The Crossword Show

The Crossword Show is a one-of-a-kind comedy experience created and hosted by Zach Sherwin, the multi-talented writer and performer known for Epic Rap Battles of History and Crazy Ex-Girlfriend. This high-energy variety show blends stand-up, musical comedy, and trivia into a live puzzle-solving extravaganza. As Sherwin leads a rotating panel of guest comedians and musicians through a custom-designed crossword, the audience is treated to a fast-paced journey of wordplay, hip-hop, and deep-dive comedic rabbit holes. Since its debut, the show has become a favorite at prestigious festivals like SF Sketchfest and top-tier venues nationwide. Sherwin’s signature style—meticulously crafted lyrics paired with intellectual wit—ensures that every performance is as brainy as it is hilarious.