- Actor-Inspired Element: The unusual car chase scenes after the kidnapping were Benicio del Toro's idea. He suggested this to Christopher McQuarrie after watching COPS, where a couple of criminals did the same when cops were chasing them.
- McQuarrie also wrote a considerable amount of dialogue for Harold Longbaugh, but Del Toro suggested the "less is more" approach, and had him cut down his lines.
- Box Office Bomb: Budget, $21 million. Box office, $13,069,740.
- Creator Couple: Christopher McQuarrie's wife Heather was the film's costume designer, and she also gave him the idea for the Cesarean section scene.
- Dyeing for Your Art: Ryan Phillippe put on 25 pounds of muscle for the film.
- Executive Meddling: The film is a crime thriller in order to avert this; a friend of Christopher McQuarrie pointed out that after his Oscar-winning work on The Usual Suspects, if he stayed in that genre he would be allowed more creative freedom.
- No Stunt Double: Nicky Katt did most of his own stunt driving.
- Playing Against Type: According to the DVD Commentary, Ryan Phillippe was very interested in doing this movie, as he wanted to avoid being typecast in the type of role that had made him famous.
- Real-Life Relative: Juliette Lewis' father Geoffrey played Abner.
- Spared by the Cut: In the alternate ending, Parker and Longbaugh died, because of their gunshot wounds.
- Throw It In!:
- One scene in the movie shows Juliette Lewis waiting in the van with Ryan Phillippe, who is eating a sandwich. She asks if she can have some, and he shoots her a dirty look before handing half of the sandwich over. This was not originally part of the movie; it was an actual exchange between the two actors while they were waiting between takes. The editor put it into the rough cuts, which was the first time Christopher McQuarrie saw it. He decided to leave it in.
- Ryan Phillippe (much to his horror - he was apologizing for a week after it happened) accidentally hit Sarah Silverman for real while shooting the opening scene and knocked her out. The huge lump on her chin she got from the punch was left in for continuity purposes.
- The smack on the butt Longbaugh gives one of the prostitutes as she passes by was ad-libbed by Benicio del Toro. The actress was reportedly not at all pleased by his improvisation.
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