Anyone who has known Josh Gondelman for more than five minutes will tell you — he's a really nice guy. He knows this is how people see him, and he'll take it. It's a good feeling to have people think about you at all, and he knows they are being sincere. The only problem is, when someone in comedy calls you "a nice guy," it's usually not the best of compliments.
"That was kind of a reputation before I had any external markers that I'm at least a serviceable comedian and writer," Gondelman says in a telephone interview, speaking from his Brooklyn, N.Y., apartment. "It's a very funny place to start, because unless people have a reason to think that you're funny, it sounds to people in comedy that you're not very funny."
Rest assured, Gondelman, who records a new CD Thursday at the Davis Square Theatre, in Somerville, is very funny. And there is a lot of proof now to back that up. Since moving to New York in 2011, the Stoneham native has landed a job on the Web team at "Last Week Tonight With John Oliver" and was promoted to staff writer at the end of his first year. In September, publisher Plume released "You Blew It! An Awkward Look at the Many Ways in Which You've Already Ruined Your Life," a humorous self-help book he co-wrote with Joe Berkowitz. And his reputation as a stand-up has continued to grow.
Gonelman's delivery is mild-mannered, and he did name his 2011 CD "Everything's the Best!" While he may have routines about how adorable his preschool students were when he was teaching, he also talks about shocking a pharmacist when ordering a Plan-B pill after a one-night stand. He may call the new CD "Pathological Sweetheart," a description given to him by a writer in New York. "My comedy isn't clean, it's just friendly," he says. "So I get asked to do a lot of clean shows. It's like, oh, I have a clean vibe, but I say gross, weird stuff. It's just it's very gentle the way I say it. It's not upsetting or jarring to people, because I'm not very aggressive."
Boston comedy has a reputation for producing rougher-edged comics, like Denis Leary and Lenny Clarke. But there are plenty of comedians from here who don't fit that mold, like Paula Poundstone and Steven Wright, who are keen writers with a more subdued stage presence. Gondelman fits that description. "There's a second vein of people that came from Boston like Brian [Kiley], who's super sharp, or like Myq Kaplan, who's super sharp but he doesn't have that kind of aggressiveness," says Gondelman.
When Gondelman was hosting an open mike at Sally O'Brien's in Somerville, it wasn't unusual to see him offer a comedian suggestions for tagging a joke or alternate punch lines. He loves the mechanics of comedy and loves to talk shop with fellow comics. "I have kind of like a joke brain," he says. "I like that kind of joke math and problem-solving. And it's fun."
He's had to do some of that type of problem-solving as a staff writer on "Last Week Tonight." Gondelman, who's never been a political comic, finds these days he has to spend more time studying current events. "Sometimes there's more background reading I have to do just to be, like, now I get it," he says. "And I like that. I'm happy to be informed. But if I'm off for two weeks in a row, I come back and I have to catch myself up a little bit because I probably will have read a little less hard news."
The writing gig allows Gondelman time to do six or seven sets around New York every week. It also rescued him from having to audition for commercials, where he would invariably wind up in a room with 15 people who looked just like him. "I would go up for basically anything and I ended up auditioning for a lot of things like 'idiot husband,' " he says. "I mean, that wasn't what it was called but I'd be the guy that was, like, 'OK, you're in the rain and you're calling your wife because you don't know whether you have car insurance.' "
Even better, he's writing on a show he actually likes, which isn't always a given for a comedian. "When the show comes out on Sunday, I get to be, like, Oh, I like this!" Gondelman says. "This is a fun thing to watch."
STRANGE BEHAVIOR PRESENT: JOSH GONDELMAN LIVE ALBUM RECORDING
At Davis Square Theatre, Somerville, Dec. 17, 9 p.m. Tickets $11.54.
Nick A. Zaino III can be reached at firstname.lastname@example.org.