Zach Sherwin’s Live Jew-ish Crossword/Rap Shows

July 31, 2019

Since moving to Los Angeles from Boston in 2010, comedian and writer Zach Sherwin has made his mark performing comedy raps at stand-up comedy venues throughout the United States.

The 39-year-old has written for almost every episode of the web series “Epic Rap Battles of History,” appearing in 10 of them playing historical and pop cultural figures including Albert Einstein, Stephen Hawking and Sherlock Holmes. Between his own comedy rap videos and “Epic Rap Battles,” his work has been viewed over 400 million times.

He also has performed on “America’s Got Talent,” “The Pete Holmes Show” and “Totally Biased with W. Kamau Bell” and written for “Crazy Ex-Girlfriend” and Mad magazine. 

The son of a rabbi, he has taught Hebrew school and is deeply connected to his Jewish identity. His new interactive comedy, music and trivia stage production, “The Crossword Show,” features three guest panelists solving a crossword puzzle live onstage. The puzzle is projected on a screen so the audience can follow along and the clues are written as raps. Audience members at “The Crossword Show” (the latest puzzle debuts at the Dynasty Typewriter stage near MacArthur Park on Aug. 7) can expect etymology and linguistics lessons, a crash course in the history of rap and hip-hop, and various Jewish references. 

Jewish Journal: How was “The Crossword Show” born? 

Zach Sherwin: Will Nediger constructed dozens of crossword puzzles for The New York Times. He reached out online in the summer of 2017 to tell me he liked the wordplay in my tweets and suggested we find a way to collaborate. I said, “What if you create a crossword puzzle and I write clues that are also rap lyrics?”

As it started coming together, we had no idea what we were going to do with it but I began to get more excited about it and mentioned the project to comedy producer Dominic Del Bene, now my partner on “The Crossword Show.” Dominic said, “Let’s release this together as a vinyl EP with the grid on the front cover and the clues printed on the back and the clue raps on the record. You can sell it at shows.” 

When I told another friend about it, he said, “Wait, this is totally a live show where guests solve the crossword onstage, like [the NPR show] ‘Wait Wait … Don’t Tell Me.’ ” The first show was in November 2018 and took about a year and a half to figure out. The second one took three months, the [upcoming] puzzle three to four months. I want the show to be bristling with delightful things.

JJ: How do you find the guest panelists?

ZS: I heard a crossword podcast that mentioned [musician] Lisa Loeb had co-authored a guest crossword [for the Times in 2017]. We had a good interaction on Twitter and I had a sense she’d be down to do it. She set a high bar for future guests to clear.

JJ: Your shows often have Jewish references. Does this happen organically or is it a conscious choice?

ZS: It’s organically coming out as I work through the material and try to find creative things to do at every possible point. I’m really glad I have a Jewish background. The religion is so wordplayish. The universe was created with an act of language. Talmudic and rabbinic thought is informed by words, letters and acrostics. There’s a concept that each letter is imbued with holy specific significance. No question, this is the religion to have grown up in in order to do “The Crossword Show.” 

JJ: How did you become interested in language to such an intense degree?

ZS: I come from a bookish family. Wordplay and puns. Some of my earliest memories are with my grandpa doing the Jumble in the newspaper. [As an adult] I became aware of a whole subculture of word magicians — people who do crazy stunts with words and letters. There’s a fine line between being too geeky and being interesting to almost anyone if pointed out in the right way. I kind of feel that’s my role in the show, [to create an] appreciation for how these things — comedy, rap, words, Judaism — can be woven together and be interesting. I want to bar mitzvah tutor the crowd through it. Let me show you why it’s fun.

JJ: You also co-wrote “Crazy Ex-Girlfriend’s” “JAP Battle Rap,” which has an insane number of Jewish insider references including “you got me trippin’ like Birthright” and “we were egged on like seder plates.” How did this song end up on TV?

ZS: [Show creator] Rachel Bloom and I were musical comedy scene friends before she had the show. I texted her my congratulations on the show and she wrote, “Dude, I’m bringing you in to write for it.”
And man, did she come through. There was a nice click, especially on “JAP Battle,” with the team over there. They told me they wanted Jewish references. I thought I’d really go for it and if they want to dial it back later, they can. I’m astonished it made it on TV with all those jokes in it. 

JJ: How has your comedy evolved over the years? 

ZS: I did debate in high school. I didn’t like the research but I liked getting to talk as performance. In college, I co-founded a comedy group and after an amicable breakup, I started doing comedy raps. Like with Judaism, the thread with hip-hop is it’s so language-y. Rappers are huge punsters and wordplayers. I definitely absorbed all of that. I was feeling stalled out creatively until “The Crossword Show.” It’s the love of a lifetime. I feel incredibly fortunate. This project lights me up 100%.

For more information about “The Crossword Show,” visit his website. 

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