'''Book''':
* WriteWhoYouKnow: [[WordOfGod 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 [[{{Doorstopper}} 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''':
* AcclaimedFlop[=/=]BoxOfficeBomb: Despite garnering terrific reviews, it only made $34 million against a budget of $55 million.
* PlayingAgainstType: Creator/MichaelDouglas, best known for playing alpha white males in movies like ''Film/WallStreet'', ''Film/BasicInstinct'', and ''Film/TheGame1997'', here plays the pot-smoking, unkempt Grady Tripp.
* ThoseTwoActors: Creator/KatieHolmes and Creator/TobeyMaguire had previously appeared together in ''Film/TheIceStorm''.
* WhatCouldHaveBeen:
** Music/JerryGoldsmith was approached and slated to write the score's musical score, but scheduling conflicts with ''Film/TheThirteenthWarrior'', ''Film/TheMummy1999'', and ''Film/ReindeerGames'' did not let him reunite with Creator/CurtisHanson, with whom he worked on ''Film/TheRiverWild'' and ''Film/LAConfidential'', in which he also received an Oscar nomination for best original score.
** Creator/RobMcElhenney 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 DeletedRole, except for one brief appearance when he is seen sitting next to Hannah near the end of the movie.
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