He raps up laughs

But the beat drops, and something much more interesting happens. Napkins has flow. He's actually good. And what in the world is he talking about? Blood pressure cuffs? Mussolini? Spelling bees?

For the 28-year-old Sherwin, a fan of rappers like MF Doom and MC Paul Barman, hip-hop is the perfect vehicle for his oddball comic vision. "It's all about punch lines and verbal wittiness and verbal facility and cleverness," he says. "It's amazing the level of punning that goes on even with hard-core gangsta MCs. So it was really something I could easily tap into in as goofy [a] way as I wanted to."

His inspiration comes from personal stories, like his defeat at the sixth-grade spelling bee because he couldn't spell "irrevocability," or from random things that catch his eye. He came up with his rap "Sphygmomanometer" (better known as a blood pressure cuff) during a long wait at the doctor's office. "I like anything that has good words associated with it and lots of colorful vocabulary," he says. "I really delight in this kind of thing."

Sherwin's quirkiness has made him one of the hardest working comics in Boston just two years into his solo stand-up career. He was scheduled to help kick off this week's AltCom Festival on the now-canceled Michael Showalter/Michael Ian Black show (he's still on the AltCom bill Saturday at the Burren), and he hosts Thursdays at the Comedy Studio and frequents ImprovBoston, which is just a few streets away from his Central Square apartment. Boston Phoenix readers just voted him "Best Local Comedian." He was also chosen to be part of the Just for Laughs festival in Montreal in July.

He's also one of the few local comics with industry representation, signed to the Gersh Agency on the strength of his YouTube videos, and soon he's going to be featured in a major Web campaign for a soft drink company.

But that same quirkiness also makes him hard to categorize.

Comedy Studio owner Rick Jenkins remembers hearing about "this high-energy guy who does funny raps" and thinking Napkins wouldn't be a fit for his club. But then he caught the act at an open mike and found Napkins's wit and skill "astounding." Eddie Brill, "Late Show With David Letterman" talent coordinator and audience warm-up comic, caught Napkins at the Studio in April and thought he was quite funny but saw the rap shtick as a safe comic route. "I wouldn't classify it as stand-up comedy, but I thought he was very smart and funny," he said. "He has great fun with words and that pulls on my comedy heartstrings."

Sherwin has been writing raps since he was a kid growing up in Ohio and Missouri, discovering bands like Cypress Hill, the Wu Tang Clan, and the Beastie Boys at Jewish summer camp. He found comedy when he came to Brandeis and started the Late Night Players comedy troupe. The Players toured colleges for eight years, which gave Sherwin a paycheck but not much creative inspiration.

The Napkins character energized Sherwin to write more, and, surprisingly, to be a bit more genuine onstage. He recently found some notebooks from his teenage years, full of embarrassing faux gangsta angst and boasts about how he could take on any MC, even though he'd never been in a rap battle - and still hasn't. In reality, he's a friendly guy who works as a Hebrew tutor a few hours a week.

Friend and fellow local comic Shane Mauss was the one who put Sherwin on Gersh's radar (he signed with them two years ago). He respects Sherwin's talent but thinks his personality has also helped him rise quickly.

"I think that he is extremely intelligent and original without being snobbish about it," he says.

Sherwin may still write the occasional battle rap - including one comparing himself to Captain Chesley "Sully" Sullenberger in which he calls out haters he calls "goose MCs" - but otherwise, Napkins is only a slightly exaggerated version of himself. If his raps are sometimes nerdy, it's because he's interested in nerdy things.

"I don't know if I would even call it a character," Sherwin says. "I just think of it as me, rapping."