Robert Rodriguez originally envisioned Johnny Depp in the role of Jackie Boy. Due to prior commitments, Depp could not play the part. While at the Academy Awards, Rodriguez saw Benicio Del Toro with long hair ("Wolf Man" hair, as he describes it. Ironically, Del Toro plays the title character of The Wolfman (2010)) and said that he "was looking at Jackie Boy." He told Del Toro not to cut his hair and mailed him the comic book and a copy of the short, "The Customer is Always Right." Del Toro immediately signed on.
While the three stories in the film are based on "The Hard Goodbye," "The Big Fat Kill" and "That Yellow Bastard" as well as the short "The Customer is Always Right" there is a very brief scene taken from the story "A Dame to Kill For," in which Dwight (Clive Owen) thinks in a voice over in Kadie's Bar how Marv "would have been okay if he'd been born a couple of thousand years ago."
Robert Rodriguez has said that he does not consider this movie to be an adaptation so much as a translation. This is why there is no screenwriting in the credits. The only mention of writing is Frank Miller as the creator of the graphic novels.
"The Customer is Always Right" sequence at the beginning of the film was actually filmed before Frank Miller had completely agreed to let Robert Rodriguez make the movie. Josh Hartnett and Marley Shelton came in and filmed their scenes in one day in front of a green screen in order to show Miller that it could be done in a way that complimented the graphic novels.
Jessica Alba did not know how racy the images of her character Nancy were in the comic until after she signed on for the film. The script originally had several nude scenes for the character, but Alba refused to do any nudity. Robert Rodriguez and Frank Miller didn't think it was important for there to be nudity, so they didn't care.
The film, and many of its effects and scoring, were all done in Robert Rodriguez's studio, which is immediately across the street from his home. Because the director refuses to work anywhere else and shuns other Hollywood traditions, it took his friendship with Miramax honchos Bob Weinstein and Harvey Weinstein to make the production of the film possible, as no other studios would take a chance on either Rodriguez's methods or such a bizarre film.
Robert Rodriguez scored Kill Bill: Vol. 2 (2004) for $1. Quentin Tarantino said he would repay him by directing a segment of this movie for $1. Tarantino, a vocal proponent of film-over-digital, has said that he was curious to get hands-on experience with the HD cameras which Rodriguez lauds. When asked about his experience, Tarantino merely replied, "Mission Accomplished."
According to an interview with "Latino Review", Michael Madsen landed the role of Bob by approaching Robert Rodriguez at the "Kill Bill" wrap party and simply asked why he hadn't been cast in "Sin City." Rodriguez obliged, giving Madsen the only part that hadn't been cast yet: Bob.
Originally Robert Rodriguez didn't plan for Benicio Del Toro to wear make-up, but Del Toro insisted on it. Tarantino later commended the make-up being so good that "people actually forget that's not what Benicio looks like."
On a night between filming days, Robert Rodriguez put on a rock concert at a local nightclub. His own band was the opening act, and the headliner was Bruce Willis and his band, The Accelerators. The concert was attended by Sin City (2005)'s cast and crew, as well as the cast and crew of A Scanner Darkly (2006), which was filming nearby at the same time. All profits from the show were donated to charity.
At one point, Hartigan resists Nancy's advances saying, "I'm old enough to be your grandfather." While Hartigan (age 68) is old enough to be the grandfather of Nancy (age 19), in real life Bruce Willis and Jessica Alba are only 26 years apart in age.
Originally the film was going to include the story featured in the "Sin City" maxi-series "Hell And Back", with Johnny Depp in the lead role as Wallace. This was scrapped before production began but will most likely be filmed for a sequel, as Robert Rodriguez plans to film all of Frank Miller's stories at some point.
The signature white blood proved hard to achieve on screen. Regular movie blood couldn't provide the stark look. The crew had to use fluorescent red liquid and bathe it in black light. In post-production, the liquid was turned white.
As each sequence of this film was shot separately, new cast members were added and incorporated in the stories throughout the production. In many cases separate footage was composited in post-production to look as if it were all shot the same day. For example: Marv (Mickey Rourke) takes Wendy (Jaime King) to Nancy's (Jessica Alba) home. Alba had not been cast yet when Rourke and King shot the scene; her footage was added in later. The same is true of the scenes between Marv and Cardinal Roark (Rutger Hauer) and Kevin (Elijah Wood), as Hauer and Wood were cast after Rourke had shot his scenes.
The cool detective that Nancy Callahan refers to when she says she would sign her letters as "Cordelia" is Cordelia Gray from the novels of P.D. James. Clive Owen (Dwight) starred in the PD James-written movie Children of Men (2006).
In the graphic novel, That Yellow Bastard's car is an Atlantic '57C Bugatti. However, it was changed to a 1936 Cadillac Limo for the film because it would've cost over $230,000 to use the Bugatti for four shooting days. Also, the Yellow Bastard's license plate is "TYB 069." The first half is TYB, the initials for the story "That Yellow Bastard."
In the Sin City comic book Marv is a 7 foot giant while Cardinal Roark is a dwarf. In the Sin City movie the actor playing Marv (Mickey Rourke) is two inches shorter than the actor playing Cardinal Roark (Rutger Hauer).
