In early July the comedian and musician Tim Heidecker headlined a weeklong residency at the tiny Elysian Theater in Los Angeles. They were warm-up shows for his latest tour, a two-part “evening with” featuring his absurdist stand-up comedy followed by a musical set with his Very Good Band. “Tim Heidecker Live!” arrives at the Wilbur on July 27.
The LA run was “very strange,” he reports. With fewer than 150 seats in the room, it was “super intimate for a rock concert. I was making eye contact with every single person in the theater at some point.” And everyone was masked.
“I was nervous that it was gonna be embarrassing, but it’s cool,” he says. “You can see heads bopping or shoulders going. And then there’s good old-fashioned applause. But I do miss seeing smiles, or not-smiles.”
Inducing “not-smiles” is actually kind of a specialty for Heidecker, who has built a career out of a wall-to-wall brand of anti-comedy. Sending up the tropes of his chosen medium, he has cultivated a devoted following who often laugh in spite of themselves.
“You’re laughing and you shouldn’t be,” Heidecker says of his stand-up alter-ego, a slicked-back blowhard who acts like the audience should feel lucky to be in his presence. “A laugh’s a laugh.”
In conversation, he’s considerably more humble. At one point he apologizes for being “self-aggrandizing” after mentioning a musician friend who said of his music, “I think this is going to ruin rock shows for me for a while.”
“You’re getting so much more than you do at a rock show,” Heidecker explains. “More fun, more variety. It’s a little awkward for me to be talking to you about this, but I guess I gotta do it.”
Beginning with “Tim and Eric Awesome Show, Great Job!,” his sketch show with college buddy Eric Wareheim, which ran for three years (2007-10) as part of the Cartoon Network’s Adult Swim programming, Heidecker has built a little empire of awkward. He starred in “The Comedy” (2012), a dark indie film about the perils of armoring yourself in sarcasm. For a decade now he’s cohosted a satirical Web series called “On Cinema” with his friend Gregg Turkington (who has his own schlocky comedy alter-ego, Neil Hamburger). A couple of years ago he taped a classic bit in which he delivered his own eulogy.
As a musician Heidecker has spoofed Bob Dylan, started a scat(ological) band called the Yellow River Boys and, in 2017, released an album of songs roasting the Trump presidency. His latest album, “High School,” is surprisingly sincere, almost wistful, inspired in part by the death of a friend from his teenage years. (Heidecker is 46, a dad with two young children.)
“What did we do with our time?” he sings on the track of the same name. “How did we kill all of the hours?” It’s not a lament for those lost hours, but for the days when aimlessness was a privilege.
The Very Good Band features drummer Josh Adams, bassist Eliana Athayde, and guitarist-pedal steel player Catfish Connor. “They’re so good, but they also come from that school of the Band — ‘70s rock, good vibes, they don’t play too loud, they’ve got good taste.”
So the band name is “right on the money,” he says. “Also, what am I gonna call it — Tim Heidecker and the Raconteurs? Tim Heidecker and the Dusty Stains? Names are kind of silly anyway, let’s just be honest.”
In recent years Heidecker has begun to let down his guard, giving fans occasional glimpses behind the personae.
“My audience, the people likely to come see me, we’re not fully aligned on everything, but I think we have a general, baseline set of values and beliefs. I’m not worried that I’m gonna get heckled for saying basic things.
“Last night, I said, ‘How’s everybody doing? And I don’t mean right now, I mean in general.’ ” The collective response was predictably glum, he says.
“We’re all a little unmoored.”
As a result, recent audiences have been out ahead of him, eager to laugh. “They’re almost too enthusiastic for the bad stuff,” he says with a laugh.
For years, he says, he couldn’t quite articulate his own arch style of comedy.
“It was hard to talk about, or even for me to understand what we were doing, and why it connected,” he says. As students at Temple University, he and Wareheim rented videocassettes of Andy Kaufman’s comedy sketches.
“We were obsessed with those, especially his talk show, with the giant desk,” Heidecker recalls.
Then he read Steve Martin’s book “Born Standing Up: A Comic’s Life.”
“That moment when he explains his own epiphany about what he was trying to do, I just identified with that right away,” Heidecker recalls. “It helped me understand, oh yeah, it’s not about the punchline — it’s just creating the entire vibe to be funny. There’s this rolling laughter of confusion, ‘this is so stupid.’ It doesn’t start and stop. It just flows.”
It takes patience and a certain amount of fortitude to work that way for laughs.
“There are always moments in the set when there’s no laughter, and there might be one guy just losing it,” Heidecker says. “And it takes a minute for it to roll through.”
But if you can ride it out, the laughter always comes.
TIM HEIDECKER LIVE!
At the Wilbur, 246 Tremont St. July 27 at 7 p.m. $41.50-$101.50. thewilbur.com
James Sullivan can be reached at email@example.com. Follow him on Twitter @sullivanjames.