Comics
- Development Hell: In the past, Frank Miller has promised several new stories, including a Hartigan prequel, a Jackie Boy prequel, a story set in 1940, and a story set in the Sin City's founding during the Gold Rush. So far, the only new stories written are the two featured in Sin City 2.
- Inspiration for the Work: In a 2016 interview with the Kubert School, Frank Miller explained his inspiration for Sin City thus:I've been a fanatic for a long time for old crime movies and old crime novels. But it started with the movies. And the old Cagney movies. Bogart and all that. I loved just how the morals of the stories are. They're all about right and wrong. But in Sin City in particular I wanted them all to happen to in a world where virtuous behavior was rare, which greatly resembled the world I lived in. It's kinda like the old Rolling Stones song, where every cop's a criminal, and all the sinners are saints, where the lowlifes would often be heroic, and the most stridently beautiful and sweet women would be prostitutes. I wanted it to be a world out of balance, where virtue is defined by individuals in difficult situations, not by an overwhelming sense of goodness that was somehow governed by this godlike Comics Code.
- Writing by the Seat of Your Pants: "The Hard Goodbye" was initially supposed to be just forty pages, but Miller had such a ball making it that it quickly ballooned into something bigger.
- Word of God: According to Frank Miller, Miho and Kevin are supernatural beings. He characterizes them as "demons"; Miho is a good "demon" and Kevin is an evil one.
First film
- Ability over Appearance:
- Cardinal Roark is a dwarf in the book, and Rutger Hauer isn't. Needless to say, he's a One-Scene Wonder and most don't care that he's different.
- Marv isn't just insanely muscular in the comics, but very tall as well, probably close to 7 feet. He tends to tower over almost anyone and can look Manute straight in the eye. Mickey Rourke (5' 11") isn't, but he's the best choice we could have probably had, and even then it required extensive prosphetics to fit Marv's exaggerated facial features.
- Actor-Inspired Element: Jackie Boy's makeup was Benicio del Toro's idea. It was also his idea to have Jackie Boy pry the hands of his gun with his teeth.
- All-Star Cast: The first film alone features Bruce Willis, Clive Owen, Benicio del Toro, Jessica Alba, Rosario Dawson, Mickey Rourke, Elijah Wood, Carla Gugino, Rutger Hauer, Michael Madsen, Michael Clarke Duncan and Alexis Bledel.
- Awesome, Dear Boy: Some of the cast signed on after seeing the test footage which would eventually become the opening scene. In the making-of it's noted that a lot of them had wanted to play Film Noir characters for a long time, such as Bruce Willis. Also, many cast members signed on due to other actors being in talks. Considering the large cast of famous faces, this seems reasonable.
- Cast the Runner-Up: Michael Madsen was briefly considered for Marv before being cast as Bob.
- Channel Hop: The first film was initially distributed by Miramax, as with the other aforementioned franchises, while its sequel is being distributed by The Weinstein Company, but Miramax is co-producing it.
- Completely Different Title: In Iran, the film was called City Crime.
- Creator-Chosen Casting: Mickey Rourke won the role of Marv after one meeting Frank Miller.I was only able to write down one thing - Jesus Christ, he IS Marv!
- Creator's Favorite: Frank Miller has named Miho as his favourite character in the series.
- Dawson Casting:
- Nancy is said to be nineteen years old. Jessica Alba was twenty four.
- Becky is implied to be much younger than the rest of the Old Town girls, possibly still a teenager. Alexis Bledel was twenty four, and only two years younger than Rosario Dawson.
- Fake American: The Englishman Clive Owen played Dwight.
- Playing Against Type:
- Man, it is surprising to see Frodo Baggins playing a mute, psychopathic, cannibalistic Serial Killer.
- Seeing one of the Gilmore Girls as a prostitute.
- Playing Their Own Twin: Scott Teeters as identical twins Lenny and Benny. Likewise, Jaime King portrays both Goldie and Wendy in The Hard Goodbye, thus justifying why Marv would keep confusing the latter for the former.
- Promoted Fanboy: Elijah Wood was a big fan of the original comics, and had previously wondered what an animated series based on them would've been like. Needless to say, he was nothing short of ecstatic when Robert Rodriguez cast him as Kevin in this film.
- Prop Recycling: Miho's swords belonged to the Crazy 88s Kill Bill Vol. 1. Quentin Tarantino, director of Dwight and Jackie Boy's car ride, kept them in his garage and loaned them to the production.
- Real Song Theme Tune: "Cells" by The Servant predates the film and was not specifically made for it. Robert Rodriguez usually composes his own soundtracks, but he felt the song so evoked a Film Noir atmosphere that he used it for the trailer. Ironically, while it's the most well-known song from the film, it's technically not even the main theme.
- Self-Adaptation: Frank Miller was a co-director on the films, as Robert Rodriguez felt that being such a direct adaptation of the original comics (the visual compositions usually being directly lifted from the panels) meant that most of his directorial work had already been done for him by the creator.
