The Crossword Show with Zach Sherwin

The Crossword Show returns to CitySpace for a performance of "Puzzle #3: Cross Country," revamped and turbocharged for 2025. Heads up, regulars: this will be the Boston debut of this particular puzzle and show. Host Zach Sherwin (“Crazy Ex-Girlfriend,” “Epic Rap Battles of History,” MAD Magazine) presides as two guest comedians solve an actual crossword puzzle live onstage, with everything displayed on our screen so you can follow along. It’s like 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, Sherwin 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. You don’t need any crossword expertise to be dazzled by this delightful, brainy, one-of-a-kind experience!

VIP ticketholders will enjoy reserved seating in the front of the theater and access to a 30-minute pre-show experience featuring bonus puzzles and wordplay and a meet and greet.

You may also like the following events from WBUR CitySpace:

• Next Saturday, 22nd November, 11:00 am, ‘Greeking Out’ Live in Brookline
• Next month, 8th December, 06:30 pm, Curated Cuisine: Holiday baking with Dorie Greenspan and Joanne Chang in Brookline
• Next month, 17th December, 07:00 pm, Blue Heron Presents: ‘Christmas in 16th-Century Spain’ concert and conversation with Meghna Chakraba in Allston

Also check out other Comedy events in Brookline, Entertainment events in Brookline.