Theater & art

Zach Sherwin back in town with a rap and a joke

Zach Sherwin
Zach Sherwin

American show business is rife with hyphenates: singer-songwriter, actor-director. Brandeis University graduate Zach Sherwin has found his own: rapper-comedian.

There have certainly been rappers who have relied on humor — think Eminem, Biz Markie, the Beastie Boys — but Sherwin aims for songs that, while sometimes emotionally affecting, are funny through and through. And though he is a capable rapper with two albums on comedy record labels (“MC Mr. Napkins: The Album” in 2010 and this year’s “Rap!”), he is most surely a comedian.

Sherwin, 35, said that as much as he’s an enthusiastic member of the comedy scene, his first love is rapping. He’ll bring both talents to Johnny D’s in Somerville on Thursday. He counts Mos Def, Method Man, and Q-Tip among his influences.


“I’ve been writing raps since I was 10,” Sherwin says over the phone from Los Angeles, where he is based. “I always enjoyed performing in various capacities in college and junior high. I was always a showoff, attention-y kind of kid. Comedy just kind of happened. I found it fun and interesting, but I didn’t really take it too seriously.”

Get Today's Headlines in your inbox:
The day's top stories delivered every morning.
Thank you for signing up! Sign up for more newsletters here

It happened at Brandeis, where Sherwin connected with some like-minded showoffs and formed the Late Night Players, a sketch comedy group that performed regularly on campus and played the college circuit for several years afterward. Along the way, Sherwin rapped his way around the Boston comedy scene. The group disbanded amicably in 2009, and Sherwin headed to Los Angeles the following year. Since then, he has not only released albums but also made television appearances on “The Pete Holmes Show” and “Totally Biased with W. Kamau Bell.” He’s also starred in the enormously popular Web series “Epic Rap Battles of History” (on which he rapped as Stephen King, Sherlock Holmes, and Doc Brown from “Back to the Future,” among other characters).

Sherwin’s raps — which range in subject from funny words to father figures — have a deft playfulness to them, as if he knows how strange it is to rap about, say, sphygmomanometers (blood pressure meters) or a viral video about a baby biting a toddler. But his raps have become more personal in recent years, which is one of the reasons he decided to shed his longtime rap moniker MC Mr. Napkins.

“There was nothing about having the name anymore that felt meaningful to me,” Sherwin says. “I felt like sometimes it was holding me back. It was like a mask, a thing to hide behind. Now that it’s eight years down the line, I don’t feel like I need it anymore.”

He says the shift allowed him to focus on topics that were not “overtly comedic,” such as in the new track “Pop Music,” in which he raps about how his parents’ divorce prompted him to look for male role models in Naughty by Nature, the Notorious B.I.G., and Wu-Tang Clan.


Another recent development is Sherwin’s focus on traditional stand-up comedy, which he has been incorporating into his act more and more. He said he was partly inspired by touring with Bell, who took an interest in Sherwin after seeing him on “Epic Battles of Rap History.”

Bell, in an e-mail, says the decision to tour with Sherwin was easy. “After working with him on ‘Totally Biased’ twice, I knew my stand-up audience would love him, and they did. Even though on the surface it may seem like we are an odd pair, we’re not. We’re both using comedy as a way to explain the world to ourselves. And we both have hope for the future in this horrible present. Also he taught me a lot about hip-hop. And I taught him a lot about — I can’t think of it now. But I must have taught him something.”

Sherwin says he learned a lot from Bell. “He was really enthusiastic and supportive. I have been, and was, trying to consider what I wanted to talk about onstage. It was really cool to watch Kamau talk with such skill and with such great jokes about what was happening in the news right then.”

Among Sherwin’s most recent projects is a podcast called “Words of the Years,” in which Sherwin and fellow comedian Myq Kaplan discuss the Oxford Dictionary’s “word of the year.” The podcast just wrapped its limited run, but all episodes are available online.

As for what’s next, Sherwin is looking forward to keeping his act fresh for himself and his audience, and traditional stand-up is part of that evolution. “If I have a new thought that I just want to talk about that doesn’t merit getting built out into a rap, it’s really nice to give myself permission to talk about it in stand-up and not feel the pressure [to turn it into a song]. For bigger shows that feel like a heftier thing, if I’m headlining, it’s fun to do some songs.”



At Johnny D’s, Somerville, Thursday.

Tickets: $12. 617-776-2004,

David Brusie can be reached at