Where Comedy and Rap Meet with Zach Sherwin

Tall, thin, white, and Jewish, not exactly how you’d describe most rappers. But that’s exactly how you’d describe Zach Sherwin; only you’d also include the adjectives funny, and as nice as can be. The LA-based comedy rapper has been seen on Totally Biased with W. Kamau Bell, The Pete Holmes Show, and is part of the hilarious YouTube series Epic Rap Battles of History. Now he’s got a brand new album out simply titled Rap!

How would you describe your style?

I try not to be too self-conscious about it, but I think comedy rap can bring images of, you know, white dudes pretending to be thugs and sort of clowning themselves a little bit. That’s not what I’m trying to do with the album. Just trying to have thoughtful songs that are also funny and really try to work on the musical end with the producers that I work with.

Where’d you learn to rap? I know you don’t go to school for it, but how did you develop that skill?

No, I didn’t, but there are rap schools you can go to. I think the rapper KRS-One had something. I have friends that give rap lessons.

I started listening to rap when I was about ten. You’re so malleable and open to influences at that age that I got really, really into it, before you know that you can’t and maybe shouldn’t do it. I started writing raps almost right away. Then I think it was just doing it over the intervening years. Sometimes I would write more actively and sometimes not at all, but I was always listening to it and thinking about it. When I really started doing it again I stuck to it rigorously, so hopefully the skills improve. I believe they say, “Practice makes perfect.” Now I’m perfect, because I’ve practiced.

Do you feel like you get push back from the rap or the comedy community?  If so, which is worse?

You know, it’s hard to say. There’s so much good out there that combine comedy and hip-hop that I think it’s probably from an older time that guys were like, “Yo, Yo, Yo! I’m MC Suburban.” I don’t think that really happens anymore. Even so-called mainstream rappers, there’s so much comedy and puns and wordplay… I mean Lil Wayne is funnier more often then he isn’t, for one example. I guess there are enough counterexamples that it’s no longer a stereotype I have to worry about.

I think as a comic, yeah there’s a bit of a bit of a stigma with it. I haven’t encountered a lot of active pushback, but I don’t know what anyone’s thinking. Hopefully they’re judging it on its own merit and not jumping to a conclusion on it. And then, from the hip-hop community, I don’t know. I move much more in the comedy circles than I do the so-called “legit,” hip-hop or you know, battle rap circles. But I have friends who are rappers and I haven’t encountered any active pushback on my stuff.

Have you ever done an actual rap battle that had nothing to do with comedy, like 8 Mile style?

No, I haven’t. That’s both just because the people that I know and the opportunities that get offered to me. But also, I do comedy related rap battling and its kind of fun, but I’m so much more a lover than a fighter. I don’t know that I would jump at the opportunity to do a serious rap battle where people were actually trying to tear me down. Once I did a show in Alabama and afterward this guy was like, “Hey man, wanna freestyle?” I was like, “Yeah, sure. I’d love to. I’d just want to freestyle. I don’t want to battle you.” He was like, “Cool yeah.” And then we started standing there freestyling with other people watching and he started coming at me really personally, like anti-Semitic jokes and stuff. I was kind of like, “What are you doing? We’re breaking the rules here.” So, yeah. Not really my scene.

Well, you’re there to make people laugh.

Yeah. People have really good bullshit detector, so I think if I was trying to be super aggressive battle guy it would ring false.

You’ve got a track on the album about how Big Pun rhymes the word “everywhere” with “I Own’t Care.” One of my husband’s biggest pet peeves is when Kid Rock rhymes “trying different things” with “smoking funny things” in All Summer Long. He just rhymes the word “thing” with the same word and it drives my husband so crazy he can’t even listen to the song. What are your pet peeves with rap? I know that’s kind of a weird question.

(laughing) I think about this stuff all the time. It’s not at all a weird question for me. So sometimes rappers will dazzle you with what they figured out to rhyme. I always go to Eminem. He’s the king of this, making unexpected rhymes with weird emphasis. He has a rhyme on his most recent major studio album where her rhymes “hysterical” with “bare knuckles” and he does it by saying “hyster-RUCK-le.” I just think that’s great! I didn’t even get what he was saying until I looked it up on some lyric website and I was like, “Oh! That makes total sense.” So that’s one end of it, going to great lengths to make crazy rhymes work and contorting yourself. It’s so great when you can pull it off.

Then there’s Nicki Minaj, who I think is one of the foremost practitioners of just rhyming a word with itself unapologetically. I mean, there’s no difference between line one and line two. She has a song that I have quoted on stage many ‘a time, where she says, “I guess I went commercial. Just shot a commercial. When I flew to the set though, I ain’t fly commercial.” So that’s the opposite of what Eminem is doing. And I think that’s okay too as long as you really lean into it and make it clear to everyone that you know that you’re doing it. It’s like an anti-choice. So that Kid Rock one you quoted I think is neither one. He’s not being ambitious, but he also isn’t also making it unmistakable to you that he realizes this rhyme is not a rhyme, so I back your husband up.

I’m sure he’ll feel greatly justified in his opinion.

I love the track where you rap about doing medical testing as a way to pay the bills. That’s part of being an artist, sometimes just doing what you need to in order to pay the bills. What’s some of the craziest or dumbest things you’ve done just trying to survive?

I had a job in Boston where I would just sit with people and they didn’t speak English well and my whole job was just to bullshit around with them. Just chat, make small talk for 15 minutes at a time. They would just pay however much for these 15 minute conversations. It ranged from people where I’d have to be like, “I. Said. How. Are. You?” to this German guy who spoke 98% perfect English and just needed super high-level conversation. He was a Buddhist and had been celibate for years and was super physically attractive and extremely successful in the corporate world. We would just talk. I would ask him questions, because his life was so weird and fascinating. It was so much more interesting than mine at the time. So, that was a pretty notable thing for me.

Were they paying you because one can’t really learn a language unless you use it conversationally, or were they lonely and wanted someone to talk to?

They were probably pretty lonely and homesick. They were in this strange country where they didn’t speak the language. I think it was like, “Get access to a native. Talk to a real American who has to listen to you and frustratedly move on from the conversation, because it’s so halting and infuriating.”

I picture it being like speed dating, “Ding!” and then you switch to the next person and have a conversation with them.

It was. I imagine that is as equally excruciating. I’ve never speed dated, but some of the conversations were pretty painful.

On one of your tracks you talk about how you’re trying to strike a self-deprecation tone with this album. Is that how you are typically in real-life?

It is. Just in general, I try not to take anything seriously. Like Nicki Minaj with that lyric, you know, there’s sort of a wink. Maybe self-deprecating isn’t exactly the right thing, but I just want to be like, “I get it you guys. It’s a comedy album. Have fun.”

Zach Sherwin’s album Rap! is out on AST Records now.

Where Comedy and Rap Meet with Zach Sherwin