The protagonist and host of the retrospective special. He is deeply disturbed by a vivid dream about his past life as a Vermont innkeeper, leading his loved ones to diagnose a mid-life crisis. Despite their reassurances, he remains confused upon encountering characters from the dream at the end.
Darryl appears alongside Larry, compounding Bob's existential confusion at the elevator.
Larry appears as a lingering dream character that disrupts Bob's perceived reality.
Jerry provides professional psychological assessment and validation for Bob's dream.
Howard acts as a close friend who shares personal vulnerabilities with Bob.
Carol serves as Bob's dedicated receptionist, maintaining his daily office routine.