TSJ Interviews Comedian Zach Sherwin

YOU MIGHT NOT BELIEVE the combination of comedy and hip-hop to be ideal, but it looks as if that angle is quite flawed. It seems the community is littered with the past and present punchlines of great poets and artists. Rapper/Comedian Zach Sherwin is a prime example, having made a career of fusing hip-hop and stand up comedy together alongside some of the best in the comedy industry. His background is different than many in the community – which is noted in his song “Street Cred.” Regardless, Sherwin found an artistic outlet in hip-hop and an opportunity in comedy. Today, he has created a prime position for himself that proves to have been not only well taken but also truly original, earning himself the title of an MC and a poet… like many in the hip-hop world.

Sherwin recently spoke with TSJ about the poetry of hip-hop music, the importance of lyrics, it’s fusion with comedy, and his part in the hysterically popular “Epic Rap Battles of History” web videos.

The Smoking Jacket: You’ve got a very interesting background. Would you consider yourself a comedian or rapper first?

Zach Sherwin: Well, I came to this through hip-hop. I started rapping when I was around ten years old but didn’t introduce it until I started doing sketch comedy years later, which had nothing to do with hip-hop.

The way it shows for me most clearly is that comedians are always able to recite bits from their favorite comedy albums, word for word. For me, I don’t really have that. It’s much more like that for me with hip-hop albums. So I think of myself as a rapper but I tend to do comedy rooms, comedy venues and festivals. I package myself as a comedian but my enthusiasms gravitate towards hip-hop. If I had to drop one, either comedy or rapper, I’d drop comedy.

TSJ: Are there a lot of comedic rappers around? I don’t know of many.

ZS: I think it kind of depends on how you define it. There are very obvious yeses. Howard Kremer does a character Dragon Boy Suede. He’s a stand up in LA and a writer, but also releases hip-hop albums through his alter ego. His stuff is fantastic.

There’s also a guy named Eric Schwartz aka Smooth E. He has raps about Chanukah and Passover but he released a song called “Clinton Got a Blowjob” that went viral a couple of years ago. And of course, there’s guys like The Lonely Island, who are probably the most famous. I admire what they do.

My favorite rapper is a guy named MF DOOM. He’s 100 percent a comedy rapper but doesn’t sell himself that way. He packs his material with punchlines and wordplay. It’s so great. But also Lil’ Wayne, I think he packs his songs with jokes. I love that guy. I think he’s doing comedy all over.

TSJ: Hip-hop sort of fascinates me. A lot of it can be about respect. Your video for “Street Cred,” is that true in the sense of your background and upbringing?

ZS: Oh my God, it’s all true.

TSJ: So when did you realize that not only did you like hip-hop, but that you were also good at it?

ZS: I started listening to rap when I was ten and started writing my own stuff almost right away. It really is the cliché of finding your voice. At first, I started out writing like the material I was listening to: Wu Tang Clan, Cypress Hill and Naughty By Nature. I knew it was a joke for me to be writing that stuff at the age of twelve but I did it for a long time. Then when I was 17, 18, I couldn’t stomach writing material about bitches and drugs anymore.

When I was 23, I wrote this rap about when I got pulled over by a cop on my bike for running a red light. Audiences seemed to really connect with that. I had performed some raps for audiences with my sketch group but it never felt the way it did with that one song. So it took me a little over a decade of writing to discover I wanted to do it all the time.


TSJ: I think that makes sense. In any art form you emulate the people you like until you find your own voice.

ZS: Yes, I think that’s right. I hear stand ups say that all of the time. And it’s definitely true for me too.

TSJ: So would you go to comedy venues and clubs in the beginning to perform?

ZS: Myq [Kaplan] plays a big part in this story. I was performing with my sketch group was sort of gravitating towards comedy venues. Then Myq and I did a show together at Brandeis University, where we both went to college. At that show it was my sketch group as the headliner and Myq going second. Myq should have gone first because my group ate shit on that show. [laughs] Everyone else did great, and I noticed that they were doing their own thing.

I remember talking to Myq before the show and saying I wasn’t excited about what my group was doing anymore. There were some good things to it, and I know that in a group situation you have to make creative compromises, but I felt I was really compromising a lot. I had done my bike stop song, because at my insistence, my sketch group would incorporate one rap song per show.

After that show, Myq told me he had an open mic and I should go and just perform that song. So I did it and it went great. Afterwards, he invited me to perform at a show he hosted at The Comedy Studio. It was an instant click at that place. I was able to then get stage time and eventually get an agent and did the Montreal Festival. It all just happened in the comedy world. I’m really grateful for that because I appreciate the honesty and authenticity and lack of affectation that are emphasized so strongly in comedy.

