Quentin Tarantino originally wrote the role of Mr. Pink for himself. Steve Buscemi originally auditioned for the part of Mr. White. Michael Madsen originally auditioned for the part of Mr Pink. George Clooney read for the role of Mr. Blonde/Vic Vega but was turned down, and Christopher Walken refused the same role. Vincent Gallo turned down the role of Mr. Pink. Samuel L. Jackson auditioned for the role of Mr. Orange. Once Tim Roth was cast, Quentin Tarantino originally wanted him to play Mr. Blonde or Mr. Pink. Robert Forster and Timothy Carey auditioned for the part of Joe Cabot, and the film is dedicated to Carey.
Mr. Blonde's real name is Vic Vega. This is the same surname as Vince (John Travolta) from Quentin Tarantino's other film, Pulp Fiction. Tarantino has revealed that are Vic and Vince brothers. He also intended to do a prequel to both films called "Double V Vega", which would star the Vega Brothers, but Madsen and Travolta eventually got too old to reprise their roles, and Tarantino has since abandoned it.
Michael Madsen had difficulty filming the torture scenes. He was particularly reluctant when he was required to hit actor Kirk Baltz. When the cop, pleading for his life, says that he has a child at home (a line not in the script), Madsen, himself a new father at the time, was so disturbed by the idea of leaving a child fatherless that he couldn't finish the scene.
The film's budget was so low that many of the actors simply used their own clothing as wardrobe; most notably Chris Penn's track jacket. The signature black suits were provided for free by the designer, based on her love for the American crime film genre. Steve Buscemi wore his own black jeans instead of suit pants.
Madonna - who is the main topic of the opening conversation - really liked the film but refuted Quentin Tarantino's interpretation of her song 'Like a Virgin'. She gave him a copy of her 'Erotica' album, signed "To Quentin. It's not about dick, it's about love. Madonna."
Quentin Tarantino wanted James Woods to play a role in the film, and made him five different cash offers. Woods' agent refused the offers without ever mentioning it to Woods as the sums offered were well below what Woods would usually receive. When Tarantino and Woods later met for the first time, Woods learned of the offer and was annoyed enough to get a new agent. Tarantino avoided telling Woods which role he was offered "because the actor who played the role was magnificent anyway". It is widely accepted that the role that Tarantino was referring to was Mr. Orange.
In Mr. White's flashback, Joe asks him about a girl named Alabama. This is a reference to Patricia Arquette's character from True Romance. Quentin Tarantino has stated that he originally intended this character to meet up with Mr. White and to become partners in crime. When "True Romance" was released a year after this film, the ending was changed and so this backstory became inconsistent because Alabama never went on to meet up with Mr. White.