Because of the way the movie was shot, Mickey Rourke (Marv) and Elijah Wood (Kevin) never met until after the film was released.
The swords used by Miho (Devon Aoki) in this film are the same ones used by some of the Crazy 88 in Kill Bill: Vol. 1 (2003). That film's director, Quentin Tarantino, had been keeping them in the back of his garage.
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 scene in which Marv climbs out of the manhole, and staggers up against a wall, was acted out in reverse, then shown forwards, to give an otherworldly appearance to Marv.
Guest director Quentin Tarantino directed the scene involving Dwight (Clive Owen) and Jackie Boy (Benicio Del Toro) in the front of the car, before Dwight is pulled over by a police officer.
Despite appearing in all three of the major stories, Brittany Murphy filmed all of her scenes in one day.
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.
Robert Rodriguez scored Kill Bill: Vol. 2 (2004) for one dollar. Quentin Tarantino said he would repay him by directing a segment of this movie for one dollar. 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."
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."
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."
"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 complemented the graphic novels.
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 house, because he 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 this film possible, as no other studios would take a chance on either Rodriguez's methods or such a bizarre film.
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.
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.
The shape of Elijah Wood's chin was changed subtly in post-production to give him a more unsettling appearance.
Jessica Alba went to strip clubs as a part of her research for her character. However, she said that it didn't help because all the pro-strippers were doing "is trying to get tips."
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.
Although the majority of the movie was shot against green-screen, there were four practical sets created: - Kadie's bar - Shellie's apartment - Hartigan's prison cell and the hospital in the epilogue.
Leonardo DiCaprio was originally up for the role of Junior but eventually declined the role, which later went to Nick Stahl.
Counting only blows to the head or face, Marv is struck 21 times through the course of the movie.
An obscene pun can be seen on the matchbook found by Hartigan: *Liquor in the front, poker in the rear*.
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.
When Marv visits Lucille's apartment for his medicine, he says, "this isn't some creep with a gas can trying to torch some wino!" This is a reference to the Sin City story "Just Another Saturday Night", in which Marv wreaks havoc on a group of preppy kids who were burning winos alive.
Directors Robert Rodriguez and Frank Miller planned each shot in the movie by using the panels from the original book as storyboard.
The cool detective to which Nancy Callahan refers, 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 P.D. James-written movie Children of Men (2006).
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.
Although several of the actors already looked similar to their characters, some of them underwent make-up and prosthetics to more strongly resemble their Frank Miller-drawn likenesses, including Bruce Willis, Mickey Rourke, Benicio Del Toro, and Nick Stahl.
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 "favorite girl" character in that story. The number is a nod to his wife and frequent collaborator Lynn Varley, whose birthday is March 11th.
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).
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) house. 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, Cardinal Roark (Rutger Hauer), and Kevin (Elijah Wood), as Hauer and Wood were cast after Rourke had shot his scenes.
Robert Rodriguez originally asked Hans Zimmer to score the music, but Zimmer couldn't accept it, as he was in England at the time preparing Batman Begins (2005). Zimmer recommended two of his friends, John Debney and Graeme Revell.
The opening credits were made with some of Robert Rodriguez's choices for the characters before any were cast.
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 seven foot giant while Cardinal Roark is a dwarf. In the Sin City movie, Marv (Mickey Rourke) is two inches shorter, at 5'11" than Cardinal Roark (Rutger Hauer) at 6'1".
With the exception of "The Customer is Always Right," at some point during each segment the narrator says the name of the story as part of the dialogue.
Although the action happens in the fictional Basin City, a replica of New York's Chrysler Building can be seen in the background when Marv is running by the rooftops.
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 (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).
One of the guns used by Hartigan is a Beretta M93R, a gun modified and then used in the RoboCop movies. Frank Miller co-wrote the screenplays for RoboCop 2 (1990) and RoboCop 3 (1993).
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.
The "razor-wire handling" gloves are actually lacrosse gloves called Gladiators made by STX.
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: May 19, 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.
Michael Madsen was briefly considered for the role of Marv before Mickey Rourke was cast. He was eventually cast as Bob.
Uma Thurman, Sarah Jessica Parker, Ashley Judd, Carrie-Anne Moss and Naomi Watts were considered to play Lucille before Carla Gugino was cast.
Rosario Dawson, Mickey Rourke, Bruce Willis, Jessica Alba, Jaime King, and Powers Boothe are the only cast members to eventually return for the sequel to this movie, Sin City: A Dame to Kill For (2014).
Director Robert Rodriguez added the music Jessica Alba danced to later; during shooting, she was listening to different music.
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.
In one scene Gail (Rosario Dawson) refers to Dwight (Clive Owen) as "Lancelot", a knight of the round table of King Arthur. Owen played the lead role in King Arthur (2004).
This marks the fourth film to feature cast members Bruce Willis and Michael Clarke Duncan. They previously starred in Armageddon (1998), Breakfast of Champions (1999) and The Whole Nine Yards (2000). In fact, this is also the former's second collaboration with Elijah Wood after North (1994).
Benicio Del Toro and Josh Hartnett have both portrayed Lawrence Talbot. Benicio Del Toro in The Wolfman. And Josh Hartnett in Penny Dreadful.
Even though their characters had never met, this is the first film that stars Brittany Murphy and Elijah Wood together. The second film is Happy Feet (2006), in which they portrayed a couple.
The film cast includes one Oscar winner: Benicio Del Toro; and three Oscar nominees: Michael Clarke Duncan, Clive Owen and Mickey Rourke.
Both Devon Aoki (Miho) and Jessica Alba (Nancy) have appeared with Paul Walker in different films: 2 Fast 2 Furious (2003) and Into the Blue (2005) respectively.
The song that was featured in Carla Gugino's earlier film, Snake Eyes (1998) was "Sin City" by Meredith Brooks and the song foreshadowed Carla Gugino starring in this film.