The Crossword Show

Sunday, June 01, 2025 | 7:00 p.m. - 8:30 p.m.

$30 | Friedman Family Auditorium

The Crossword Show returns to Planet Word for its first-ever Washington, D.C. performance of “Puzzle #4: Next Time Won’t You.” Host Zach Sherwin presides as two guest comedians solve a crossword puzzle live onstage, with everything displayed on a big screen so you can follow along. It’s the New York Times crossword meets NPR’s “Wait Wait Don’t Tell Me,” with more rap than you’d expect.

As the solvers decipher the clues, Zach takes the show down rabbit holes of comedy, music, wordplay and trivia, all inspired by the answer words. Everything ties together at the end for a grand finale that’s as satisfying as it is mind-blowing. Whether you’re a daily solver or have never attempted a crossword puzzle in your life, you’ll be dazzled by this brainy, joyful, one-of-a-kind comedy wordplay extravaganza! “Tons of fun.” — New York Times. “Jaw-dropping.” — SFGate.

ZACH SHERWIN is a Los Angeles-based comedian. His writing for the web series “Epic Rap Battles of History” has received numerous Emmy nominations and Streamy Awards, and the Epic Rap Battles in which he’s co-starred have amassed over half a billion YouTube views and an RIAA-certified Gold record. His own YouTube videos have been viewed many millions of times, and his other writing credits range from “Crazy Ex-Girlfriend” (The CW) to MAD Magazine. As a performer, Zach has appeared on “Totally Biased with W. Kamau Bell” (FX) and “The Pete Holmes Show” (TBS), both long cancelled, as well as “America’s Got Talent” (NBC), which seems to be doing a-ok. Zach has also worked extensively as a TV audience warm-up comic, most recently at the 2024 Scripps National Spelling Bee finals, and in 2022, he published his debut crossword puzzle in the New York Times.

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For more information on Zach and The Crossword Show, please visit linktree.com/zachsherwin and www.crosswordshow.com. For questions or concerns regarding accessibility needs, please contact [email protected].