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.
Mandy Moore and then Kate Bosworth were originally cast as Allison, but Moore dropped out and was replaced by her Princess Diaries co-star Hathaway shortly before filming began. Moore reportedly left the project because she felt uncomfortable with the film's subject matter and nudity. Jena Malone was originally set to play Emily, but left the project shortly after Moore's departure.
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 director (Barbara Kopple). This led to the film not being released in theaters. Richard Roeper of the Chicago Sun-Times claimed that it might have made his list of top 10 films for 2005 had it received a proper theatrical release in the U.S.
New Line Cinema had this screenplay sitting on their shelf for seven years.
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.