John Glascott

Principal of William Penn Academy, John Glascott arrives as the steady, sensible adult navigating a school full of eccentric teachers and the perpetually scheming Goldberg family. He runs his office with weary patience, treating each new crisis — parental interference, absurd feuds, hallway chaos — as just another Tuesday.

Tim Meadows plays him with a deadpan calm that works precisely because everyone around him is unhinged; his stillness becomes the joke. The writing lets him underreact to nonsense rather than escalate it, and that restraint, delivered with Meadows's dry timing, makes him a reliable comic anchor amid the show's nostalgic noise.