Josh Gondelman in his comedy special, "People Pleaser."
Josh Gondelman in his comedy special, "People Pleaser."

‘Nice guy’ comedian Josh Gondelman brings shtick to S.F. on Friday

Stand-up comedian Josh Gondelman possesses the mild-mannered, sweater-vest vibe of the preschool teacher he once was — a hipster Mister Rogers, as he puts it.

That bespectacled, slightly nerdy persona has served him well in his career: He was part of an award-winning writing team at “Last Week Tonight with John Oliver,” the brainy news satire show on HBO. He’s also written humor essays for the New Yorker, the New York Times and Esquire, and he co-wrote “You Blew It!”, a 2015 book subtitled “An Awkward Look at the Many Ways in Which You’ve Already Ruined Your Life.” His first stand-up special, “People Pleaser,” was released in June.

On Nov. 4, he’s headlining at Cobb’s Comedy Club in San Francisco. A stand-up since age 19, he’s been on the comedy club circuit since 2004, so he’s definitely familiar with San Francisco.

“I love it,” said the 37-year-old Boston native. “It’s one of my favorite places to come back to. The audiences are really on top of things and smart.”

In an interview from his New York home, Gondelman said keeping his fingers in assorted comedy pies makes life interesting.

“It stops me from getting burned out from any one thing,” he said. “I was at ‘Last Week Tonight’ when I wrote my book, and it was fun having that balance. I thought, ‘This is the thing that feeds my monstrous ego.’ The book was in my voice.”

So are the topics in his stand-up act, which span from married life to his in-laws (including two brothers-in-law who are cops) to his doughy physique. He does a bit on the word “physique,” a term he thinks doesn’t really apply to him.

Also, and more than just a little, Gondelman talks about being Jewish, even more so when he plays to Jewish audiences at JCCs and Chinese restaurants — for Christmas shows, of course.

“The audiences are often older and there’s a feeling of ‘Thank goodness he isn’t my son or grandson,’” he said, referring to his occasionally racy material. “I like doing those shows. There’s a level of shared cultural understanding where you don’t have to explain much.”

That cultural understanding began in his hometown of Stoneham, Mannachusetts, a northern suburb of Boston. His father hailed from Newton, which has a sizable Jewish population. “I am of the first-generation Newton diaspora,” he quipped.

He grew up celebrating Jewish holidays, attending religious school and attempting to learn Biblical Hebrew. He recalled seeing sections in the back of the prayerbook that referred to the Holocaust, offering prayers and other readings to remember the murdjered millions. “You don’t get that in the New Testament, [a reference] to the worst thing in your grandparents’ lifetime,” he said. “That makes it feel like a thread from the past into the present.”

His comedy education began with the 1974 movie “Blazing Saddles” and Mel Brooks’ classic 2000 Year Old Man bit with Carl Reiner. He gobbled up  ‘Seinfeld,” which premiered in 1989 when he was 4½. He loved the show, but his parents were irked by how unlikeable the characters were. (He would go on to launch the now-defunct Modern Seinfeld Twitter account, imagining how the show’s characters would navigate contemporary social situations.)

He also stole away to the woods with friends to listen to Adam Sandler CDs, keeping things on the down-low out of fear of having the raunch-laden albums confiscated by his parents.

After graduating from Brandeis University in 2007, Gondelman taught preschool and grade-school Spanish. He had been doing stand-up since age 19, and he continued to grind, performing at numerous comedy festivals and clubs. He put out his first CD (“Everything’s the Best”) in 2011, made his late-night debut on “Conan” in 2016 and worked five years on “Last Week Tonight.” In one year as a web producer and four years as a staff writer, he was part of a team that won four Emmys for outstanding writing for a variety series and two Peabody Awards.

Most recently, he was head writer and executive producer for “Desus & Mero,” a comedy talk show on Showtime.

That these are disturbing times in our nation, and for Jewish comedians, as well, is not lost on Gondelman.

He knows what happened in October to comedian Ariel Elias, who was performing on stage when a heckler threw a can of beer at her and dissed her as a liberal Jewish Democrat. She promptly chugged the beer in defiance, and the video went viral. And then there’s Dinah Leffert, who announced a few weeks ago she was quitting comedy, stating in a farewell Instagram post, “Everyone [in stand-up] feels welcome except the Jews that literally helped build this craft and these stages.” (She later clarified that she’s just taking a break “and will come back stronger than you’ve seen.”)

“It’s not the first time in history bigots feel emboldened, but now it is back in force,” Gondelman said. “There are communities that faced open prejudice without abatement for years, and then, foolishly, we thought, ‘Oh, for Jews we’re working towards an intersectional embracing of other cultures.’ But maybe for Jews that time is over, and people can say their worst thoughts in their worst voice.”

Though his comedy can be edgy, his nice-guy persona holds because that’s essentially who Gondelman is at heart. One could even use the M word when describing him: mensch.

“I’m not that mysterious or dark,” he said about his demeanor on stage and off. “Occasionally people will say to me, ‘You must secretly be a serial killer.’ People don’t expect me to be a sweetheart. But [in comedy] you don’t have to be clean to be nice, and you don’t have to be nice to be clean.”

Dan Pine

Dan Pine is a contributing editor at J. He was a longtime staff writer at J. and retired as news editor in 2020.