The Art of Letting Go

On Bill Burr's 'Drop Dead Years'

Bill Burr performs in Universal City, California, 2011, Photograph, via Getty Images

“I have been on the road for the last five months . . . really thinking the worst of people.”

This is how comedian Bill Burr opens his 2010 stand-up special Let It Go, right before he launches into a tirade detailing his disgust for the human biomass he regularly encounters at the airport. It’s a sentiment you’d expect from a comedian who is known first and foremost for his anger. But contrast that with how he opens his most recent stand-up special, 2025’s Drop Dead Years:

“It’s kind of a weird thing to be over fifty, really starting to realize how fucked up you are. I thought I did stand-up because I loved comedy. I did stand-up because that was the easiest way to walk into a room full of a bunch of people that I didn’t know and make everybody like me.”

Not only is the message different, with Burr focused on his own faults rather than the faults of others, but so is the setting it’s delivered in. He’s not on stage when he says this. Instead, he’s leaning up against a wall outside the venue, speaking straight into the camera. The framing resembles a reality TV confessional. It’s only once he gets this insight off his chest that he’s able to go out and start telling jokes.

What happened in the intervening fifteen years that brought Burr to this conclusion? What made him turn inward and realize that he, not other people, was the main source of his problems? The answer lies in the long arc of his stand-up material. On the surface, his jokes may seem to be nothing more than a litany of complaints. But dig a little deeper and you’ll see one man’s ongoing attempt to confront, control and reckon with his anger.

Burr has been one of the preeminent comedians of what’s been called “The Second Comedy Boom,” typically marked as beginning around 2009 and lasting far longer than its predecessor in the 80s. He’s delivered eight one-hour comedy specials across multiple platforms, hosts an incredibly popular podcast, has acted in premier TV shows such as Breaking Bad and The Mandalorian, and was the first comedian to ever perform in Boston’s hallowed Fenway Park. All the while, he’s been known for his propulsive, vitriolic stage presence, dropping nonstop expletives while ranting about the problems he encounters in everyday life and society at large.

His first two stand-up specials, 2008’s Why Do I Do This? and the aforementioned Let It Go, certainly fit this bill. He goes on profane diatribes against Oprah, self-serve checkout lines, corporate greed, and weekend trips to the farmers market. They’re laugh-out-loud funny the entire way through, but Burr’s finger is always pointed away from himself during these specials. The problems are out there, the fault of some nebulous other, never the guy yelling while holding a microphone. He acknowledges his anger on occasion, but he mostly seems resigned to it, believing it to be an unchangeable part of his personality.

Burr’s perspective starts to shift in his 2012 special You People Are All the Same. For the first time, he realizes his anger has a direct impact on the people around him. Or, more accurately, it has a direct impact on his dog. He sees that the violent outbursts of his pit bull are the result of her emulating his intense and fiery energy. Because he moves through the world a certain way, the dog follows suit, and Burr has to deal with the consequences. No real solution is offered at the end of this bit, but the acknowledgment is a significant first step.

His next few specials follow a similar pattern. Burr is aware of his anger, he sees its negative consequences, he tries to work on it, but no meaningful progress is ever made. He’s like Sisyphus, pushing the boulder with all of his might, only for it to wind up back at the bottom of the hill. In 2014’s I’m Sorry You Feel That Way, he’s worried about having children because of how his temper might impact them. Flash forward to 2019’s Paper Tiger, he’s a first-time father trying (and failing) to control his temper around his young daughter. The theoretical has become the real, but no major changes have occurred. In fact, he closes that special by detailing how he refused to cry when he and his wife had to give their dog away. Instead, he bottled up his feelings and “added it to the shelf of anger that sits in every man’s chest.” Afterwards, he couldn’t help but wonder, “Who that I love in my life is going to pay for that in the future?”

I remember watching Paper Tiger and thinking, “Man, when is this guy going to get it together?” I had been following him for years, and aside from being a fan of his comedy, I was rooting for him. While he was as funny as ever, he seemed to be spinning his wheels emotionally, unable to access a deeper truth that was dying to get out. Luckily, the catharsis he was seeking was not far off, and it would change everything for him.

The true turning point occurs in 2022’s Live at Red Rocks. Burr details a psychedelic experience he had while on mushrooms and how it helped him come to terms with his inner demons. He didn’t feel a sense of bliss or peace while on drugs though. In fact, quite the opposite. It was a bad trip, but it had positive consequences.

As the mushrooms started to take effect, Burr was overcome by, “This profound sense of loneliness and not feeling loved.” He laid in bed, freaking out, trying to figure out what this feeling was, until it finally dawned on him.

“Oh, I know what this is . . . . This is how I felt growing up!!”

He then dives into his emotionally turbulent childhood, a subject he’s discussed on stage before. Only now he looks at it in a new light. For the first time, he acknowledges how damaging it actually was, both in the short- and long-term. There’s a clear and obvious connection between what he experienced in his early years and the way he acts now. He sees his frightened childhood self in his daughter’s tears after he yells about an unexpected Zoom call, not realizing she was in the room. It’s then and there that he vows to not make the same mistakes his father made with him when he was growing up. He doesn’t want his kids to end up like him.

Which finally brings us to Drop Dead Years, named after the time in a man’s life where he might just drop dead out of nowhere, presumably from decades of suppressing his emotions. How do we find Burr after his grand realization just a few years prior? The answer is similar in tone, but very, very different in subject.

