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 accidentally loses a significant amount of money and it falls in the hands of the students. As Principal Durbin and Helen investigate who stole the money, the students and teachers admit to other wrongdoings.

Mr. Pugh plans a field trip for the Toledo chapter of the Ohio Naturalists. When Jack can't write his own book, he agrees to be ghostwrite for popular author Robin Shwank -- only to insert his own chapters into Shwank's book.

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.

Principal Durbin and Helen sweep lockers. Jack finds out that Anthony has been lying about his extracurricular activities. Jack and Lynette follow Anthony to find out what he's really been up to. The search for Stef's baby donor intensifies.

Jack has Mary drive him to the doctor, but a prank results in him getting the same procedure twice. At school, Durbin and Helen embarrass themselves and the kids compete over class superlative titles.

Principal Durbin takes it upon himself to help Jack advance his book with an appearance on Toledo's morning TV show but lets his five minutes of fame get the best of him. The other teachers lead a competition within the Young Entrepreneurs Club.