Trivia: George Clooney (Everett) was going to sing "Man of Constant Sorrow" for the film but his singing voice was very poor so he ended up lip-synching the songs instead. He said "I'm not my aunt [referring to the late singer/actress Rosemary Clooney, best known for her role in "A White Christmas" (1954)]. I decided it would be easier to just do a passionate lip-sync." He was so nervous that the tapes of his singing would get out that he returned to the studio to ensure all the evidence had been erased. The musical director of the film confirmed this but said "George is a very good singer but that style of music is very difficult and one almost has to grow up singing it in order to sing it convincingly. George did a really good version of the tune but it wasn't as good as he wanted."
Trivia: Matthew Perry bet Bruce Willis that if the film would open at the top of the charts in the US (which it did) he would have to guest in an episode of Friends for free (which he did, plus all further episode payments were given to charity).
Trivia: Keanu Reeves was forced into making this movie when his assistant forged Keanu's signature on the script. Rather than a lengthy courtroom battle, Keanu decided to just film the movie. He was also contractually obligated not to speak negatively about the film for a whole year. After the one-year deadline was up. Keanu began trash talking the movie and the circumstance as to why he did it.
Trivia: 13 Mustangs from 1967-1968 were modified to be "Eleanor" in the movie. One was a True Shelby GT500, but this was used by Bruckheimer as a reference piece and used by him personally. The rest were run of the mill Mustangs modified with bodykits and other goodies. One was chopped up to film certain sequences (in car shots, etc.), 2 were destroyed, and the other Mustangs were modified to perform certain tasks (Chases, Jumps, etc.).
Trivia: Gracie's and Vic's hotel room in the movie are both marked 103 for some reason. The crew did it on purpose, for reasons unknown.
Trivia: When Maurice is looking for Trish outside the CD store, you can hear him say, "I'm gonna find your Aaliyah lookin ass." Trish is played by Aaliyah.
Trivia: Not a mistake, but a little extra. When we first see Doug the Head in the bar drinking and getting his lunch, the man on the right, reading the newspaper is director Guy Ritchie.
Trivia: When Tyrone is making mashed potatoes, the prison guard standing behind him is played by the novelist Hubert Selby Jr., on whose novel the film is based.
Trivia: The candy factory name, Jolly Jack, is a tribute to "Jolly" Jack Kirby, a legendary comic book artist and writer.
Trivia: Director Mathieu Kassovitz has two cameo appearances in the film, one as the hooded killer in the doctor's house who shoots at Jean Reno and another as the voice over the CB talking about the Lada car to Vincent Cassel. He was also supposed to have played the role of a policeman in this film but the character was dropped.
Trivia: The 'stain on our country's history' line as Morgan Freeman used in the scalping scene is the same line as Morgan Freeman used in his role in 'lean on me'.
Trivia: The author of the short story this movie is based on (Garrett Murphy) had his name removed from all credits after seeing the movie for the first time. The story has nearly zero visible violence in it, unlike the ultra-violent film version.
Trivia: In the scene where Shaft first calls Rasaan reminding him of owing a favour, the song playing in Rasaan's apartment is one by Sean Paul. Rapper Busta Rhymes (Rasaan) and Jamaican artist Sean Paul have featured on several of each other's songs.
Trivia: The disgusting food that Big Momma makes for Trent and Sherry is exactly the food that is visible being made in the movie "Nothing To Lose", where Martin Lawrence first enters a restaurant with Tim Robbins in the desert at the start of the movie.
Trivia: Ape Boy was actually played by Violent J (who also played Big Baby Sweets). Apparently, because Shaggy 2 Dope was supposed to do a wrestling move on the actor who played Ape Boy, they would have to have someone who was trained in wrestling to play the part. According to Violent J, it would have cost too much money to re-dub someone else's voice over his own in the Doughnut Shop scene, which is why Ape Boy sounds like Big Baby Sweets.
Trivia: Patty Hearst plays Figit's mother which is interesting because the film follows a Patty Hearst kind of situation. A woman is taken hostage by rebels and after a while she joins them. Patty Hearst is a good friend of John Waters.
Trivia: The producer, Luc Besson, makes a cameo appearance as the man whose boat is destroyed by the stray missile. (00:37:35)
Trivia: Rustin Parr shows up in the movie. In the general store there is a man on the floor "fixing" the fridge. He doesn't move in his scenes and seems dead. The only time he speaks is in Chapter 15 after Kim says "Excuse me" and he says "I'm finished now" Rustin Parr was said to have walked into a general store after killing the Burkittsville 7 and saying the same thing. Also "The Secret Confession of Rustin Parr" by DA Sterns shows a picture of Rustin Parr played by the same actor in the movie.