The original writer, Jessica Kaplan, died at age 24 in a small plane crash over Los Angeles' Fairfax district (June 6, 2003), just before filming started. The plane was piloted by her uncle. The film is dedicated to her.
Bijou Phillips and Anne Hathaway refused to do any press or promotions for the film after producers got heavily involved and took the final cut away from the film's female director (Barbara Kopple). This led to the film not being released in theaters.
When Allison is at the police station after the bust on the street, the girl talking to her in cell says, "...then the cop started asking me these really dumb questions, like what's closer to you now, the moon or Europe?" That question was asked to the co-writer of the movie, Stephen Gaghan, when he was detained by drug officers during his battle with drug addiction. The whole story can be found in a Newsweek article written by Stephen Gaghan.
Channing Tatum's stunt double in this movie, Mark Foran, was a very prominent hockey player from Miramichi, New Brunswick, Canada. He can be seen as an extra in many other movies, but mainly does stunt work for Tatum.
A week prior to filming, Anne Hathaway made headlines for an accidental wardrobe malfunction at the premiere of School of Rock (2003). Unbeknownst to Hathaway, the dress she was wearing at the event was sheer exposed her breasts. She later claimed that she "cried about it for days".
The trivia items below may give away important plot points.
The role of Emily was offered to Lindsay Lohan, who turned it down. In an interview, Lohan commented "I got this one script where this girl wants to join a Latino gang and she gets raped. I can't be doing that right now. I don't think that's appropriate."