“I’m worried I came off like an asshole,” Bill Burr says. “I hope I didn’t.”

Burr is standing in his trailer on the set of his feature directorial debut, the semi-autobiographical Old Dads, and looks worried. The actor-comedian is wrapping up our wide-ranging interview in which he talked about such topics as the early days of his career, cancel culture, the firing of his Mandalorian co-star Gina Carano and his controversial SNL hosting gig. It all culminated with one of Burr’s trademark impassioned monologues (don’t call it a “rant” — he has a whole not-a-rant about the hyperbolic use of that word).

In fact, even a compliment can potentially rub Burr the wrong way. “When I was younger, I would really feel uncomfortable around healthy people,” he says. “If someone was really nice, I would just be like, ‘Get away from me.’ If someone was an asshole, it’s like, ‘Oh, that seems familiar.’ For whatever reason, I don’t like being complimented.” Then Burr reverses himself for a more candid confession: “I mean, I wouldn’t be doing what I do if I didn’t want to get complimented. I have a crushing need to be liked, and what my peers think is huge to me.”

These days, if he would accept it, Burr could bask in adulation from his fans and colleagues. At 53, he is one of the few comics who can sell out arenas like Madison Square Garden and London’s Royal Albert Hall. This fall, he’ll become the first comic ever to play Fenway Park. His upcoming Netflix special, Live at Red Rocks, will mark his fifth for the streamer. Meanwhile, he continues adding to his acting credits, which include playing Pete Davidson’s would-be father figure in 2020’s The King of Staten Island. Old Dads will mark his first role as a leading man.

On the eve of the Netflix Is a Joke comedy festival, where Burr is one of the headliners, the comic sat down to chat. He looks skeptical and, every so often, is a tad combative. I made it my private goal to relax Burr enough to uncross his arms, and occasionally he would — then he’d cross them right back again. Burr has reasons to be mistrustful. The media have been making assumptions about him based on his stand-up for decades.

“You can’t take one incident or one quote and say, ‘That’s who you are,’” he says. “It took me 50 years to figure out who I am, and I’ve been with me for 50 fucking years. How are you going to figure out who I am in a joke?”

While there’s no shortage of irate white dudes doing counter-outrage humor, Burr has never been only that. His set will typically span an array of topics ranging from his childhood to sex robots to how much he loves his dog. When he does touch on a cringeworthy subject, he’s crafty enough to anticipate and toy with the crowd’s reaction. Burr will stand there, casually leaning one arm on the mike stand, a mischievous grin on his face, acting like the loud guy at a bar who knows he might be full of shit. “You know what’s hilarious about sexual assault?” he gleefully asks in his 2019 special, Paper Tiger, and you wonder: Oh God, how’s he going to get out of this one?

Burr’s mastery of the medium is the result of decades of grinding — the opposite of overnight success. And as our conversation began, he traced it all back to one day in Boston, 1992.

Burr has said he’s had nightmares about this moment: He’s a student majoring in radio at Emerson College and watching stand-up comedy on TV with a friend. His friend says that their own jokes are funnier, and suggests they attempt stand-up sometime. Burr’s nightmare is that he makes a different choice. What if he had never even tried?

The Massachusetts-born son of a nurse and a dentist grew up in what he calls “the safe suburbs.” Yet Burr’s sense of safety didn’t extend to his home life, where he says he was emotionally abused by his volatile father.

“I thought I became a comedian because I loved comedy and I liked making people laugh,” Burr says. “But I became a comedian because by the time I was 23, I was so walled-off and fucked-up that doing stand-up was the easiest way to go into a room full of strangers and make them like me so that no one would hurt me. I was onstage with the mindset of a 6-year-old from 23 to about 37.”

He tried a few odd jobs (assisting at a dentist’s office, construction, warehouse work), but stand-up “felt right.” The Boston comedy scene’s aggressive fastball delivery style influenced his own, and two years after first hitting the stage, he moved to New York City. Back then, Burr was working clean (i.e., no swearing) because he was afraid of offending the crowd and fretted about getting heckled.

His biggest inspiration was Chris Rock, who was only four years older but already a star breaking into Hollywood. So Burr focused on relentlessly improving his craft, “steering into my weaknesses,” he says. If he was bombing at a particular stand-up skill — reenacting a conversation, for instance — then that’s what he would force himself to do, failing over and over, until he could crush it.

“I don’t have to be Richard Pryor, I’m never going to be him,” he recalls thinking. “But each time I could be better than the last. And what you find is you actually have more in the tank than you think you do if you push yourself. That’s why you should never judge somebody, because you have no idea what they have. Not only that, they don’t have any idea what they have until they really push themselves.”

