The house where Billy Brown's parents live in the film is the very same house where Vincent Gallo lived with his parents growing up.
Christina Ricci and Lance Acord both had difficult working relationships with Vincent Gallo resulting in Gallo publicly disparaging them after the film's release, calling Ricci a "puppet" and overweight and Acord a "button pusher". Anjelica Huston also did not get along with him, and Gallo claimed Huston caused the film to be turned down by the Cannes Film Festival.
Original cinematographer Dick Pope was fired during preproduction for opposing Vincent Gallo's decision to shoot on reversal film. Gallo intended to act as cinematographer himself but the bond company insuring the film would not allow it. Gallo then hired Lance Acord, who was at the time a non-union cinematographer who had never shot a feature.
Kevin Corrigan originally turned down the role of Goon because he was uncomfortable with it. He later changed his mind and asked for the role back. Gallo had hired another actor to play the role but fired him and re-hired Corrigan. After filming, Corrigan was still uncomfortable with his performance and asked to be uncredited.
Mickey Rourke was going through tough times with both career and finances. According to an interview Rourke stated that Gallo offered him a small part on the movie and paid him with a paper bag containing $100,000
The song Billy's father sings to Layla, "Fools Rush In Where Angels Fear To Tread", was actually sung by Vincent Gallo's father, Vincent Gallo Sr.
Gallo decided to shoot on reversal stock (the equivalent of color transparency film - expensive both to buy and process), without even knowing if the stock was available in 35mm or if any labs were capable of developing it.
Although Lance Acord was widely credited with the film's distinct visual style Vincent Gallo has claimed credit for designing most of the film's cinematography. He also publicly disparaged Acord, saying "This guy had no ideas, no conceptual ideas, no aesthetic point of view."
Ben Gazzara ad-libbed the part where he shoves his face between Christina Ricci's breasts at the dinner table.
Anjelica Huston and Christina Ricci had previously co-starred as Morticia and Wednesday Addams in The Addams Family (1991) and Addams Family Values (1993).
The dinner scene with Billy's parents pays homage to the static visual style of Japanese director Yasujirô Ozu, who is referred to by the OZU on the license plate of Layla's car.
The character Scott Woods is a reference to Buffalo Bills place kicker Scott Norwood who missed the game winning field goal in Super Bowl XXV.
A piece of Billy Brown's dialogue can be heard playing backwards in the song "I'm Getting Closer" by M83.
Included among the "1001 Movies You Must See Before You Die", edited by Steven Schneider.
When Billy (Vincent Gallo) tries to drive Layla's (Christina Ricci) car, he discovers that it is a stick shift (manual transmission) and gets annoyed because he doesn't know how to drive a stick shift. Ironically, Ricci didn't know how to drive a stick shift and kept stalling the car during takes and Gallo got very annoyed with her.