Book:
- Write Who You Know: Chabon has said that Grady is at least partially based on novelist Chuck Kinder, one of Chabon's college professors who was also reported to have been working on a long, long book that became more than 3000 pages long (Kinder later released a heavily slimmed-down version of it as Honeymooners: A Cautionary Tale).
Film:
- Acclaimed Flop/Box Office Bomb: Despite garnering terrific reviews, it only made $34 million against a budget of $55 million.
- Playing Against Type: Michael Douglas, best known for playing alpha white males in movies like Wall Street, Basic Instinct, and The Game (1997), here plays the pot-smoking, unkempt Grady Tripp.
- Those Two Actors: Katie Holmes and Tobey Maguire had previously appeared together in The Ice Storm.
- What Could Have Been:
- Jerry Goldsmith was approached and slated to write the score's musical score, but scheduling conflicts with The 13th Warrior, The Mummy (1999), and Reindeer Games did not let him reunite with Curtis Hanson, with whom he worked on The River Wild and L.A. Confidential, in which he also received an Oscar nomination for best original score.
- Rob McElhenney was cast as a student at the university who was going to be a minor character and a love interest to Hannah, but that subplot was completely cut in post-production. His character is effectively a Deleted Role, except for one brief appearance when he is seen sitting next to Hannah near the end of the movie.
