When Robert De Niro first got a hold of the script he wanted to play the role of Max Cherry. Quentin Tarantino wanted to work with De Niro but had his heart set on Robert Forster as Cherry, so he gave the role of Louis to De Niro.
Quentin Tarantino met Robert Forster in a restaurant and handed him the script, saying "You're going to do this, and that's all there is to it". Forster was naturally thrilled, having had a major career slump. This film saw him come back in a big way, even landing an Oscar nomination.
Spike Lee publicly criticized Tarantino for the frequent use of the word "nigger" in the film. Samuel L. Jackson, previously a frequent Lee collaborator, defended Tarantino in the press. Miramax chairman called Lee in an attempt to mediate between him and Tarantino but Lee refused to speak with Tarantino.
Pam Grier didn't expect her long-time friend Sid Haig to play the judge. She started to burst out laughing as she was surprised by Haig because they both starred together in a number of exploitation films, which this film's style was influenced by.
In the closing credits, Tarantino gives special thanks to "Bert D'Angelo's Daughter" (among others). In the late 70's, Paul Sorvino starred in a TV detective show, Bert D'Angelo/Superstar (1976). Thus "Bert D'Angelo's Daughter" is Paul's daughter and Tarantino's girlfriend, Mira Sorvino.
When Ordell Robbie first goes to Max Cherry's office and is asked if he has the cash for the bond, he responds "I got it right here in my brand new raptor bag." Although the logo is partially obscured, it is clearly that of the Toronto Raptors. Actor Samuel L. Jackson was frequently courtside at Toronto Raptor games the season before filming Jackie Brown.
Louis and Ordell first appeared in the Elmore Leonard novel The Switch. At age 15 Quentin Tarantino was arrested for shoplifting this book, his one brush with "real" crime. In The Switch, Louis and Ordell kidnap a millionaire's wife only to discover he doesn't want her back, a plot that was used in Ruthless People (1986). In the novel's sequel, Rum Punch, Louis and Ordell complain that the movie producers stole their idea (without mentioning the movie by name).
When Ordell first meets Max Cherry in his office, clearly visible beyond Max's desk is a large poster for Ringling Bros. and Barnum & Bailey Circus for which Robert Forster's father, Robert Wallace Foster, Sr., once worked as an elephant trainer.
The inn where Ordell and Louis have a drink is called The Cockatoo Inn. The neon light letters a-t-o-o are out, so it spells The Cocka Inn: cocaine. A hint to the bags of cocaine found in Jackie's bag in the beginning of the movie.
According to Quentin Tarantino, 70's actress Carol Speed originally helped out in making this film and was willing to play a small cameo part in the film. At the last minute, Tarantino decided not to use her in the film.
During the interrogation scene where Jackie is taken into custody - Det. Dargas stated that anyone in possession of over $10,000 should declare it to U.S. Customs - this is based on the regulations coded by the Internal Revenue Service. It is against IRS regulations for an individual to carry over $10,000 in currency (in this case, a cash transaction) without reporting it to U.S. Customs when entering the United States. This is codified under Federal Law under 31 U.S.C. 5316 and Treasury Department regulations (31 CFR Chapter X) - individuals who enter the United States with over $10,000 in cash (or other monetary instruments e.g. stocks, bonds) must file a FinCEN 105 document. FinCEN is the Financial Crimes Enforcement Network, which is a division of the Department of the Treasury.