Bill Burr figures he started building his audience in fourth grade. Back then, he wasn’t thinking Netflix specials recorded at venues like Red Rocks and Royal Albert Hall, or becoming the first comedian, on Sunday, to headline Fenway Park. Stand-up comedy was still several years in his future.
No, in fourth grade he was just a kid at Lieutenant Peter M. Hansen School in Canton trying to entertain a couple of friends. “I was making them laugh because that’s what I always did to connect with people,” says Burr, speaking from his Los Angeles home. “Then other kids saw them laughing and then more kids would come over and wanted to listen.”
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An insecure kid, Burr wanted to stop when people started gathering. But his friends wouldn’t let him. “I got it to the point where I had like all the boys in the class listening to [this] crazy story. And I just feel like my comedy career was that same thing; it started off with, like, two people.”
Burr’s days of playing to small audiences are long gone. He regularly sells out theaters and arenas, has nine specials on Amazon and Netflix, the latest of which, “Live at Red Rocks,” was released in July, and he hosted “Saturday Night Live” in 2020. The Fenway show could put him in front of nearly 38,000 fans at once, topping the roughly 20,000 who saw him during his then-record string of 19 sold-out shows at the Wilbur Theatre in 2015.
He has acting roles in shows ranging from the “Star Wars” action fantasy “The Mandalorian” to the indie sitcom “Reservation Dogs,” and he’s been nominated for an Emmy for the Roku Channel’s “Immoral Compass.” He’s also making his feature-film directing debut with “Old Dads,” in post-production now, which he also stars in.
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But every time Burr leveled up, he felt pressure that maybe he wasn’t quite ready, like the first time he was the featured comic at a stand-up show. “I remember being in my head, like, the crowd’s gonna know that I’m just good enough to do this, and they’re going to eat me alive.”
No one watching Burr’s stand-up these days would detect a lack of confidence. His comedy can be both bracing and abrasive — he ends his “Red Rocks” special with a bit on abortion, how he’s for a woman’s right to choose but still thinks abortion is killing a baby. He critiques feminism by questioning low attendance at WNBA games. He’s often loud and not afraid to throw back at hecklers, as he did in Philadelphia in 2006, when he insulted the city’s landmarks and told the crowd he’d laugh at their funerals.
There is something especially sweet to Burr about making a crowd wonder: Why the hell would you say that? But he’s always smiling when he shouts. And he doesn’t want to lead a rally — on the “Red Rocks” special, after he told the crowd he supported abortion rights, he responded to the cheers by warning them there was some strange logic coming. He has passionate opinions and wants to take the audience for a ride, but mostly, he wants to make them laugh.
“I just don’t want any level of importance put on what I’m saying,” he says. “I just want to make you laugh. That’s all I’m trying to do. And I’m an incredibly flawed human being, so take everything I say with a grain of salt, don’t take any of it seriously. And just have a good time. It’s just silly.”
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There is still a part of Burr that makes him question himself when he lands something big, like the Fenway show. At least until he hits the stage. “You go through impostor syndrome,” he says. “Why is this happening? This makes no sense. I’m going to be a fraud, found out — you go through all of that stuff. And then you go out there, and it’s great.”
Boston comedy, Boston friends
In January 1992, while a student at Emerson College, Burr made a New Year’s resolution to try comedy. By March, he’d won a competition among Boston college students and worked up the courage to dive into the local scene.
Tony V, who will open the Fenway show, remembers driving to a college gig in Maine with a young Bill Burr some 30 years ago. “He went up in front of me and had a really strong set,” Tony V says. “Then he started picking my brain afterwards, and I go, ‘Oh, this guy really gets it.’” Tony V likes to pay attention when he finds a comic who has heart, and Burr fit the bill. “Here’s a guy who likes the art as much as I do,” he says.
Burr says he used to be a nervous wreck onstage before watching Tony V. He noticed the other comic didn’t write his material down, and when he asked him about it, Tony V told him if you forget a joke, it’s time to stop doing it. That helped Burr realize he could let loose. “Tony V is the difference between trying to hit the ball and trying to hit a home run,” says Burr. “He had that relaxed swing, so the ball would just fly off his bat to the seats.”