Robert Rodriguez, who credits Frank Miller's visual style in the comic as being as relevant as his own in the film, insisted that Miller receive a "co-director" credit with him. The Directors' Guild of America would not allow it. As a result, Rodriguez resigned from the DGA, saying, "It was easier for me to quietly resign before shooting because otherwise I'd be forced to make compromises I was unwilling to make or set a precedent that might hurt the guild later on." Unfortunately, by resigning from the DGA, Rodriguez was also forced to relinquish his director's seat on the film John Carter (2012) (at the time "A Princess of Mars" after the book on which it was based) for Paramount. Rodriguez had already signed on and been announced as director of that film when the DGA situation took place, and had been planning to begin shooting soon after wrapping this film.
The cover of the Sin City book "Booze, Broads, and Bullets", can be seen periodically throughout the movie. Its most notable appearance is on the cover of the matchbook that Hartigan picks up to locate Nancy; it is also seen in the background of the strip club in the very next scene as Hartigan first enters (to the right as a poster).
This was one of several films around the world to be shot on a completely "digital backlot" (i.e. with all the acting shot in front of a green screen and the backgrounds added during post-production). While the other movies (Immortal (Ad Vitam) (2004), Sky Captain and the World of Tomorrow (2004), and Casshern (2004) - two of which were shot on film) were shot first, this movie's use of High-Definition digital cameras (like "Sky Captain") in addition to the "backlot" method makes Sin City one of the world's first "fully-digital" live action motion pictures.
One of the hookers in Old Town is dressed like Wonder Woman. She is seen from the back, wearing a set of star-spangled hot pants and with a golden lasso at her side. She also appears in the original comic, in a nearly identical shot (when Marv is asking about Goldie, just before Wendy takes him down).
Both Nancy (Jessica Alba) and Wendy (Jaime King) drive cars with the license plates "LEV 311." Frank Miller often puts this in his various stories for "favourite girl" character in that story. The number is a nod to his wife and frequent collaborator Lynn Varley, whose birthday is March 11th.
When Jackie Boy and his "troops" enter Shellie's apartment, one of them is wearing a t-shirt with a peace sign embedded with a star and flag (the symbol also appears as one of Becky's (Alexis Bledel) earrings). This is the symbol of PAX, the paramilitary peace force from Frank Miller's Martha Washington series of graphic novels, beginning with "Give Me Liberty."
The text of the newspaper shown during "The Hard Goodbye" has a written transcript of the opening scene and "The Hard Goodbye." The author of the article is F. Miller, that is Frank Miller. The date on the paper appears to be either 1993 or 1999, indicating that's when the story takes place.
Footage had been so coveted by fans before its release that when a 27-second behind-the-scenes clip appeared on Entertainment Tonight (1981) (airdate: 19 May 2004), it was quickly (though not officially by the show) placed on the Internet and downloaded over one million times. The raw footage featured only quick shots of Bruce Willis and a scantily-clad Jessica Alba performing in front of green-screen.
Marley Shelton also starred in the 1998 Gary Ross film Pleasantville (1998) which, much like this, employed the same visual technique of showing everything in black and white with only the occasional person, object or scene shown in color.
The strategy used by Dwight to reclaim Old Town by luring the gangsters into a narrow alleyway is based on the strategy used by Spartan King Leonidas to trap the Persian army in the Battle of Thermopylae. The film 300 (2006) was based on a book by Frank Miller about this battle. In addition, the line spoken in Dwight's internal monologue, "No escape, no surrender, no mercy", is spoken by the narrator in "300."
According to Robert Rodriguez's commentary, the scourging sequence between Yellow Bastard and Nancy Callahan was originally shot faithful to the comic book: considerably longer and more graphic than what appears in the final cut or the extended edition. Rodriguez stated that the torture segment was crossing the bounds of bad taste, even for Sin City.
Although the movie is presented primarily in black and white, particular items are in color and, as such, had to be colored blue or green on set. According to Robert Rodriguez, Nick Stahl (who plays Yellow Bastard) was known on set as "The Blue Bastard". Yellow Bastard had to be painted blue because yellow, like green, reacts with the green screen. This causes the color to spill into the background, making them impossible to separate.
The scene that Quentin Tarantino directed is the drive to the pits scene in which Dwight (Clive Owen) talks with a very dead Jackie Boy (Benicio Del Toro). When Tarantino insisted on a real car being built for the shooting Robert Rodriguez told him that it would be easier without one. After shooting a few takes with the real car, Tarantino realized his friend was right. Tarantino also came up with the idea of Jackie Boy's slit throat affecting his speech and Dwight speaking his internal monologue rather than dubbing it in later.
The shot where Hartigan shoots himself in the head at the end is very unlike the way Frank Miller originally made it. It is, however, almost an exact copy of a suicide scene at the end of A Dame to Kill For, part two of the Sin City graphic novels.
Based on the graphic novels "Sin City" (the first graphic novel was just called "Sin City;" this story has been renamed "The Hard Good-Bye" by Miller), "The Big Fat Kill" and "That Yellow Bastard", by Frank Miller. The opening footage with Josh Hartnett and Marley Shelton is from the Sin City short story "The Customer is Always Right" from the "Babe Wore Red" collection. However, the epilogue featuring Hartnett and Alexis Bledel is an original scene written specifically for the movie.