'The Crossword Show With Zach Sherwin' Gets Down, and Across, at ArtsRiot | Comedy | Seven Days | Vermont's Independent Voice

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'The Crossword Show With Zach Sherwin' Gets Down, and Across, at ArtsRiot

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Zach Sherwin - COURTESY OF TROY CONRAD
  • Courtesy Of Troy Conrad
  • Zach Sherwin

Zach Sherwin has built a career on wordplay. The Los Angeles-based comedian, writer and musician revels in witty puns and sly double entendres. That's evident from his standup, his three comedic hip-hop albums, and his work on the CW show "Crazy Ex-Girlfriend," on Comedy Central's "Problematic With Moshe Kasher" and for Mad magazine.

Sherwin also writes for and performs on "Epic Rap Battles of History," a hugely popular web series that's pretty much exactly what it sounds like. Famous figures of pop culture and history square off, 8 Mile-style, in rap battles: Alexander the Great versus Ivan the Terrible; Frederick Douglass versus Thomas Jefferson; Oprah Winfrey versus Ellen DeGeneres; Ronald McDonald versus the Burger King.

His latest project perhaps best fuses Sherwin's affinities for comedy, rap and the sheer, geeky joy of a good turn of phrase.

"The Crossword Show With Zach Sherwin," which comes to ArtsRiot in Burlington on Sunday, March 8, is a live game show in which contestants solve a crossword puzzle onstage in real time in front of a live audience. Past contestants have included comics Rachel Bloom, Aparna Nancherla, Emily Heller and Josh Gondelman, as well as actress Mayim Bialik, musician Lisa Loeb and many others.

At ArtsRiot, guests will include nationally touring comic Kyle Kinane, Vermont Comedy Club co-owner Natalie Miller and Burlington City Councilor Ali Dieng (D/P-Ward 7) — who, according to Sherwin, is the first public official to do the show.

"That's something we've always wanted to try but haven't," Sherwin says in a phone interview with Seven Days.

He concedes that watching other people, even comedians, solve a crossword puzzle might not seem like a recipe for hilarity. "It's more fun than it sounds," he insists.

For one thing, Sherwin writes the clues for the puzzles himself. Though designed to function like normal crossword clues, they're also rhyming rap lyrics. A past puzzle included the following clue: "Capital that's not in Czechoslovakia but is in 'Czechoslovakia,'" four letters. A subsequent or preceding clue would rhyme, somehow, with "Czechoslovakia," forming a lyrical couplet. (The answer, by the way, is "Oslo.")

All of the across clues compose one rap, the down clues another. As a preview before the puzzlers begin solving, Sherwin performs each rap with an accompanying music video.

But there's more. Every solved clue launches the contestants down a comedic rabbit hole, with results that Sherwin likens to "pub trivia inspired by whatever word they got right."

If the correct word is, for example, "pelican," the panel will riff on pelicans while Sherwin, with the aid of a slide show, offers factual tidbits about the long-beaked water birds alongside off-the-cuff jokes.

"It's kind of informative, and you might even learn something you didn't know about pelicans," Sherwin says.

"There's no other show like it that I'm aware of," says Miller, who was a contestant when Sherwin brought the show to ArtsRiot last year, along with Burlington expat comics Aaron Paulsen and Tina Friml. "It's hard to find things in comedy that haven't been done before and that are done really well, and Zach's done that."

For all his varied talents, Sherwin is not a puzzle maker, so he teams up with people who are — they're known as "constructors" in the crossword biz. The Burlington show is based on the fourth puzzle Sherwin has devised, each with the help of a different constructor. Collectively, Sherwin's collaborators have published in everything from the New York Times to hip indie publications.

For each puzzle, the constructors choose all the words, typically tying them together with a theme, and send Sherwin a completed grid. Sherwin then writes all the clues, with input from the constructors.

"I check in frequently," Sherwin says, both to make sure the answers are fun and "to make sure I'm not breaking the conventions of crossword clueing."

Sherwin comes from a wordy family. His mother was a rabbi, and he credits the "sacred wordplay of the Torah and the Talmud" with instilling his appreciation for acrostics. He grew up solving newspaper jumbles with his grandfather and the occasional crossword puzzle with his grandmother.

He is not, however, a lifelong crossword enthusiast. Sherwin says he started regularly doing the puzzles only recently, as his show took shape and he felt the need to speak the rather particular language of crossword.

"I had written all of show No. 1 before I started doing the New York Times puzzle," Sherwin confesses. While he now does that puzzle daily, crossword is still more pastime than passion. "I like crosswords, but I'd be hesitant to upgrade it to love," he says.

Sherwin stresses that being a crossword whiz isn't a prerequisite for panelists.

"If that lights you up, great. Have at it," he says. "But, to me, it's all about the comedy and the connections and the music and the wordplay. I don't care that much about the game."

An equally good, if not better, way to play, according to Sherwin, is to have no idea what you're doing.

"We've found that there's so many different ways to play our show," he says. "We've had people who've been like, 'I've never done a crossword puzzle. I'm an idiot' ... and it works out great."

Likewise, knowing a three-letter word for an Egyptian cobra (asp) or a five-letter word for a Greek muse (Erato) isn't mandatory for audience members.

Zach Sherwin - COURTESY OF TROY CONRAD
  • Courtesy Of Troy Conrad
  • Zach Sherwin

"I'm not just saying this because I want people to come: You do not need to be a crossword enthusiast to enjoy what's happening on the show," Sherwin says. "The crossword part is really just a platform for all of the other stuff to happen on."

Miller, who is a crossword enthusiast, agrees.

"Do you have to do crosswords to be able to play 'Wheel of Fortune'? No," she says. "The most entertaining thing about the show is all the riffing and in-between stuff. Solving the puzzle is just how you get there."

"I never want people to feel dumb. I want to avoid that at all costs," Sherwin continues. "And crossword puzzles make people feel like they're gonna feel dumb. So I think it's great when a solver is like, 'I really have no idea what's going on here.' I think it puts the audience at ease, like it's OK to have your head spinning a little bit."

"The Crossword Show," which Sherwin coproduces with LA comedy producer Dominic Del Bene, draws frequent comparisons to another game show in which jokes are more important than right answers: NPR's weekly news quiz "Wait Wait ... Don't Tell Me!" Sherwin embraces that analogy, but he has no plans to develop his show for radio or podcasts. "We're pretty convinced it's a visual experience," he says. "So we think it's a TV show, and we're eager to see if and when that comes about, how we'll adapt it for that."

If he does spin "The Crossword Show" into a TV or web series, it's not hard to envision it finding an audience, just as "Epic Rap Battles of History" did. Sherwin sees a connection between those two projects that goes beyond silly raps.

"I am convinced that, for me and for a lot of people, it's so good to have something that comedy can bounce off of," Sherwin explains. In the case of "Epic Rap Battles," that means pairing the dry history we all know with the unexpected element of funny hip-hop.

He believes "The Crossword Show" offers a similar juxtaposition.

"The words are there; we know the black-and-white grid; it's kind of stark and severe," Sherwin says. "But to see it open up in this new way, to get these new doors and windows into it — it's just doubly exciting."

Much like rapping about Ben Franklin's wooden teeth, he adds, infusing comedy into crossword puzzles "enlivens the material in a whole new way."

The original print version of this article was headlined "Word, Nerd | "The Crossword Show With Zach Sherwin" is a 31-letter phrase for puzzling hip-hop hilarity"

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