Josh Brolin as Dwight in Sin City: A Dame to Kill For. Credit: The Weinstein Company.

Sin City: A Dame to Kill For took a bullet over the weekend, earning just $6.5 million at U.S. cineplexes while Guardians of the Galaxy ($17.6 million for the no. 1 spot) and Teenage Mutant Ninja Turtles ($16.8 million and no. 2) continued to cash in, according to studio estimates compiled by Rentrak.

All three are comic book adaptations. Yet two are winning and one flopped. Why? And what, as investors, can we learn from it?

What audiences want from a comic book movie
Forget for a moment that Sin City: A Dame to Kill For is an R-rated movie defined by extreme violence amid a gritty, comic-book-like cinematography. The sequel to 2005's Sin City is still a comic book adaptation, and we in the audience have a feel for what that should be like.

Mostly, we expect a Marvel movie.

And when I say, "we," I mean everyday moviegoers. Any comic book fan who's been in the hobby for a few years knows that some of the best material exists outside the domain of Marvel and DC, among the ranks of lesser-known titles from small publishers. In 1993-94, writer-artist Frank Miller's Sin City series of anthologies were that kind of indie, published by Dark Horse Comics.

In 2005, the first adaptation of that material -- Sin City -- earned $158.8 million in worldwide grosses, an impressive haul for a film that cost an estimated $40 million to produce and another $37 million to market and distribute. Nine years and $6.9 billion in box office grosses later, Disney (NYSE:DIS) and Marvel have redefined what it means to make a comic book adaptation. Nearly every hit has been:

  • Timely.

  • Family friendly.

  • Supported by an existing fan base.

  • Part of something bigger.

Look at Guardians of the Galaxy, which taps into renewed enthusiasm for Star Wars (timely), embraces goofy humor at key times in the movie (family friendly), stars popular actors and is supported by a hot-selling comic book (fan base), and exists in the Marvel Cinematic Universe (is part of something bigger). No wonder this is the top summer movie at the U.S. box office.

Chris Pratt's performance as Star-Lord in Guardians of the Galaxy is closer to what we've come to expect from a modern comic book adaptation. Credit: Marvel Entertainment.

No forgiveness for this 'Sin'
By contrast, Sin City: A Dame to Kill For is an adult drama suffering mixed reviews for its degrading depictions of women characters. You can imagine how well this goes over in the wake of the #YesAllWomen movement on Twitter.

Female fans have also become more active in supporting genre entertainment. According to research from Eventbrite, women comprise 50% of under-30 fans who attend events such as San Diego Comic-Con. They're also spending more, which means catering to this segment of the fan population has never been more important. (Check out the "Future of Geek" panel at Comic Con, where industry colleagues and I discussed this in greater detail.)

"If you like gritty noir, problem drinking, car chases, awesome action, heavy bloodshed, and movies that look like comic books come to beautiful life, and you can handle some stereotypes and watching women get treated poorly -- this movie is for you. If not, forget it," writes Angela Watercutter over at Wired.

So far, most are forgetting it. With a B- CinemaScore -- think of it as a collective "meh" from audiences that saw it -- Sin City: A Dame to Kill For comes off as out of touch, and it's showing in the box office results.

Foolish takeaway
While some of the more profitable comic book adaptations trace their roots to indie comic book  properties -- 1994's The Mask, for example, or The Walking Dead on television -- at the cinema, the business has changed since 2008, when Iron Man set a stylistic tone that has become the norm for the genre.  

Every film to come after is measured by how well it executes the Marvel Studios formula. Unfair, you say? Of course it is. But that's the way the business is now, and why Sin City: A Dame to Kill For doesn't measure up.