The Crossword Show

Monday, October 23, 2023 | 7:00 p.m.

$25 | Friedman Family Auditorium

THE CROSSWORD SHOW makes its D.C. debut this October at Planet Word! Host Zach Sherwin (“Crazy Ex-Girlfriend,” “Epic Rap Battles of History,” MAD Magazine) presides as a panel of guest comedians solves an actual crossword puzzle live onstage, with everything displayed on a big screen so the audience can follow along. As the solvers decipher the various 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 astonishing. You don’t need ANY crossword expertise to be dazzled by this joyful, life-affirming, one-of-a-kind experience!

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 music and wordplay 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. In 2022, Zach published his debut crossword puzzle in the New York Times, and he has also worked extensively as a TV audience warm-up comic, including at the live taping of the 2023 National Spelling Bee finals. For more information on The Crossword Show and on Zach, please visit and