. Can't speak for the boomers though.
But he's also a sneako right winger. he always claims to be just asking questions but he platforms primarily people on the right, including his ghoul of a friend Alex Jones, with occasional responses from the other side, but it's heavily skewed. He's a hard r republican even in violation of his own beliefs, supporting politicians who would re-criminalize weed
Shapiro might be a smarmy queef, but at least he wears his allegiance on his sleeve, Rogan, Peterson, and Musk play coy for broader appeal like they're not fully in line with the party and they don't understand the allegation, when they absolutely are and they absolutely do. To quote one of them "I can't say I respect that"
His podcast used to be like sneakily listening to your dad and uncle shoot the shit. It would be funny, insightful, philosophical etc.
Now it's like listening to your senile grandpa bitching about the same thing over and over again telling the same story and shitting on the youth for doing the same thing he did when he was younger.
This but if your granpa is often inviting antivaxxers and transphobes over to chat and every time they say something fucked up he's just like "Ya.. totally...wow... you're right..."