It is impossible to write about Josh Gondelman without addressing the “nice guy” thing. His gentleness radiates through his stand-up comedy and his writing. He offers pep talks to Twitter followers. “I’m like if a cardigan were a person,” he says in his opening bit from 2019’s “Dancing on a Weeknight” album. “I think we’re going to have a really nice time,” he adds, “but I would say that.”
Desus Nice, Gondelman’s boss on Showtime’s “Desus & Mero,” confirms that status. “Josh keeps a very neat office,” he says. “He gives good hugs, and he’s probably one of the most supportive human beings you’ll ever meet.”
Increasingly, the Stoneham native is trying to redefine — or at least deepen — that image. In his new book, “Nice Try: Stories of Best Intentions and Mixed Results,” he writes about the difference between a good person and a nice guy. Though he is, as a rule, against violence, he writes, “I come down squarely on the side of people who punch Nazis, simply because it rules when bad things happen to white supremacists.”
Being a good person means engaging with the uglier aspects of daily life and trying to help, even if that means throwing an occasional punch. “Because sometimes the best way to be kind is to not be nice,” he writes.
Speaking by phone from his home in New York City, Gondelman says that “kind versus nice” philosophy is more a life goal than a professional one, but he does try to work it into his stand-up, too. “I’m trying to be a rounded, nuanced person onstage,” he says. “I’m not just like, ‘Hey, isn’t everything terrific?’ But I do think there’s so much that is useful about being kind and nice onstage that people aren’t necessarily used to seeing.”
There can even be something edgy about that niceness, as opposed to a seething comic hoping to capture the rage of a Sam Kinison or Bill Hicks. Gondelman has given himself room to be subversive. “You think of edgy, right, as being, ‘All right, I’m going to say what we’re all thinking,’ ” he says. “But that’s not interesting. If everybody thought it, that’s not an insight.”
Much of the new book and album are made up of personal stories — how a Michael Jackson impersonator came to perform at his wedding or how his neighbor caught him singing rap songs to his pug, Bizzy. But he’s also included some political and social commentary. As a former preschool teacher, he talks about how no teacher he knows would support the guns-in-the-classroom policy advocated by President Trump, and he delves into what he saw as the hilarious stupidity of people protesting Nike for its association with quarterback Colin Kaepernick.
Gondelman notes that the political bits don’t go over as well as some of his other material, but it was important for him to include them on “Dancing on a Weeknight” to give the listening audience a more complete picture of who he is. “They’re things I think and believe in," he says.
When Desus and Mero moved their late-night talk show from Vice to Showtime, they weren’t used to having to run a writers’ room. Gondelman came over from the team on “Last Week Tonight With John Oliver” that had won four Emmys and two Peabody Awards to become their writer-producer and help get the new staff in place.
Desus says that “nice” is an apt description, but Gondelman is no pushover. “To be nice in New York, that usually has a connotation that you’re a sucker or a target or kind of Pollyanna-ish,” he says. “And Josh is none of that. Josh is somehow nice but he has that big city edge where you’re not gonna take advantage of him.”
“Humble” is also a fitting word to describe Gondelman. Sure, he’s had some embarrassing moments, like trying to ingest ecstasy to impress a date or living with his decision to shave his hairline for a high school production of “Much Ado About Nothing” to look more like Michael Keaton. But he has also helped build two high-profile shows in “Last Week” and “Desus & Mero” from the ground up, is a successful touring and recording comedian and author, and has a new podcast coming out this spring. And that’s before you count a happy marriage. That casts some doubt on the “Mixed Results” of the book title.
“Professionally I’ve had great results, and personally it’s increasingly positive,” he says. “My wife is amazing, we have such a lovely life together. So the results, I think, are increasingly positive over time. Which is the right way to trend, I hope.
"Maybe my next book will be super arrogant. I’ve got the humility book out of my system, and the next one is just like, ‘Kiss My [Expletive], The World!’ ”
Gondelman’s previously scheduled shows at Laugh Boston March 13-14 have been postponed. New dates have not been announced.