When Jimmy (Samuel L. Jackson) and Sydney (Philip Baker Hall) have their confrontation, Jimmy mentions that he knows Sydney's friends Floyd Gondolli and Jimmy Gator. In Paul Thomas Anderson's next movie, Boogie Nights (1997), Philip Baker Hall plays Floyd Gondolli. In Anderson's followup to Boogie Nights, Magnolia (1999), Philip Baker Hall plays Jimmy Gator.
Philip Baker Hall plays a man named Sydney from Las Vegas who has underworld connections. In Midnight Run (1988), Philip Baker Hall has a small role as a man named Sidney who lives in Las Vegas and is connected to the underworld.
The original shooting script included a different ending for the film where we discover that Jimmy had betrayed Sydney and given his name (and John's and Clementine's) to the man who was being held hostage in the motel. The man tracks down Sydney outside the same highway coffee shop where he met John and shoots him three times, killing him. It's not known whether this scene was ever actually filmed.
Though Sydney's last name is never mentioned in the film, in the original ending the motel man addresses him as "Sydney Brown."
Director Anderson has admitted that Jean-Pierre Melville's _Bob le flambeur (1955)_ was a major influence on this film.
Assistant Cameraman Michael G. Riba turned down 2 weeks of work on Waterworld (1995) - which paid better - to work on Sydney (1996). Riba has been the assistant cameraman on every Anderson film since.
After Paul Thomas Anderson had shown Cigarettes & Coffee (1993) at the 1993 Sundance Film Festival, he was invited to the Sundance Institute Filmmaker Lab. There, he shot a few scenes from this movie (John and Sydney in the diner, John calling Sydney from a payphone, the motel sequence with the hostage, and Jimmy threatening Sydney in his car). John C. Reilly and Philip Baker Hall played the roles they had in the film (John and Sydney respectively), while Moira Kelly played Clementine (played in the movie by Gwyneth Paltrow) and Courtney B. Vance, played Jimmy (later played by Samuel L. Jackson). The diner, payphone and car scenes all got edited and can be seen on the DVD release of the film, but the scene in the motel was not cut.
Paul Thomas Anderson wanted the film to open (the way all of his other films open) with just the production company, "A P.T. Anderson Picture", and the main title, no credits. In order for this to happen, all the members of the cast and crew have to agree to waive their main-credit right. All the cast and crew agreed to this, except producer Robert Jones and so the movie now has beginning credits.
Paul Thomas Anderson's original title for this film was "Sydney". Since it was his first film, and he had basically no control over it (much less final cut, like he's had on his other features since), the studio, Rysher Entertainment, re-cut the film and retitled it "Hard Eight". This obviously enraged Anderson, and through many talks and deals, he convinced the studio to let him release his cut, but with the new title "Hard Eight". Anderson later said this experience taught him that doing your best to make the best possible movie was only "half the job" when being a director. The other half was dealing with all the egos involved.
The screenplay was originally written in 1992, according to Paul Thomas Anderson, in a very short period of time; about 2 weeks.
Paul Thomas Anderson, on the DVD commentary, admitted to successfully pulling off several times the casino rate card trick shown in the film.