“I package myself as a comedian but my enthusiasms gravitate towards hip-hop.”

TSJ: I get that. Did you find that the crowds were onboard rather quickly?

ZS: Yeah, I would say so. I’m sure if I were to watch some of my earlier performances I would cringe and not be able to make it through, but I think I got really positive feedback early on in Boston. I’m not saying I was a superstar. I felt very much like an outsider during my sketch group days but when I started doing performing with just me I felt a part of the comedy community.

TSJ: And you had something different, which is great.

ZS: It definitely did help me stand out, yes.

TSJ: Given your upbringing, which you have mentioned on “Street Cred,” why do you think hip-hop resonated with you so much?

ZS: I’ve always been into words and poetry, which is true for a lot of my family. My mom was an English major and there was always a lot of literature around growing up. It’s kind of in my DNA. But I grew up not having a dad around. I haven’t been in touch with him since I was two or something, and I do think hip-hop, in little ways, acted as a father figure. I was looking up to guys that were older and I was really hungry for those male role models when I was a kid, so I think hip-hop played into that.

But aside from that, I have always just loved words. I started reading really young and hip-hop is so verbal. All the mastery of the craft is concentrating on the words. It’s very challenging and rewarding.

TSJ: Speaking of that, did you happen to see “The Art of Rap”? It’s Ice-T’s documentary about hip-hop.

ZS: It came and went but I really wanted to see it.

TSJ: It’s on Netflix Instant. I watched it and realized that I never put that much thought into how artistic hip-hop music is. The words, the beats, the freestyling and just the basic rhyming, it’s a fascinating art form that I never thought about like that before for some reason.

ZS: Yeah, figuring out all of that stuff is incredibly exciting. Talking about hip-hop blows my skirt up in a way that comedy doesn’t. When Eminem started changing the way that syllables should be emphasized and stuff; that is so fun and thrilling. Now I think the thing is the opposite, where people take words that are identical and approach them at different angles.


TSJ: You’ve also done something I think is very cool, you’ve written and performed on the “Epic Rap Battles of History.” How did that all happen?

ZS: Yeah! There’s two guys who are the principal dudes behind “Epic Rap Battles.” One is Lloyd Ahlquist and the other is Pete Shukoff aka EpicLLOYD and Nice Peter. Lloyd and I met right after I graduated in college in 2002, maybe 2001. He had a comedy show that my sketch group performed at. Lloyd and I used to get drunk at parties and just freestyle, we were really into it. We stayed in touch, it was one of those friendships where you don’t see each other much but when you do you’re right back on.

When I moved to LA in 2010, I knew he was here running a theater. He and I started working on this all-freestyle comedy show, and we put it up a few times, but one of the things we tried to do was to have audience members suggest historical figures for us to freestyle battle as. It was a super primitive “ERB.” Pete was helping us out with the show and was just starting his YouTube channel up at the time. He got very excited at the idea.

The show kind of folded but Lloyd and Pete really took that seed and grew it out. And when the battles started taking off they realized they were going to have to produce a whole lot of material so they hired me on the writing staff. And around the same time they cast me in my first one. I’ve been in three so far and I write on all of them.

TSJ: That must be a very fun position to hold.

ZS: Dude, I’ve never been a part of something like this. It’s crazy. I perform a lot on the college circuit and right now colleges are the sweet spot for “ERB.”

TSJ: Oh, I bet! They probably love that.

ZS: It is wild! They introduce me from the “Epic Rap Battles” now and such. It’s great! I did one of these conferences at a college recently, and someone came up after and said their brother was in Afghanistan and his favorite video was the battle that I was in, the Albert Einstein / Stephen Hawking one. They asked me to take a picture with them and sign something because it would mean so much to the brother. I was like Jesus Christ!

TSJ: That’s wild man. Very cool stuff.

ZS: It was very humbling. That’s why I’m slaving over these funny ideas in coffee shops. I mean, that’s so cool! I’ve never been a part of something this viral and big. I’m very lucky.

TSJ: Did you happen to work on the one with Snoop Dogg at all? Or Snoop Lion?

ZS: Yes, I did!

TSJ: How was that?

ZS: It was great! I had a bunch of lyrics in there, which is amazing. You never know how much of your stuff will end up in there. You send some stuff and never know. But that one, I had a lot of good lines in and got to watch Snoop say them!

The actual day of the shoot he wasn’t available for hanging out but I was outside while they were shooting it. We caught each other in the hallway and sort of gave each other a nod. [laughs] But watching that video, it is very cool! His early stuff is something I definitely used to listen to so to hear him say lines that I wrote is pretty unbelievable.

TSJ: I was going to ask if the “Epic Rap Battles” have at all helped you gain a crowd but it sounds like it has.

