The lead role was originally offered to Johnny Depp, but he declined due to scheduling conflicts. Joseph Gordon-Levitt later replaced him, despite offers to star in other movies such as Guardians of the Galaxy (2014) and Godzilla (2014). In 2006 when Rodriguez first started putting together ideas for "Sin City 2", he considered Depp for the part of Wallace, the lead character of "Hell and Back", which he was hoping to adapt as one of the film's three segments. The idea to adapt "Hell and Back" was scrapped, however, and Rodriguez chose to adapt "Just Another Saturday Night", "A Dame to Kill For", and the never-published "The Long, Bad Night" instead.
During the seven-year gap between the first Sin City (2005) and the beginning of principal photography on this film, Brittany Murphy and Michael Clarke Duncan passed away, forcing Robert Rodriguez to re-cast their respective roles of Shellie and Manute (Dennis Haysbert). Due to Devon Aoki's pregnancy at the start of production, the character of Miho was also re-cast, with Jamie Chung replacing Aoki. Jeremy Piven also ended up replacing Michael Madsen as Bob.
Dwight McCarthy, played by Clive Owen in the original Sin City (2005), is now played by Josh Brolin before the plastic surgery to change his face that Shellie (Brittany Murphy) mentions in the first movie.
Two of the film's four segments, "Just Another Saturday Night" and "A Dame to Kill For", take place before the first Sin City (2005) film.
Although she played a supporting role in the "A Dame to Kill For" comic book, Frank Miller and Robert Rodriguez retired the character of Shellie from the film version instead of re-casting her, out of respect to the late Brittany Murphy of Sin City (2005).
Eva Green and Marton Csokas played a married couple. They also played a married couple in Kingdom of Heaven (2005). In real-life, the two were in a relationship from 2005 to 2009.
The film's budget was sixty million dollars, making this the most expensive movie Robert Rodriguez has ever directed. This title was previously held by The Adventures of Sharkboy and Lavagirl 3-D (2005).
Two of the film's four segments are based on Sin City comics: "A Dame to Kill For", which ran six issues, and "Just Another Saturday Night", which ran for one. Both comics feature Marv (Mickey Rourke) in a lead role.
The MPAA banned one of the movie's character posters. The poster showed Eva Green as Ava Lord wearing a sheer gown through which her nipple was visible. Green told "Vanity Fair" about the controversy: "I'm not actually naked on the poster. I find it a bit odd. It seems like it's all just publicity, a lot of noise for nothing. You have so many more violent things in the movie business, and this is kind of soft. I'm not naked. It's suggested. I find it really sexy, actually. It's kind of beautiful. But if it shocks people, I don't know what to do about it. I don't want to upset anybody. I don't want to be seen as just the femme fatale or put into some silly box. I hope that people will have enough imagination."
This is the second film adapted from a Frank Miller graphic novel to star Eva Green. She previously starred as Artemisia in 300: Rise of an Empire (2014), which was purportedly adapted from Miller's graphic novel "Xerxes".
DIRECTOR CAMEO (Frank Miller and Robert Rodriguez): When Nancy has the television on in her apartment, the two bums in the show she is watching are played by Miller (writer and honorary director) and Rodriguez (director).
Salma Hayek, Rose McGowan, Angelina Jolie, Rachel Weisz, Michelle Williams, Helena Bonham Carter, Scarlett Johansson, Anne Hathaway, and Jennifer Lawrence were all considered to play the role of Ava Lord before Eva Green was cast.
This is Lady Gaga's second film. Her first was in another Robert Rodriguez sequel, Machete Kills (2013).
Dwight McCarthy's cigarrettes are "Red Apple" brand, most known from Quentin Tarantino's movies. Tarantino is a good friend of Rodriguez's and worked as guest director on Sin City (2005).
In the dancing scene before Nancy talks with the dead John Hartigan, she dances to a song that was also featured in Criminal Minds: True Night (2007). The episode shows Frankie Muniz playing a graphic novelist who creates graphic novels similar to the way the segments in the movie are shown. The episode also includes a Frank Miller quote at the end of the episode.
In an Aug. 2014 interview with Elle magazine, Eva Green was asked if she ever had any trepidation about being naked so much in the movie. She said "Any actor and any actress are very nervous when we have to do that kind of scene. It is not gratuitous [with Ava], the way she uses sexuality to get men and use men is part of her character. But also it's not realistic. It is art. Robert lights it in such a way. He promised me there would be lots of shadows and stuff and things would be added in post. That was very important. But on the day you feel nervous. It's very strange. You're so stressed that it's like, 'I'm not naked. I'm not naked. I'm not naked.' And then you kind of forget that you're naked." She then talked about what she did to prepare for being naked in front of cast and crew. "A lot of actors get drunk. But I was cast a week before shooting so I didn't have time to do much prep at all: So no time to go to the gym. I put myself in the hands of Robert and asked him to remove the cellulite in post-production ... I mean, can you imagine a femme fatale with really bad cellulite? That would be another version of 'Sin City'!" She joked. When asked what she thought about Americans being so prude when it comes to nudity and sex, she replied "It's very subjective. In this movie it's so not pornographic. It's very decent, I think."
Eva Green spent so much of filming in various states of nudity that the promotional poster for the movie featuring the actress was deemed too racy and had to be edited due to the visibility of a nipple.
Jake T. Austin auditioned for the role of Johnny. It eventually went to Joseph Gordon-Levitt.
The film cast includes one Oscar winner: Lady Gaga; and two Oscar nominees: Mickey Rourke and Josh Brolin.
To be grammatically correct, the title should be phrased as "A Dame for Whom to Kill".