So Burr pushed. For years. He traveled the country. Played the clubs. Did the morning shows. He eventually became a headliner. And then … he became stuck — or at least what felt like being stuck.

Burr was 37, sleeping on a futon, scared and depressed.

“I had no manager and no booking agent,” he says. “I got unincorporated because I wasn’t making enough money. I was back to living in a walk-through in New York. The phone wasn’t ringing.”

His stage time and constant moving about the country were the only things, he says, “keeping me ahead of the smoke, the depression and the fog.

“I was going to the same cities and the same amount of people were showing up, and I was getting older,” he says. “You start thinking, ‘Wait, am I the guy who doesn’t make it?’ — which is stupid because I already did make it, I just wasn’t selling a zillion tickets. I was headlining, I was paying my rent in New York by telling jokes — that’s about as good as it gets. But I was a younger man then and didn’t know that. Also, there were other things I wanted — like being married and having kids — and I wasn’t in a place to make that happen.”

Depression became anger, and anger came out onstage. Burr’s act was volatile, and it suited him. “That was probably the angriest I’ve been, and [career struggle was the] source of my anger in my comedy back then,” he says.

Still, something needed to change, and Burr made two key decisions. First, he stopped working clean, deciding, “I’m just going to talk about what I think is funny.”

The second transformation happened after a talent agent came to one of his shows. “This agent is going, ‘He’s funny, but he’s got a weird look,’” Burr says. “I knew what that meant: ‘He’s this redheaded guy. What are we going to do with this guy?’ It was an unwritten rule: The redheaded guy did not get the girl. [My act] was this odd combination of watching Ron Howard melting down.”

Which inspired Burr to quit fighting his follicles. “There’s a pressure: Hollywood likes hair, so you’ve got to look this way or that way,” he says. “That’s when I said, ‘You know what? Fuck all of this. If I’m going, I’m going to go down swinging, and I might as well swing the way I want to.’”

Burr shaved his head and, with it, the last of any desire to conform to Hollywood expectations. “I buzzed my head and I looked like the asshole that I was,” he says. “That’s when I became OK with me. All of a sudden, I started getting cooler opportunities.”

The next several years were a flurry of long-earned breaks combined with Burr making some impressively prescient career decisions.

In 2005, he scored his first HBO stand-up special, on the series One Night Stand. But in 2012, he switched to Netflix, where he’s been ever since, boarding the streaming train years before it was considered a desirable platform.

Burr also jumped into podcasting early, launching his Monday Morning Podcast in 2007 (two years before format king Joe Rogan entered the realm). Burr’s podcast has a low-key style, with the comic, typically by himself, musing about whatever happens to be on his mind (sports, cars, cigars, family, Hollywood …). It’s always hanging around near the top of the podcast comedy charts.

His podcast, in turn, spawned the All Things Comedy network and digital studio in 2012, which he co-founded with comedian Al Madrigal and has since grown into the largest collective of comedy podcasts in the world. “Podcasting blew up and all these business guys were coming in, going, ‘I created a network. You come in and I’ll own your podcast,’” Burr says. “It’s what they do to artists — they can’t just take half, they’ll take the whole fucking thing if you let them. I and Al Madrigal were like, ‘They’re just building a website. Why don’t we build a website?’”

There were other goalposts along the way, random moments that elevated Burr a few more notches in public awareness. His 12-minute vitriolic improvised rant (a legit use of the word, in this case) against a rude and unruly Philadelphia comedy crowd in 2006 made him a legend in stand-up circles (“Rocky is your hero — the whole pride of your city is built around a fucking guy who doesn’t even exist. … Go back to the dock and unload some shit, fucking warehouse-working, weed-smoking, fucking disappointment to your mother” — and 11.5 minutes more of that).

Another viral moment came in 2017 when a Fox Good Day New York morning show host asked Burr if he went too far with making jokes about Christianity. Burr shot back: “Don’t you think the Catholic Church went a little too far?”

Says Burr’s longtime business partner Mike Bertolina, “What often dazzles me is how quickly he can take what’s going on around him and convert it into material. When the Kyle Rittenhouse trial happened, we talked about it on a trip to Vegas. He went up that night and did 20 minutes on it — and it killed. Where did that come from?”

Despite his talent, Burr is less of a celebrity figure than his ticket sales might suggest. He’s not a guy regularly hitting red carpets. Asked if he deliberately avoids some of the trappings of Hollywood, he quips, “I’ve been able to avoid a lot of them because of how I look — nobody gives a shit about a bald, redheaded male.”

