Going Hollywood: Meet Zach Sherwin

Photo of Zach Sherwin by Mindy Tucker

People were going Hollywood long before Bing Crosby starred in the 1933 film musical Going Hollywood. Certainly, though, countless unknowns have packed their bags and moved to Los Angeles in the years and decades since then, hoping for show business to discover them and make them a star! New York City may be the city everyone goes to make it there before making it everywhere, but Hollywood remains the place where stars are born and made. It’s Show Business, USA. This is a recurring feature, a complementary West Coast version of Meet Me In New York, The Comic’s Comic’s mini-profile of newcomers, up-and-comers and overcomers of the Southland surrounding Los Angeles. It’s called Going Hollywood.

Zach Sherwin has such a way with words, he doesn’t need a fancy nickname to deliver them.

He had one, though, when I first saw him onstage at The Comedy Studio in Cambridge, Mass., across the street from Harvard University. His website says Zach Sherwin: rap + comedy. And just when I thought I couldn’t stand to see another white guy in comedy rapping, Sherwin proved the premise worthy of a second look, and many more listens. If I were to call him “the Eminem of comedy,” I would not be sarcastic or facetious in the least, for he is just such a linguistically lyrical beast.

I’ve been sharing Zach Sherwin’s music videos with you the past few years here on The Comic’s Comic, and even before that when he rapped under that MC moniker. Including his performances on Totally Biased with W. Kamau Bell and The Pete Holmes Show, he’s also earned a gold record from the RIAA for writing the “Albert Einstein vs. Stephen Hawking” single for YouTube’s multi-million subscriber hit channel, “Epic Rap Battles of History.” in which he has also portrayed such characters as Stephen King, Sherlock Holmes, and Egon Spengler. His latest comedy album, Rap!, came out this summer.

And this week, the brand-new Howl podcast app/platform debuted with a series, “Words of the Years,” co-hosted by Sherwin and current America’s Got Talent contestant Myq Kaplan in which the duo explores the most notable new words of each year from 2000 through 2014.

So let’s get to finding out how Zach Sherwin got from there to here and became such a delight in our ears!

Name: Zach Sherwin
Arrival date: Jan. 1, 2010
Arrived from: Cambridge, Mass.

When and where did you start performing comedy?

In my sophomore year at Brandeis University (go Judges! (the school’s actual mascot)), I started a sketch comedy group with some friends. We’d write and perform one show each semester, and when we graduated, we stayed in the Boston area and made a go of it. Real-world audiences were tougher than the crowds at our college, which were composed almost entirely of supportive friends, but we started performing on the NACA college entertainment circuit and pretty soon we were eking out a hand-to-mouth living. But there were six mouths between the six of us, which is a lot, and the hands feeding them weren’t that full because we never earned that much money. Eventually, other career paths started seeming more appealing than getting paid almost nothing for performing good-but-not-great sketches for inconsistently appreciative college students, and we started shedding members; when the group broke up, we were down to just three. But, having had some kind of creative breakthrough and I suppose, having sensed the group’s impending demise, I had already started writing short comedic raps. I was trying them out in our sketch shows, and, with the encouragement of Boston comedy allies like Myq Kaplan, Micah Sherman, Rick Jenkins, Erin Judge, Josh Gondelman, and Shane Mauss, I was also beginning to do spots around the open mike scene and at the Comedy Studio in Cambridge. So when the Sketch Comedy Local reached the end of the line, I walked right across the platform and hopped on the Rapping By Myself Express. (Disclaimer: I don’t really know how trains work since I live in L.A. and not New York.)

What was your best credit before moving here?

I did the Montreal Just For Laughs festival in 2009. I was very green but it wound up going just fine. I met people like Matt Knudsen with whom I’ve remained great friends, performed on and watched many terrific shows, and met the people who would become my managers. Ooh, this transition is gonna be perfect.

Why did you pick L.A. over NYC or anywhere else?

The people who would become my managers (see?) were adamant that I move to Los Angeles. And I was receptive to it. While I loved living in Boston, I felt ready for bigger and better and more numerous professional opportunities, and although I was traveling frequently to NYC to do spots, I just didn’t feel in my gut that moving there made the most sense for me. My managers insisted that they could create the most momentum if I moved to L.A., rather than go to New York or stay in Boston. I came out and visited for a couple weeks and did a showcase at the Hollywood Improv and got some stage time and discovered that I had more friends here than I thought and determined that it wasn’t the shallow, awful place that many of my fellow East Coasters had made it out to be.* I was eager to see just what my new managers were capable of, and I was eager for an adventure, so I took the plunge.**

*True story: a few days before I left Boston, I ran into a Boston comic who has since gone on to some prominence but who will remain nameless here. This person, who had had a few drinks, grabbed me by my shoulders and hissed in my face, “Go to L.A. Make your money. BUT NEVER FORGET WHERE YOU CAME FROM.”