The same comedian we know and love is still there. He curses, he yells, he gets riled up. But he’s now quicker to acknowledge his own shortcomings. He opens the special with an extended bit about being more agreeable with his wife, and identifies himself as a significant source of their marital discord. “She agreed to spend her life with me and I’m being this curmudgeonly asshole. And I’m kind of ruining the one life she has.”

More importantly, we hear a word from Burr that hasn’t come up once in his seven previous specials: sadness. After claiming that men are only allowed to feel two emotions (“mad” or “fine”), he describes in vivid detail his own sadness and how he copes with it: by ignoring it or burying himself in useless hobbies.

This, to me, is the most revealing part of the special. Obviously, his sadness didn’t pop up out of nowhere. It’s been with him the entire time. His habitual anger is just how he covered it up, because anger is a preferable alternative. It makes me think of a line from Toni Morrison’s The Bluest Eye:

“Anger is better. There is a sense of being in anger. A reality and presence. An awareness of worth. It is a lovely surging.”

It’s easier, and more fun, to be angry than it is to be sad. And Morrison is right about anger: it does involve an awareness of worth. When you’re angry, you’re saying, “I deserve better than this.” You validate yourself. Burr has gotten a lot of laughs out of his anger, but it’s not the primary emotion that underlies his explosive reactions. Once you get to that primary emotion, to the sadness that sits at the core, anger stops being so fun. You see it for what it really is — a defense mechanism.

Think about the growth, the years of serious introspection, it took for Burr to evolve from the comic of his early specials to the one we see today. That he came to this realization in his fifties makes it even more impressive. The older we get, the more entrenched our patterns become, and the harder it is to change. Making such a drastic pivot on the back nine of his life required Burr to admit he’d been living and thinking the wrong way for decades. That takes a level of bravery and courage most people do not have in them. He might not have found it at all if not for stand-up, if he hadn’t been confronting these issues night after night, year after year.

As a fan, and as someone who performed stand-up comedy for fifteen years, Burr’s trajectory captures what I love most about the art form. His specials contain a clear through line, a cohesive narrative arc. We’re introduced to the core issue in his early work, watch him struggle to resolve it over the next several specials, and witness the emotional climax during his mushroom trip in Live at Red Rocks. It all culminates with the denouement of Drop Dead Years. Both Burr and the audience finally see it all so clearly: his anger and comedic proficiency, the two things he’s made his name off of, are masking the sadness that lies at the heart of the man onstage.

I can’t think of a modern comedian who has presented an entire 360-degree view of themselves in their specials the way that Burr has. On top of that, he never stops being funny. Never once does he veer into preachy territory, or make his set feel like a monologue. Not many comedians can pull off the rare combination of being both funny and genuinely revealing. For most, it’s a trade off. I love Dave Chapelle, but I’ve just about had enough of his persecution complex over his last few specials. Why does he feel the need to keep poking the bear when he’s already so beloved and most people are on his side? Louis C.K. remains one of my favorite comedians of all time, but I really wanted to hear why he felt compelled to masturbate in front of those women. If anyone could dissect that situation with humor and grace, it’s Louis. Sure, every performer is entitled to draw boundaries at what they want to share, but as a fan you always feel a sense of disappointment when something’s been left on the table.

I wish more comedians took Burr’s route. Comedians in general have a weird relationship with what they call “honesty.” It’s a word that gets thrown around a lot in comedy, but it’s not always authentically practiced. Comics will talk about their sexual exploits, drunken misadventures, mental health issues, etc., and claim that they’re being honest. But genuine honesty requires genuine risk. An audience expects comics to talk about those topics. Comedians are supposed to be the sad clowns whose lives are falling apart. When a comic delivers what the audience expects, there’s no real risk of rejection. Contrast that with John Mulaney, in his latest special Baby J, telling the audience how disappointed he was that nobody in his rehab center recognized him. The main point isn’t his drug use, it’s the personal defects that led to him using drugs in the first place. That is a level of honesty that doesn’t make a comedian seem cool or exciting or fun to hang out with. It’s just disgusting vanity, laid bare for all to see.

I also wish audiences demanded more from their performers. Comedy fans can be annoying in the way they revel in the inadequacies of their heroes. They cheer on the personal failings of their favorites to make themselves feel better about their own shortcomings. In turn, the comedians become victims of an odd sort of audience capture where they don’t want to mess with what brought them to the dance. If Bert Kreischer ever puts a shirt on again, it’ll be a miracle. It’s stagnant performer and audience dynamics like this that lead to comedians winding up dead in some random hotel room in New Jersey. The myth of the tortured artist is a hard one for comics to break out of once they’re fully caught up in it.

Burr goes the opposite route. He makes fun of fans who don’t want him to change. During Red Rocks, when Burr mentions that he’s a changed man, an audience member cries out “Bullshit!” To which Burr quickly replies, “Are you saying ‘bullshit’ because you don’t believe me, or because you don’t want me to leave?” He doesn’t want to be someone’s excuse for why they didn’t better themselves and grow up.

This is what makes Burr a truly transcendent comedian. He’s willing to confront things other comedians refuse to confront. He wants growth. He wants change. He wants to become a better person, for both himself and for his family. And he trusts that by becoming a better person, he will ultimately become a better comic. We need more artists like him to light a path for the rest of us to follow.

Peter James is a former stand-up comic living in New York City. He currently writes the Substack Diary of a Failed Comedian.