Room Escape Artist

“Canterbury Tales was basically the precursor to Epic Rap Battles of History.”

The beat drops and freestylin’ rappers take to the stage, battling it out to see who has the best flow. First to the stage is The Knight, and his other contenders are characters like The Wife of Bath, The Miller, or The Reeve. Our topic today is The Canterbury Tales. This is the story of a group of pilgrims who gather around the fire to tell stories, primarily in verse.

Zach Sherwin, our guest today, knows a thing or two about storytelling in verse. He’s a longtime writer and performer on the Youtube channel Epic Rap Battles of History. This show pits two historical characters against each other, battling it out for rap supremacy. Zach has also created The Crossword Show, a hilarious live show where comedians solve a crossword while Zach performs about the topics. He also shares a few puzzles with us today as well.

Today’s game is called Name Dropping, and it’s all about modern names that come from medieval occupations. Grab your tickets to RECON 26 this summer to see Zach perform The Crossword Show live.

Click here for a playlist of Epic Rap Battles featuring Zach Sherwin.

Time Stamps

• 01:12 Game: Name Dropping
• 14:47 Bonus Puzzle from Zach Sherwin
• 18:45 About: Zach Sherwin & Epic Rap Battles of History
• 22:12 Topic: Canterbury Tales
• 32:26 Credits

Check out REPOD Season 10 Episode 10: Comedy, Rap, and Crosswords: The Crossword Show with Zach Sherwin

Guest: 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.

More Podcasts from Peih-Gee & David

If you enjoy PG’s Playhouse, check out Reality Escape Pod (REPOD), where your hosts David Spira & Peih-Gee Law explore immersive gaming from all angles, alongside guests with incredible experience in this realm.

And by supporting Room Escape Artist on Patreon, you’ll get access to the REPOD Bonus After Show ($5 per month and up) and the Spoilers Club ($15 per month and up) where we chat in depth with creators about iconic escape rooms… spoilers and all!

Production Credits

• Hosted by Peih-Gee Law & David Spira
• Puzzles by Peih-Gee Law
• Produced by Theresa Piazza
• Supported by Lisa Spira
• Edited by Peih-Gee Law
• Music by Matt Farthing
• Logo by Theresa Wagner