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!

You may also like the following events from WBUR CitySpace:

• Next Monday, 15th September, 06:30 pm, Curated Cuisine: Dip to dinner with ‘Salsa Daddy’ author and chef Rick Martinez in Brookline
• Next Wednesday, 17th September, 07:00 pm, WBUR Member Night: Behind the scenes of On Point with Meghna Chakrabarti and Jonathan Dyer in Brookline
• Next Friday, 19th September, 07:00 pm, New York Times Games night with Everdeen Mason in Brookline

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