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The Crossword Show with Zach Sherwin on Tour

2022 Crossword Show Key Art v2.jpg




JULY 14 - 3S Artspace | Portsmouth, NH | TICKETS

JULY 15 - Frontier Theater | Brunswick, ME | TICKETS

JULY 16 - WBUR CitySpace | Boston, MA | TICKETS

JULY 18 - Shea Theater | Turners Falls, MA | TICKETS

JULY 19 - Caveat | New York, NY | TICKETS

JULY 20 - Caveat | New York, NY | TICKETS

JULY 21 - Arlington Drafthouse | Arlington, VA | TICKETS 

Zach Sherwin, a Los Angeles-based comedian and writer known for his work on Crazy Ex-Girlfriend and Epic Rap Battles of History, is bringing The Crossword Show back to the East Coast, with stops in familiar cities like Boston and New York as well as first-time markets around New England and in Arlington, VA. Fresh off a batch of packed shows in Austin, TX at the Moontower JFL Comedy Festival, The Crossword Show is excited to return to East Coast stages for the first time since a sold-out run in March 2020 with a brand-new puzzle, amazing guest solvers, and the usual mind-bending array of comedy, music, wordplay, and trivia.


The Crossword Show is a live comedy performance hosted by Zach Sherwin in which a panel of celebrity guests solves an actual crossword puzzle onstage in front of an audience, with everything displayed on a big screen so the crowd can follow along. The Crossword Show is co-produced by Zach Sherwin and Blonde Medicine, a Bay Area based record label and production company run by Dominic Del Bene and Jessica Mozes.


Past guest solvers include: Mayim Bialik, Jon Lovett, Aparna Nancherla, Lisa Loeb, Pete Holmes, Janelle James, Lauren Lapkus, Josh Gondelman, Joyelle Nicole Johnson and many more!


Zach collaborates with a different New York Times-published crossword maker to create each puzzle, and then escorts a panel of guest comedians (or musicians, actors, academics, radio personalities, and even local politicians) through the process of solving it.The clues work like the ones in a regular crossword puzzle, but they’re also rhyming rap lyrics: there’s an Across Clues rap and a Down Clues rap over the course of each show. As the solvers progress through the puzzle, Zach performs material - comedy, music, trivia quizzes, deep dives, etc. - unlocked by the various answer words. All of these words and themes begin to connect in increasingly mind-blowing ways, and the grand finale is one last musical number that incorporates all of the answer words from the solved puzzle and ties everything together. And, of course, there’s lots of riffing and banter with the panelists. No crossword expertise is required to be dazzled by this unique and joyful experience!


Guest solvers will be announced soon.



Zach Sherwin is a Los Angeles-based comedian and musician. He is the creator and host of The Crossword Show, in which a celebrity guest panel solves a crossword puzzle live onstage in front of an audience. The Crossword Show has toured the East and West Coasts, including appearances at SF Sketchfest and the American Crossword Puzzle Tournament. In February 2022, Zach published his first crossword puzzle in the New York Times.


Since 2011, Zach has also written for and performed with the popular web series Epic Rap Battles of History. His writing for the show has received numerous Streamy Awards and Emmy nominations, and the videos in which Zach has 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 Problematic with Moshe Kasher (Comedy Central) to MAD Magazine. 


As a solo artist, Zach has released several albums of comedy and music, toured extensively on the college entertainment circuit, worked as an audience warm-up comic on various TV shows, and performed on Totally Biased with W. Kamau Bell (FX) and The Pete Holmes Show (TBS), both long canceled, as well as America’s Got Talent (NBC), which seems like it’s doing great! 



Blonde Medicine is a record label and production company based out of the San Francisco Bay Area. With roots in comedy and music production, they aim to help Artists make great art, no matter what form it may take.Their genre-spanning releases can be found at


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