Then, more sincerely, he says, “Being out and being known is loud. I don’t do well with it. There are people who are electrifying and they should be out there, and I love watching them. But I loved how the Beastie Boys would put out an album and do a tour and then disappear for a couple of years. Just as you’re thinking, ‘Hey, what happened to those guys?’ — bam, they drop another album and blow your mind again. I also think that for a comedian, the more you can have a regular life, the more a crowd can relate to you.”

Burr adds: “My wife would laugh if I said this, but I’m kind of a quiet person.”

“Yes, I do laugh at that,” replies Burr’s wife, Nia Renée Hill (and then she does). “He’s probably the loudest person I know. But I know what he means. He can be very introverted.”

Burr met the actress-writer through her father, Ben Hill, who booked comics on Showtime at the Apollo. (“The first thing I thought was: ‘Oh wow, that is a really cute redheaded guy,’” Nia says. “We connected kind of immediately.”) Their 18-year relationship has played out in Burr’s stand-up, with Nia often a comic foil for battle-of-the-sexes humor. “It’s part of being with a comedian,” she says. “You have to be comfortable about it, and if I ever felt like he was going too far with it, I would say something.”

For all Burr’s ripping on marriage (sample: “Three out of four marriages go right down the drain. If you were going skydiving and they told you three out of four parachutes weren’t going to open — ‘Forget it!’”), he positively lights up when he talks about his wife. “We are a forgiving couple,” he says. “We both have done dumb shit to each other, but at the end of the day, we know we’re not going anywhere.”

His family also inspired him to get back into therapy a few years ago to focus on his anger issues. In his upcoming Red Rocks special, Burr declares, “You wouldn’t know it from all the ignorant shit I’ve said so far, but I’m a changed person.”

It’s an oddly complicated topic, Burr’s anger. If you ask what people’s biggest misconception about him is, Burr says: “That I’m an angry guy. People think, like, I’m just walking around fuming, or they’ll watch my act and take it literally.” Nia agrees. “He has certain triggers, for sure,” she says. “But when he’s home, he’s just a goofy dad.”

At the same time, Burr admits, “I’m not going to lie. Somebody pisses me off, I’ll carry it for like three days. But now I squash shit rather than carry it [longer]. Otherwise, I’ll find myself driving down the street, having an argument with somebody from three decades ago.”

Another shift came when Burr stopped drinking alcohol in 2018. Quitting, he says, wasn’t difficult: “All I need is go about 10 days of not doing something and I can walk away from it.” What’s interesting is the moment he decided to stop.

“The dumbest thing I did was I brought booze home,” he says. “My daughter was born, and I was doing [Burr’s animated Netflix sitcom] F Is for Family. I’d come home, and after 10 hours in a writers room, your brain is fried. I’d put on the TV and watch Peter Gunn, 77 Sunset Strip, The Untouchables — these old series — and was drinking every night. There was this thing in my head going, ‘You have a little girl upstairs right now and you are shit-faced. If someone comes through that door or, God forbid, something happens and you have to take her to the hospital, you can’t.’ The weight of that bothered me.”

Burr has likewise adjusted some of his other attitudes, noting in his new special that he no longer “trashes women.” He won’t specify which old jokes he regrets, if any, but says, “Tonally, I would’ve been a little more playful.

“I like how I’m seeing the world now and I feel like I’m doing less of this (points at an imaginary person) and more of this (points at himself),” he says. “I’ve made every mistake you can make, pretty much. I’ve hurt people and I’ve helped people. At the end of the day, you want to have more good stuff on that side of the ledger than bad stuff.”

Yet it would be wrong to suggest Burr is now some stoic who pulls his punches. If anything, his blunt self-criticism has allowed him to strike harder. In 2020, he was asked to host SNL for the first time. His monologue took on the racial reckoning from a unique perspective — mocking the complacency of woke white women.

“You guys stood by us toxic white males through centuries of our crimes against humanity,” he said to nervous-sounding studio audience laughter. “You rolled around in the blood money, and occasionally when you wanted to sneak off and hook up with a Black dude, if you got caught, you said it wasn’t consensual. So why don’t you shut up, sit down next to me, and take your talking-to.”

When I suggest that he managed to “skate on the edge” of outright offense with that one, Burr quickly pushes back.

“I didn’t ‘skate on the edge’ of anything,” he says. “I said exactly what I was thinking. [White women] go after these guys going, ‘You were complicit!’ But weren’t you? Their complaining is louder than people that have it worse and it’s so goddamn hilarious to me. And that was the Disney version of those jokes. [SNL insisted] I say ‘non-consensual’ instead of ‘rape.’ Oh, you can’t say rape? That’s what white women said when they got Black guys killed. ‘You can’t say that.’ You can’t say that? Why? Who’s going to get offended and who do they listen to?”

