What does a contrarian, grievance-happy comedian do when contrarianism and grievance become the norm? Bill Burr, long the poster child for a type of angry white male misanthrope, may be the last person you’d expect to embrace empathy in response to, well, everything — but that seems to be the case.

Burr recently told NPR’s Terry Gross that “there’s also a part of me that really hates the fact that I have been so angry.” His new Hulu comedy special, Bill Burr: Drop Dead Years, leans all the way into that remorse, with jokes that — for the most part — sidestep giving into anger and remonstrance in favor of self-reflection. It’s a far cry from his old persona, which often reveled in jokes about lesbians, fat people, trans athletes, and other marginalized groups who seemed to draw his ire.

Burr discusses things that he previously would likely have been the first to ridicule: his experiences with therapy, learning how to be a kinder partner, and the real effects of toxic masculinity on men. He even opens up briefly about experiencing intense depression and childhood sexual abuse. It’s pretty weighty stuff, treated with surprising and studious care.

Alongside the special, he’s also making headlines for taking aim at billionaires, defending Luigi Mangione, getting into fights with conservative commentators, and roasting Elon Musk for doing a Nazi salute — a move that he claims got him flagged by the Musk-owned X. It’s leading some conservatives to ask, is Burr actually “going woke?”

Well, no, not exactly. But there is something new to the way Burr is positioning himself as a man in 2025 America. “He is giving voice to a feeling that the rules or acceptable strategies for climbing the masculinity ladder feel opaque,........

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