ZS: The nicest thing for me is when I have my own YouTube videos go up “Epic Rap Battles” will tweet it out and promote me on YouTube and such. It’s a lot of support. A lot of the views I get and people that subscribe to me, it’s largely attributed to those guys at “ERB.”

TSJ: You had mentioned doing the college circuit. Do certain parts of the country react differently to your material and performance than others?

ZS: I don’t know really. I just signed up to do a Northern Plains region thing and am playing in North Dakota too. To be honest, I don’t know how it’s going to go but that’s very exciting to me.

TSJ: The cool thing about music, to me, is that at least you know that you can rap. There really isn’t a way they can leave and be like, well he just was not good.

ZS: Yeah, I totally get what you’re saying. At college shows, you have sixty minutes to perform and there are no eyes on you in terms of industry people. If a show is going well today, I’ll probably spend 75% of the time talking to the crowd and doing spoken word material, then I’ll do six or so songs.

So yeah, if I’m ever bombing, I can just go to a song. But doing a song over and over, sometimes you find more fun just being in the moment and riffing and doing crowd work. Having said that, I always want to start and end the show on solid songs.


TSJ: So how often are you writing new material?

ZS: All the time. I try to write everyday. My pace seems to be to put a new song onstage about every two weeks. Sometimes they aren’t close to finished but they are good enough to perform in front of people.

TSJ: In comedy, music, etc., some find themselves to be better writers, some better performers. Where do you think you are better?

ZS: It’s funny. Shane Mauss… have you interviewed him?

TSJ: I have, for TSJ actually. He’s a fascinating guy.

ZS: He is a fascinating guy! But Shane says that he doesn’t like performing. For him, it’s all in writing the joke. The performance is an afterthought. And Myq [Kaplan], I feel writes constantly but his mouth generates a stream of riffed material. I’d put myself right in between them.

For me, it’s about making time to sit down with a pen in hand at a place where I can concentrate. I like knowing that I have those hours logged to write. And I know that I wouldn’t have any support to finish that if I weren’t putting it in front of crowds. Having a deadline of a performance really helps me envision what will help a song and make it push through. It would be interesting to see how it would work if I gave a verse or chorus or lyric room to breath if I didn’t have the pressure of succeeding in front of audiences.

TSJ: Do you write the material thinking something will be funny or do you write more so to impress people with the music?

ZS: I want stuff that isn’t flashy. I want something that’s good, a concept that is not for showing off. So for comedy shows, I go for something that is worth the pay off. I know there might not be laughs all of the time but when they come it’ll be good. YouTube has been a really nice place for me to not be so tied to that. An example would be “Pro/Con.”

TSJ: That was going to be my example. I like that one.

ZS: Thanks! That one has no jokes in it. Maybe a few smile moments, but I don’t know if that counts as comedy. It’s more of a cool concept and execution.

And this new song, “Stage Name” – which reminds me, I’m no longer using the name MC Mr. Napkins. I’m about to make it official online. But “Stage Name,” I recently shot a video for that song. That one has literally zero comedy. It’s the most earnest song I’ve ever done, and that’s really nice. I want to be a guy who doesn’t need to be on all of the time.

TSJ: So are you veering off of comedy and heading more towards straight rap?

ZS: I think my next album will clear the backlog of stuff that I wrote in between my first album, which came out in 2010, and now. I think early on I was writing stuff that was a bit more silly and whimsical and just choosing topics because they were so unlikely. Sort of like, Who would have ever thought about this? Those were great; they opened a lot of doors for me. But now I probably wouldn’t write it.

I think my next album will be much more overtly comedic. There will always be comedy in my rap. I just want to say something. I’m excited about the direction my stuff is going in.

TSJ: Obviously you’ve shown yourself to the comedy world, and they’ve responded very well. Have you had any interaction with the rap community?

ZS: Nothing significant. I’ve had a couple of cool things here and there, music festivals and such. I did share a billing with Jay-Z, but he was at the very top and I was way at the bottom. [laughs]

TSJ: When you’re writing a song, what’s more important: The beat or the lyrics?

ZS: Lyrics, for sure. Usually, I’ll come up with something that catches my attention. If it’s interesting I’ll try to blow it up from different angles to where I have two or three minutes, and only then will it be time to try to do interesting things with the beat and cadence and stuff. I love music but I don’t make it myself. The language, meaning the lyrics, that’s what I control.

Zach’s website: mrnapkins.com

Zach on Twitter

Zach on Facebook

Related on The Smoking Jacket:
TSJ Interviews Comedian Erik Griffin 
Five Musicians Who Should Start Doing Drugs Again
TSJ Interviews Comedian Myq Kaplan