Jerry owes the library a book that's 20 years overdue and has to deal with Lt. Bookman (Phillip Baker Hall), a library cop who takes his job very seriously. George wonders if a homeless man is his former gym teacher who used to bully him. Kramer starts a relationship with the librarian.
- Asshole Victim: A non-fatal example. Mr. Heyman, who after lost his teaching job, ends up homeless. Though considering how he treated George, it feels well-deserved, especially considering he still hasn't changed in those 20 years.
- By-the-Book Cop: Lt. Bookman, who takes the rules and regulations of the library very seriously and at one point asks Jerry if he's killed anyone.
- Extremely Overdue Library Book: The Tropic of Cancer, which Jerry has owed the library for 20 years.
- Fake Memories: Jerry attempts to clear his good name by seeing his old high school sweetheart Sherry Becker, who he remembers to have a slimmer figure, wore an orange dress, chewed Black Jack gum and they read The Tropic of Cancer. When he meets her, she is broader than he remembers, and said she instead wore a purple dress, chewed Dentyne and instead read The Tropic of Capricorn.
- Sadist Teacher: Mr. Heyman, who loved to bully George and called him the unflattering "Can't-Stand-Ya".
- Static Character: Even after losing his job and being homeless, Mr. Heyman is still the same old Jerkass he was 20 years ago.
- Steven Ulysses Perhero: The library cop is named Lt. Bookman. This is lampshaded by Kramer:That's like having an ice cream man named Cone.
- Wedgie: Mr. Heyman, who gives George one in high school and in present day, give him an atomic wedgie, which breaks off the waistband of his underwear.
- Wham Shot: The copy of The Tropic of Cancer that Jerry owes the library is among Mr. Heyman's possessions.