SF Sketchfest 2025

Host Zach Sherwin (“Crazy Ex-Girlfriend,” “Epic Rap Battles of History") presides as a comedian guest panel 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, all inspired by the various answer words. More and more connections emerge as the show unfolds, and everything ultimately ties together for a grand finale that’s as satisfying as it is astonishing. You don’t need any crossword expertise to be dazzled by this brain-tickling, one-of-a-kind experience! With guest solvers Ashley Ray and Matt Walsh.