When Jack is disappointed with the popcorn maker he orders, he and the students plot revenge. Helen goes back to school to get her high school degree and chaos ensues in Principal Durbin's office in her absence.

As the school prepares for winter break, Jack tries to record a lecture on Thoreau's transcendentalism as a way into the University of Wisconsin's philosophy department. Frustrated and unable to finish the video, he falls asleep and has nightmares.

While the rest of the town prepares for the celebration of Toledo's annual Katie Holmes Day, Jack and Marissa plot to ruin the holiday pageant.

Jack's students steal his Harvard pen. Principal Durbin fails the superintendent's inspection.