**In my song “Switchitup,” I say “I used to cruise the Mass. Pike, then I headed more west, and now I holler ‘Pass the mike’ where the weather’s the warmest.” (But you have to pronounce it “wore-mest” for the rhyme to work.) To see it in context:

How long did it take to get your first paid gig in L.A. after moving here?

A long time, it feels like. I had paid work not in L.A. (soon after I moved, I booked a ton of shows in the Northeast region of NACA, so I was repeatedly flying across America to do college gigs I could have driven to in 45 minutes if I’d stayed in Cambridge), and unpaid work in L.A. (talking-head commentary on some cable countdown shows, which were my first TV credits but which earned me zero dollars, confusingly), but I probably wasn’t regularly combining in town + money until I started writing for the YouTube series “Epic Rap Battles of History” in mid-2011.

How is this scene better/same/worse than the scene you started in?

The thing I miss most about the Boston/Cambridge scene is the greater amount of overlap between the worlds of comedy and music. Music venues like Club Passim and the Lizard Lounge always welcomed comics, even non-musical ones. That community was very supportive, and it was a healthy change of pace to do stage time as a musician whose act included comedy, rather than a comedian who incorporated music. There are a few L.A. shows that have a comparable vibe, like Beth Lapides’s terrific Uncabaret and, to a lesser extent, WitzEnd in Venice, but the Boston thing is special.

Was there a moment when you felt your life and career really had “gone Hollywood,” and how do you explain it to friends or family back home?

I’m not exactly sure what “going Hollywood” means, but here are some answers and I hope one of them works. I used to and still do enjoy performing with comedians and actors and musicians I admire; I certainly get to do that here more often than when I lived in Boston. Getting my employee ID for the Warner Brothers lot when I worked for “The Pete Holmes Show” was exciting and felt like a milestone. Collaborating with Weird Al on one of the aforementioned “Epic Rap Battles of History” was a career highlight; he was and is a hero of mine.

One time I saw Orlando Bloom having coffee at the Oaks and thought it was pretty cool. And finally, I literally live in Hollywood.

I’ve severed all contact with my family and friends back home now that I’m a big L.A. hotshot/Scientologist.

What tip would you give to any comedian who moves here?

Only one tip?! OK, fine, I’ll restrict myself to just a single piece of advice, which I’ll offer in four parts.

1. Make things and stay in touch with people. You never know which old friend is going to stumble across your YouTube channel and invite you to perform comedy on their TV show, or get a TV show and hire you to do audience warm-up for it, or create a hit web series and give you a job as a writer. Those are all things that have happened to me that I wasn’t expecting, and they’ve been some of my favorite career opportunities.

2. Listen to KDAY 93.5, Los Angeles’s amazing old-school hip-hop station.

3. Ultimately, life is to some extent beyond our control, so work hard on making and doing things that provide you with creative juice and joie de vivre while attempting to be happy independent of how much you achieve showbiz-wise.

4. Get a bike and ride it to any destination that’s less than four miles away. L.A. has flat, wide streets, almost no rain, and motorists who are comparably respectful to those in other cities, despite what you hear. Also, cycling keeps you alert and engaged and reduces time spent sitting in traffic jams. But it also gives you less time to listen to KDAY on your car radio. Everything’s a trade-off!

Where do you see yourself five years from now?

In five years, I’d like to be in a place where I have a great answer to this question, which I never do. I hope to continue to do the many wonderful things I’m currently doing, just on a grander scale: releasing more mixtapes and albums of music, continuing to raise the bar on music videos by making more of them with more ambitious concepts and bigger budgets; doing better-paid live shows for larger crowds who show up in increasing numbers specifically to see me; doing more audience warm-up for TV shows, which I find very fun; getting hired for increasingly cooler and more lucrative freelance and non-freelance writing gigs; and continuing to learn and find new creative endeavors I like doing onstage and off. It would be fun to take on the challenge of releasing an album and/or doing a late night set that’s all stand-up – no music. I’d like to create a television show with my friends, and I’d REALLY like somebody to create a part just for me in their TV show. (Take notice, friends!) But like I said earlier, many of the accomplishments that have brought me the most attention and/or money and/or creative satisfaction have fallen in my lap in ways that I couldn’t have anticipated. So between now and five years from now, I’ll be working away at the short- and medium-term projects and goals that I can currently perceive clearly, and looking forward to the unforeseen opportunities that wind up presenting themselves.

Zach Sherwin’s first full-length album, Rap!, is out now. Buy it via iTunes or Amazon here:

Zach Sherwin’s brand-new podcast with Myq Kaplan, “Words of the Years,” is available now on the also brand-new Howl platform. You can also check out his music videos and more via YouTube at youtube.com/zachsherwin.

Is there a comedian in Los Angeles that you’d like to see me style and profile for another installment of Going Hollywood? Send your nominations to: thecomicscomic AT gmail DOT com

Sean L. McCarthy

Editor and publisher since 2007, when he was named New York's Funniest Reporter. Former newspaper reporter at the New York Daily News, Boston Herald and smaller dailies and community papers across America. Loves comedy so much he founded this site.

View all posts by Sean L. McCarthy →

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