“ The joy of live performance is that we’re all experiencing the same thing together and it unites us as a community.”
When I think of crossword puzzles, I think of a quiet, cerebral exercise. It’s often a solitary activity, maybe occasionally yelling out if anyone knows a four letter word for “milk’s favorite cookie.” When Zach Sherwin considered crossword puzzles, however, he thought, okay… but what if it also had comedians, rap, music, and just a little bit of chaos, all wrapped up in an epically funny live show?
Zach Sherwin has long had a way with words. He cut his teeth performing sketch comedy and honing his rapping skills as MC Mr. Napkins. He eventually found his way to Epic Rap Battles of History, which found a way to make nerdy, boring history feel fun and – dare I say – cool.
His love of wordplay and puzzles led him to create The Crossword Show. 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. 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. It is clever, hilarious, and had me awestruck at the mental gymnastics Zach goes through over the course of the show.
Zach joins us on REPOD to talk about how he turned a quiet nerdy activity into something funny, thrilling, and interactive. I really enjoyed hearing him talk about the secret sauce of crafting this show, from how he adjusts the difficulty of the clues, to what makes a live show special. He was a delightful guest.
Are you intrigued by how a live crossword stage show works? Zach will be performing at the Reality Escape Convention in Laval in 2026. This is a show you won’t want to miss.
Thank You to Our Sponsors
We are immensely grateful to our sponsors this season: REA Patreon Backers, PG’s Playhouse, Buzzshot, and COGS. We truly appreciate your support of our mission to promote and improve the immersive gaming community.
Support Room Escape Artist on Patreon
Love escape rooms as much as we do? At Room Escape Artist, we’ve been analyzing, reviewing, and exploring the world of immersive games since 2014. We help players find the best experiences, and push the industry forward with well-researched, rational, and reasonably humorous escape room and immersive gaming content and events.
By becoming a Patreon supporter, you’re not just backing a blog — you’re fueling a mission to make the escape room and immersive gaming community stronger, more thoughtful, and more connected. You can also access exclusive Patreon content such as the Bonus Aftershow, Spoilers Club, and get early access to escape room Tour tickets and REA articles.
Your Patreon support goes toward our mission: paying our contributors, funding our infrastructure, and supporting deep research and industry advocacy.
PG’s Playhouse Podcast
If you love wordplay, puzzles, and trivia, this is the podcast for you! PG’s Playhouse recreates a fun game night with friends, all in a short, 30-minute format. Of course, what’s game night without making new friends? We bring on different guests for the different episodes!
Each episode features a puzzle packed with wordplay and trivia, a short chat with the guest, and a segment exploring an interesting topic. I hope you’ll take a listen and play along with us at PG’s Playhouse.
Buzzshot
Buzzshot is Escape Room Software, Powering Business Growth, Player Marketing, and improving the Customer Experience. They offer an assortment of pre and post game features including robust waiver management, branded team photos, and streamlined review management for Yelp, TripAdvisor, Google Reviews, and Morty. Buzzshot now has integration with the other REPOD sponsors: Morty and COGS.
Special Offer for REPOD Listeners:
REPOD listeners get an extended 21-day free trial plus 20% off your first 3 months, with no set-up fees or hidden charges. Visit buzzshot.com/repod to learn more about this exclusive offer.
COGS
COGS by Clockwork Dog is an easy to use software/ hardware platform for running interactive events, including escape rooms, and other immersive experiences. They have plug & play hardware that seamlessly integrates with their software so you can create a show with lighting and sound cues without having to write a single line of code. Map all kinds of inputs to outputs by building up simple logic steps which determine what you want to happen and when.
Special Offer for REPOD Listeners:
REPOD listeners can get the COGS Starter Set for only $130 + free shipping to the USA. This bundle is usually valued at $257. You can learn more and purchase your Starter Set at cogs.show. Use code REPOD at checkout.
Topics Discussed in this Episode
- 00:00 Sponsor Break: Buzzshot, Escape Room Marketing Software
- 06:24 The Concept of the Crossword Show
- 09:46 The Origin of The Crossword Show
- 15:30 Collaborating with Crossword Constructors
- 18:56 The Crossword Show Experience
- 21:50 Sponsor Break: Room Escape Artist Patreon – Bonus Episodes, Spoilers Club & More
- 23:24 Differences Between the Show and a Normal Crossword
- 27:36 The Makings of a Great Onstage Guest
- 31:36 Aspects of a Good Audience
- 32:42 Sponsor Break: PG’s Playhouse – Puzzles, Pals, and Trivia
- 34:19 The Various Versions of The Crossword Show
- 37:12 Behind the Scenes: Tech and Production
- 39:45 When the Show Has Gone Wrong
- 42:21 Editing and Material Management
- 45:37 Sponsor Break: Cogs By Clockwork Dog, Interactive Show Controls
- 47:12 Origin Story: Becoming a Rapper
- 49:50 The Evolution of Mr. Napkins
- 54:57 Epic Rap Battles of History
- 01:05:16 Zach’s Escape Room Journey
- 01:11:09 Future Plans and Reflections
- 01:15:21 Credits
- 01:17:41 The Escape Room Birthday Kid
Leave a Voicemail
Got a question or thought for the podcast? You can submit a voice recording by calling the Room Escape Artist not-so-hotline that always goes straight to voicemail (551-227-7273).
Resources Mentioned in this Episode
- The Crossword Show Website
- The Crossword Show Mailing List
- Epic Rap Battles of History You Tube
- Mohonk Mountain House Wonderful World of Words
- Preaching Escape Rooms Talk at Mohonk Wonderful World of Words
About Zach Sherwin
Instagram: @zachsherwin
In THE CROSSWORD SHOW, host Zach Sherwin (“Epic Rap Battles of History,” “Crazy Ex-Girlfriend”) presides as a panel of guests 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 clues, Zach takes the show down rabbit holes of comedy, music, wordplay and trivia inspired by the answer words, and everything ties together at the end for a grand finale that’s as satisfying as it is mind-blowing. You don’t need any crossword expertise to be dazzled by this joyful, brainy, one-of-a-kind experience! “Tons of fun.” –New York Times. “Nerdtastic.” –Washington City Paper. “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 Streamy Awards and Emmy nominations, 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 include Crazy Ex-Girlfriend (The CW) and MAD Magazine. As a performer, Zach has appeared on shows ranging from Totally Biased with W. Kamau Bell (FX) to America’s Got Talent (NBC), and he has also worked extensively as a TV audience warm-up comic, including at the last three years of the Scripps National Spelling Bee Finals. In 2025, he published his second crossword puzzle in the New York Times.
Support REPOD
- Subscribe to Patreon for bonus content.
- Please rate and review our podcast!
Thanks for listening!
Support Room Escape Artist’s Mission
There are lots of ways to support Room Escape Artist, like buying from Amazon or Etsy after clicking into the links included in this post or backing us on Patreon.
The money that we make from these helps us to grow the site and continue to add more value to the community that we love so much.
![Mystery Locks – Alchemist’s Box [Review]](https://roomescapeartist.com/wp-content/uploads/2026/01/mystery-locks-alchemists-box-1.jpg)
![PuzzleConnect – Frozen In Time: The Race To Save Christmas! [Review]](https://roomescapeartist.com/wp-content/uploads/2025/12/puzzle-connect-escape-rooms-frozen-in-time-the-race-to-save-christmas-3.jpg)
Leave a Reply