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Frequenting clubs like Dick Doherty’s Beantown Comedy Vault and Nick’s Comedy Stop, Burr fell in with a class of comics with Patrice O’Neal, Dane Cook, and Robert Kelly, all of whom eventually moved on from Boston to find success in New York and Los Angeles. Burr made regular appearances on “Tough Crowd with Colin Quinn” on TV and the “Opie & Anthony Show” on satellite radio, places where he could be himself. Meanwhile he worked his way up from clubs to theaters — and now to Fenway.
“With each level I’ve gone to, I’ve always had to go through an adjustment period of trying to get comfortable,” he says. “And doing what I’m doing now is definitely . . . I don’t even know how to describe it, it’s just . . . it’s fun.”
At Burr’s level of fame, he doesn’t have to convince people he knows what he’s doing. That’s why he does drop-in sets in smaller settings, like the one at a comedy night at Capo Restaurant & Supper Club in South Boston in April. Alongside other comics, Burr performed an unannounced set to work on new material.
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“I was sort of in a weird headspace,” he says. “A lot of people there didn’t know who I was, so I was back to, I had to get them. And I hadn’t experienced that in a minute. And it threw me off a little bit. And then I started with the wrong thing. It was just one of those things that just, it never stops happening.”
One of the up-and-comers on the bill that night was Drew Dunn, who grew up quoting Burr’s jokes with his friends. Validation from a comedy hero can be a giant boost for comics starting out, and Dunn was inspired to see Burr struggle a bit in a smaller room. “He gave me a fist bump and said, ‘Really [expletive] funny dude, seriously.’ So yeah, that’ll stay in my head for a while.”
Bill Burr, happy?
“You wouldn’t know it from all the ignorant [stuff] I’ve said so far, but I am a changed person, believe it or not.” Burr says this in his new Netflix special, “Live at Red Rocks.” It draws an interesting reaction from the crowd — some of them boo. They don’t want Burr to change, they want him to stay angry.
Now married with two kids, Burr, 54, has no interest in inflicting his anger on his family. He has struggled with that for years, even dealt with it in his animated “F Is for Family” series on Netflix, but an experience taking hallucinogenic mushrooms for the first (and, he notes, last) time in 2021 opened his eyes. In the bit, Burr described his childhood as a combination of “The Brady Bunch” and “Lord of the Flies,” oddly functional but with lasting damage.
The mushroom trip made him feel profoundly unloved and lonely, and he realized carrying his trauma around for years had led to bad behavior. “I knew every [expletive] thing I did, good and bad, in that moment,” he says in the special.
After three decades of analyzing himself onstage, Burr finally faced some difficult truths. “It was amazing,” he says, “but it was pretty shocking to finally meet yourself in your early 50s.”
With a clear agenda of how to work on himself, he’s happier than he’s ever been, and, he says, a better comedian. “If you become happy, it adds a whole other level and depth to your comedy,” he says. “I guess if I didn’t examine myself, I would still be screaming and finger-pointing about every subject, rather than turning it back on myself to see how I fit into the whole, whatever I’m talking about.”
In one potentially heavy moment in “Red Rocks,” Burr talks about trying not to lose his temper in front of his kids. He was yelling into the phone when his 2½-year-old daughter came to him and apologized, thinking it was her fault he was angry. Burr was stunned. “Is she gonna go play with a toy and forget about it,” he says, “or is she no longer going to be an astronaut?”
But Burr doesn’t pause to let that moment sink in. His imperative is to keep the laughs coming.
“They’re laughing because they’ve done it, too,” he says later. “Anybody who’s a parent has done that. It’s cathartic to know that I don’t have to be perfect. I can’t sit here and beat myself up because every moment of my kid’s life, I wasn’t the perfect parent.”
Perfect was never the goal. Burr’s star keeps rising, but he’s been satisfied with the work for a long time. “I think I’m where I want to be,” he says. “I don’t want to be the biggest thing in the frickin world. My thing has never been that, it’s never been ticket sales. It’s always been quality and then respect from my peers. I wanted to be a comedian that other comedians thought was good.”
Nick A. Zaino III can be reached at nick@nickzaino.com.
BILL BURR
At Fenway Park. Aug. 21 at 7 p.m. www.mlb.com/redsox/tickets/concerts/bill-burr