- Throw It In!: One of the biggest examples of this trope. Michael Madsen reportedly approached Robert Rodriguez at the Kill Bill wrap party and asked why he hadn't been cast in Sin City yet. Rodriguez then gave him the role of Bob, the only part that hadn't been cast yet.
- Typecasting: Mickey Rourke as an ugly, down on his luck bruiser with a heart of gold? He was born to play Marv. In fact, when Frank Miller met Rourke, the only thing he wrote down in his notes was, "Met Mickey Rourke — HE IS MARV."
- Underage Casting: Hartigan is said to be pushing sixty, then spends eight years in prison. Bruce Willis was fifty at the time.
- Wag the Director: Nancy, as played by Jessica Alba, is always fully clothed (which is not the case for her comic book counterpart) because Alba has a firm policy of never doing nude scenes.
- What Could Have Been:
- Johnny Depp was the first choice for the role of Jackie Boy. But Robert Rodriguez saw Benicio del Toro at the Academy Awards with long hair and immediately knew he was perfect. Adrien Brody auditioned for the role. Depp is, however, still in consideration for the role of Wallace if To Hell and Back is adapted. In fact, the first film was supposed to feature that story, but it was scrapped.
- Leonardo DiCaprio was in talks for the role of Junior. But he eventually declined, and Nick Stahl was cast instead. Steve Buscemi was also considered.
- Adrien Brody and Anthony Michael Hall were considered for Dwight.
- Michael Douglas turned down the role of Hartigan.
- Jessica Simpson auditioned for Nancy Callahan.
- Willem Dafoe and Christopher Walken turned down the role of Senator Roark.
- Ashley Judd, Carrie-Anne Moss, Sarah Jessica Parker, Uma Thurman and Naomi Watts were considered for Lucille.
- 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.
Sin City: A Dame to Kill For
- All-Star Cast: In addition to the returning castmembers, the sequel adds Josh Brolin, Joseph Gordon-Levitt, Eva Green, Ray Liotta, Christopher Lloyd, and even Lady Gaga.
- Box Office Bomb: Budget, estimated between $60 million to $70 million. Box office, $35,093,856. The nine-year gap between the original movie and the sequel, weak reviews and a muddled marketing campaign contributed to this.
- Cast the Expert: Jamie Chung had only a day to prepare for her role as Miho in the second film, but had already undergone weapons and fight training for Sucker Punch and Once Upon a Time.
- Creator Killer: Combined with The Spirit, this film essentially buried any future Frank Miller could have had in directing films (after gaining some notoriety for the first Sin City film).
- Fake American: The French Eva Green portrayed Ava Lord and New Zealander Marton Csokas played Damien Lord.
- Franchise Killer: Due to the poor box office numbers and mixed reception of the film, plans for the third film were cancelled.
- The Other Darrin: Several characters were recast due to either the untimely deaths or retirements of their previous actors.
- Dennis Haysbert replaces Michael Clarke Duncan, who passed in 2012, as Manute.
- Jamie Chung replaces Devon Aoki as Miho, due to Aoki being pregnant while filming was going on.
- Jeremy Piven replaces Michael Madsen as Bob.
- Josh Brolin replaces Clive Owen as Dwight McCarthy, as the story is set before "The Big Fat Kill" and Dwight's facial reconstruction. Owen was intended to return as Dwight post-surgery (with Brolin pre-surgery), but his schedule prevented it.
- Playing Against Type:
- Dennis Haysbert has built such a reputation playing Reasonable Authority Figures (police officers, military officers, the President of the United States, the spokesman for Allstate Insurance) that he's not entirely believable as a Scary Black Man.
- Alexa Vega makes a cameo as a stripper.
- Saved from Development Hell:
- The sequel had been in Development Hell for years, and was finally released in 2014, nine years after the first.
- In the back of Lost, Lonely and Lethal (published in December 1996), Frank Miller announced a story called "The Hard Good-Bye" that would feature Nancy teaming up with Marv to avenge Hartigan. The title ended up being used as a Retronym for the first arc while the story itself finally saw the light of day in A Dame to Kill For as "Nancy's Last Dance," 18 years later.
- Separated-at-Birth Casting: When Senator Rourke portrayed by Powers Boothe meets his illegitimate son Johnny even he notices the resemblance between the two of them and for all his faults he ain’t wrong! Boothe and Levitt are very believable as father and son.
- What Could Have Been:
- Angelina Jolie was Rodriguez's original choice for Ava Lord in the sequel, so much so that he was delaying production to correspond with her pregnancy. Amy Adams, Helena Bonham Carter, Anne Hathaway, Salma Hayek, Elizabeth Hurley, Scarlett Johansson, Jennifer Lawrence, Rose McGowan, Rachel Weisz and Michelle Williams were also considered.
- Jake T. Austin auditioned for the role of Johnny.
- Alexis Bledel was slated to return as Becky, but was unavailable.