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 youd expect to embrace empathy in response to, well, everything but that seems to be the case.Burr recently told NPRs Terry Gross that theres 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. Its 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. Its pretty weighty stuff, treated with surprising and studious care.Alongside the special, hes 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. Its 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, contradictory, and changing, Northwestern sociologist Rebecca Ewert told Vox, referring to the status hierarchies men have to navigate in a patriarchal society. There have been rules they have never been consistent. Black men need different strategies than white men. There are different ways of proving dominance in a weightlifting gym than on the floor of Congress. Burr is explaining that they feel more contradictory than ever.As a 56-year-old white guy, Burr embodies the much-discussed masculinity crisis yet while griping about his losses, hes also noticing that even his advantages can be shortcomings in disguise. Hes articulating ways the system doesnt serve him, Ewert said, but hes also so afraid to lose that system hes been seeing his whole life. And were seeing that throughout the culture.You might think that anxiety over his perceived loss of status would produce even angrier comedy. Yet counter to prevailing cultural narratives about angry white men getting older and more cantankerous, Burr seems to feel liberated by aging. Hes happy to be getting along better with his wife, relieved to finally be able to say out loud that hes sad. Men arent allowed to be sad, he says, in a self-deprecating moment describing how he opened up to his wife about experiencing emotion. Were allowed to be one of two things. Were allowed to be mad or fine. Its far from an earth-shattering revelation, but it feels significant when its coming from someone like Burr, who previously seemed defiant and even proud of his limited emotional range. He was far from alone; if anything, he was part of a cultural moment that seems geared toward rewarding emotional repression and regressive forms of masculinity. University of Birmingham sociologist Yuchen Yang points out that Burrs sudden interest in chilling out is self-serving on an existential level. He has for many years served as the poster child for a kind of masculinity that, as Yang put it, is not only harmful to women, queer, and people of color, but also detrimental to [men]s own existence.Dominant cultural beliefs about manhood often lead men into an unhealthy lifestyle, Yang said. Yet at the same time, the stigma around vulnerability also makes it difficult for men to seek help when needed, he explains, pointing to therapy, medical invention, and simple wellness tactics as preferable alternatives to doubling down.The real issue, Yang says, is that men are chasing a cultural ideal that is far from realistic. As he points out, Very few men can actually achieve this ideal, and those who do get close to it can hardly embody it all the time. In other words, even as men want to embody a patriarchal masculinity, theyre just as trapped by its societal expectations as everyone else. Over the last decade, the manosphere internet spaces focused on the lives and status of men, dominated by influencers and podcasters like Andrew Tate, Joe Rogan, and a coterie of their peers emerged as both a reaction to and worsening agent for this problem. Yang suggests its existence is an attempt to resolve the inherent contradictions of patriarchy without overthrowing patriarchy. Those in the manosphere want to recover mens natural masculinity, he said, but there is nothing natural about the kind of masculinity they are invested in.While these online spaces give men a sense of community, they also foster growing misogyny, extremism, and disgruntlement. Men now are more isolated than ever, and compared to women, theyre dying younger and are more likely to die by causes including suicide, overdose, or complications from alcohol or drug abuse. Throughout Drop Dead Years, Burr discusses his own struggle with alcohol addiction as well as the broader epidemic of sad men. (The number one place to see sad men? he jokes. Guitar Center.) Yet he seems to have not only recognized all of this, but decided to evolve in response. Burr makes the point that all of that repression of emotion takes a real toll on mens health notable in a special that references his awareness of dying throughout. You start thinking about your life, you know? he confesses. You take stock in it. I start thinking about how fast my lifes going by, how quick my kids are growing up. None of this is quite as simple as man realizes he wants to be a better person as he gets older. What stands out to Ewert is his deep ambivalence about all of this. She notes that Burr often swings from serious discussion about his deepest fears and hopes to jabs about women as if his gut reaction is to punch down in order to remind himself and others that hes not on the bottom.I dont see him making a coherent argument. I see a lot of reactions, she says. Thats relatable I think thats what a lot of men are going through.Theres a sense that Burr has been working out not only how to get in touch with his softer emotions, but how to do softer, less confrontational comedy in a way that still feels nuanced comedy that we might think of as punching sideways instead of either of the expected directions. At one point, he roasts his audience members for laughing at a joke he sets up about Joe Biden and dementia. Not 30 seconds ago, when I said someone in my family got diagnosed [with dementia], you guys were all you could hear a pin drop. And you had empathy, he points out. Second you put a blue or a red tie on it Fuck that old man! Fuck him! Im glad hes gonna die! In recent years, comedy has been treated to a litany of comics, from Dave Chappelle to Louis C.K., who, when called out for various offenses, have doubled down on their commitment to disgruntlement. Burr, too, isnt over the idea; hes still frustrated that the rules about who gets canceled and who doesnt are so inconsistent, still talking about how the social phenomenon has rendered him unable to insult someone who deserves it. Even if he took my last slice of pizza and is denying it with pepperoni on his breath, Burr says, I cant be like, You fat, man-titted c**t. But whatever Bill Burr might say about cancel culture as a corrective, in his case, hes managed to do the one thing that the liberal backlash was seeking all along: listening and trying to be a little better. Its the thing that none of those other comics got around to.I think he has been seeing the real rewards of emotional connection in his life, Ewert said. Yelling on stage is one thing, she notes, but at your house you realize that not yelling makes you feel better. I think theres hope in this message, she continued. If more of us could talk about mens issues, about mens mental health, as the result of a patriarchal system that puts all of us in a hierarchy, then that helps all of us.See More: