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NEW YORK — It’s hard to tell if Jon Rineman is having fun.

At 32, he’s the head monologue writer for “The Tonight Show With Jimmy Fallon,” the apex for someone whose ambition is to make people laugh. Yet sitting in his closet-size office at Rockefeller Center, Rineman looks uncomfortable, as if he doesn’t belong.

“Everyone here is so fun and cool, and I’m just kind of this weird, lame guy,” he says. “Sometimes, I wonder how I’ve lasted.”

His colleagues and fellow comics know. They say Rineman, a 2005 Emerson graduate who’s worked for Fallon for six years, is indeed dorky, but he’s also a skilled and prolific joke writer. As relentlessly earnest as he may seem, Rineman can grind out dozens of gags a day, and a good percentage of them make it into Fallon’s monologue.


“He’s like a technician. He knows how jokes work, how to craft them,” says comedian Anthony Jeselnik, who had a hand in hiring Rineman at “Late Night With Jimmy Fallon.” “I don’t want to use the word joyless, but Jon’s approach is very workmanlike.”

Still, it’s fatiguing being funny every day, and Rineman isn’t sure how long he can keep writing one-liners. Perhaps with an eye toward life after “The Tonight Show,” he’s been honing his stand-up routine, making three or four club appearances a week after wrapping up work at 30 Rock. He is performing three shows at Laugh Boston July 9-11.

On a recent weeknight, after watching the 5 p.m. taping of “The Tonight Show” and meeting with the other writers, Rineman sat alone in his office for two hours working on jokes. He then grabbed his backpack and headed to The Stand, a tiny comedy club on Third Avenue, where he ran through five minutes of material. He quickly got back on the subway, and arrived at the Greenwich Village Comedy Club in time for a 15-minute headlining set at 11 p.m.


“Stand-up is the sport I get to play after school,” he says. “There’s a big difference between what’s funny on TV and what’s funny in a club.”

School is where he first discovered his penchant for punch lines. The son of an airline pilot and a journalist, Rineman grew up in North Hampton, N.H. He was a decent student, but found it easier to remember historical events if he added a joke. (“You know, like, ‘Then they all went to Applebee’s.’ ”) He was also a talented athlete, but a diagnosis of rheumatoid arthritis, a painful condition that caused his joints to swell, steered him toward comedy.

“I felt very self-conscious, very nervous, because I was worried about my appearance,” says Rineman. “That’s when I realized I could use comedy as an icebreaker.”

But comedy is a competitive business, as he learned at Emerson. It turned out he wasn’t the only kid who did Jay Leno impressions, could recite whole scenes of “Seinfeld,” and stayed up late deconstructing the monologues of David Letterman and Conan O’Brien.

“You walk into Emerson and there are 13 other guys just like you,” he says. “That was a rude awakening.”

While in college, Rineman mustered the courage to try stand-up at The Comedy Studio in Harvard Square. It didn’t go well.

“I bombed a thousand bombs,” he says. “It was the absolute worst. I was supposed to do a 5-minute set, and I think I got through 3½ minutes. When you’re not getting laughs, you get through the jokes a lot quicker.”


Instead of giving up, Rineman tried again the next week and fared better. Mike Bent, who teaches comedy writing at Emerson, says his former student is funny, but also has a ferocious work ethic. It’s not unusual for Rineman, who lives in Queens with his wife, to stay up until 2 a.m. writing jokes for the next night’s “Tonight Show.”

“Jon’s one of those guys who really wanted to do this, so he worked constantly,” says Bent. “He realized it wasn’t enough to be funny. He needed to make it happen.”

Rineman’s break came after graduation when a family friend who grew up with Jay Leno in Andover agreed to pass along his material. That was on a Saturday. The following Monday night, Leno called Rineman at his parents’ house and invited him to join a group of freelancers who faxed jokes to “The Tonight Show,” with no promise that their stuff would be used. But Rineman’s frequently was, and the arrangement, which paid a paltry $75 for each joke used in Leno’s monologue, lasted for four years.

Rineman also faxed bits to “Saturday Night Live” for the “Weekend Update” segment, hosted then by Seth Meyers, and to “Late Night With Jimmy Fallon.” Eventually the “Late Night” writers, impressed with the number of jokes Rineman generated on a daily basis, summoned him to New York to interview for a job. He was 26 and living at home with his parents.


“In baseball, Jon would be a singles hitter,” says Jeselnik. “He never hits a home run, but he’s good for a couple of singles a game and has a good average.”

Rineman is not the stereotypical comedian, zany and backslapping. He has the bearing of a statistician: soft-spoken, pale, cheerless. For the “Late Night” interview, colleagues recall, he dressed in khakis, tie, and a blazer — like a nerd, in other words. His hipster quotient is low. Rineman’s idea of a great TV show is “Everybody Loves Raymond”; his favorite bands are the Barenaked Ladies and the Beach Boys. (He met his wife, Rebecca Wasserman, at a Beach Boys concert in 2009.)

“Jon’s such an unapologetic dork,” says Jeselnik. “When he first arrived, no one made fun of him because they thought he might show up with a gun. But he knows who he is, and he’s got a great sense of humor about himself.”

Rineman couldn’t quite believe he got the job. “I think their big reason was, like, if we don’t hire this guy, who will?” he says, only half joking.

It was daunting to join a staff that included established comics like Federman, Jeselnik, Morgan Murphy, and Jeremy Bronson.“I didn’t want to get on the elevator,” he says. “I was, like, this isn’t going to work. They’re going to find me out. But I got off to a fast start and everyone was so nice to me.


“My life was saved by those people,” he adds quietly.

It’s after midnight and Rineman is standing on the platform at the West 4th Street subway station, looking at his phone. He was pleased with the crowd’s response in the clubs. But he isn’t smiling.

“I can’t laugh at my own jokes,” he says. “I like when the audience laughs. But when the other writers laugh, or Jimmy laughs, that’s a really good feeling, because they know how hard this is.”

”Stand-up is the sport I get to play after school. There’s a big difference between what’s funny on TV and what’s funny in a club.” said Jon Rineman on writing jokes for “The Tonight Show” and performing them in a stand-up set.
”Stand-up is the sport I get to play after school. There’s a big difference between what’s funny on TV and what’s funny in a club.” said Jon Rineman on writing jokes for “The Tonight Show” and performing them in a stand-up set.Peter Foley for the Boston Globe/Globe Freelance

Mark Shanahan can be reached at shanahan@globe.com. Follow him on Twitter @MarkAShanahan.