Burr’s new special is likewise provocative (it includes his thoughts on lesbian relationships and closes with his “weird take” on abortion). I tell him that while watching it I wrote this down: “The term ‘toxic masculinity’ is one that Bill the comedian would ridicule but Bill the man has spent most of his adult life acutely aware of and trying to actively address.”

Burr just stares. “That’s a stupid statement,” he says. “You’re dragging all other men into my behavior. I am responsible for my behavior, right? If I’m acting like an asshole, I am an asshole. You don’t have to drag you into it!”

Burr sounds annoyed, but doesn’t look it. He’s leaning forward and engaged. Just as compliments make him uncomfortable, it turns out the inverse is also true: Confronting Burr can fire him up. Interviewing the man can be like playing a video game where you invert the Y-axis on the controls: Up is down, down is up, and your usual instincts are all thrown.

“I think he’s most comfortable when things are uncomfortable, and you can see it in interviews,” Bertolina says. “He’s always trying to get better, and if people treat him like he’s the best, then where does he have to go?”

Burr’s directorial debut, Old Dads, follows him as a middle-aged father who, along with his two best friends, sells the company they own to a millennial. The trio realize that they’re out of touch and must figure out how to make it through an ever-changing world. The story was inspired by Burr and co-writer Ben Tishler’s experience becoming fathers late into adulthood.

“It’s Bill’s stand-up in a narrative format,” Bertolina says. “You see this progression in him as he’s working on his own issues — most centered around his anger.”

There’s also the hypothetical possibility of Burr appearing in the upcoming final season of Better Call Saul (he played a small-time fixer in Breaking Bad) and the third season of Mandalorian (but he won’t confirm either).

“I just do stuff if it seems like it’s fun, and the people I’m working with are trying to do something great,” Burr says. “You go on the set of Mandalorian, they’re trying to make something great all day …”

He pauses, looks despondent. “That makes me think of Gina. How cool she was as a person …”

Actress and MMA fighter Gina Carano co-starred in The Mandalorian’s first two seasons, but was fired from the series — and from starring in a planned spinoff — after her posts on social media promoted Donald Trump’s debunked 2020 election fraud claims and seemingly mocked transgender pronouns. Disney apparently was tipped into ousting the actress after she compared the suppression of conservative political views to Nazi Germany.

I ask Burr if he thinks Carano’s firing was a fair move.

“No,” he says. “I thought it was funny that the liberals proved her point. They just use outrage because they don’t like your politics. As someone who considers himself liberal, it’s disappointing to see the left become how the right used to be when they went after the Dixie Chicks after they criticized George W. Bush. There’s not a lot of people like that — most are just trying not to get in trouble — but there’s this small collection of lunatics — either on the right or the left, at any given moment – that cause hysteria. And now there’s so many [media outlets] that want eyeballs, they make money off advertising, that they give attention to these crazy fringe people.

“The whole thing with Gina: You can’t chime in when the shit’s happening, because then you cause static for other people on the [show],” he adds. “That somebody’s opinion — or their political beliefs — makes people try to destroy their ability to make a living, it’s fucking bizarre to me.”

Burr is ramping up now, doing what audiences around the world pay to see.

“And I love the whole idea that somebody can go back eight years in somebody’s Twitter feed and be like, ‘What about this?’” he continues. “And nobody says, ‘You had to go back eight years to find something?! Sounds like this is a pretty good person if you had to go back eight fucking years!’ Meanwhile, there are people who get paroled from prison every day who have done so much worse and they’re allowed to put their lives back together. You can have 20-year wars, you can create synthetic heroin, you can fucking poison the food supply. You can do all of that shit and it’s barely going to read. They did a study the other day that 85 percent of people have plastic in their body – horrifying. Who’s going to be held accountable for that? Nobody. But I could tell you five different topics that if I did jokes about, I would get more in trouble than the people who caused that.”

Is Burr truly, deeply angry here? Performing? A bit of both? Harrison Ford was once asked by a reporter if his tears were real in a movie scene and he replied: “It doesn’t matter as long as you think I’m crying.” Burr might always rage against the frustrations of modern life, lashing out at things beyond his control. But underneath it all, there’s something else. He knows that, as screwed up as everything is, in some ways it’s all OK, too.

“I’ll be honest,” he says. “In 2011, I bought a house with money from being a stand-up. And I remember [being] on the back porch with my beautiful wife and said, ‘I know you’re not supposed to say this, but I made it. I’ve been satisfied for a long time. Anything I get after this is great.’ The most inner peace that I’ve had in my life is where I’m at right now.”

A version of this story first appeared in the April 27 issue of The Hollywood Reporter magazine. Click here to subscribe.