Most comic book movies are light adventures aimed at kids. But some films in the popular genre, like Logan and The Dark Knight, have a darker tone.

Most of the comic book blockbusters that hit multiplexes are lighthearted adventures aimed at a young demographic. Although superheroes are just as popular among adults as they are among children these days, studios tend to make kid-friendly comic book movies, because these are usually $200 million tent-poles. The goal is to appeal to as many potential viewers as possible.

Still, there’s that rare occasion that a superhero movie with dark themes, graphic violence, an abundance of foul language, and even a little sexual content manages to slip through the cracks. So, here are The 10 Darkest Superhero Movies Ever Made, Ranked.

10 Kick-Ass (2010)

What would happen if a regular person decided to don a mask, go out on the streets, and dole out a Batman-esque brand of vigilante justice? That’s the question posed by Matthew Vaughn’s Kick-Ass, adapted from the Mark Millar comic book of the same name. It’s a question that’s been posed by many stories in the past, but it’s rarely tackled with such pitch-black humor.

Aaron Taylor-Johnson captures the role of a nerdy teenager in way over his head perfectly, while Nicolas Cage and Chloë Grace Moretz provide terrific support as a pair of masked vigilantes who are actually as competent as Batman.

9 Blade (1998)

Last summer, Marvel Studios announced that Mahershala Ali had been cast to play Blade in a new movie. As incredibly talented as Ali is ⁠— he’s a two-time Oscar winner who never fails to deliver the goods ⁠— he’s got some pretty big shoes to fill.

X-Men and Spider-Man are often credited with kicking off the long-standing trend of superhero blockbusters, but it was actually Wesley Snipes’ Blade movie, in which he played Marvel’s vampire hunter as a wisecracking badass. Blade wasn’t a particularly interesting character in the comics until Snipes came in to define his personality and earn him a legion of new fans.

8 The Dark Knight (2008)

Christopher Nolan’s The Dark Knight is the film that inspired a wave of dark superhero movies that didn’t come close to matching its cinematic brilliance. Parents were up in arms over the movie’s PG-13 rating when it was first released, and this was mainly thanks to the film’s iconic villain.

Heath Ledger’s portrayal of the Joker is truly disturbing, from impaling a man on a pencil to releasing a shaky homemade video of himself torturing a Batman wannabe to jamming a knife into a guy’s mouth and telling him his harrowing (if made-up) origin story. These make the movie an intense, almost terrifying experience.

7 The Crow (1994)

Based on James O’Barr’s seminal comic book, The Crow tells the story of a rock star who is brought back to life in order to avenge his own death, as well as the sexual assault and murder of his fiancée. Director Alex Proyas brought a bold, unique visual style to the movie, before his filmmaking craft went off the rails and he helmed the godawful Knowing and the even-worse Gods of Egypt.

The Crow marked the final film appearance of Brandon Lee before his tragic, untimely death, and the movie pays tribute to him in a truly heartfelt and meaningful way.

6 Logan (2017)

The first superhero movie to be nominated for an Academy Award for Best Adapted Screenplay, Logan takes the basic plot structure of the classic western Shane and transplants it into a comic book setting. Set in the near future, Logan picks up with an aging Wolverine whose adamantium skeleton is slowly weakening, and a Professor X on his deathbed who is sadly succumbing to dementia.

Wolvie reluctantly helps his cloned daughter ⁠— who he only just found out existed ⁠— to get across the country, and they leave a trail of blood and guts along the way. It was a fitting, if heartbreaking end to Hugh Jackman’s on-screen journey as Wolverine.

5 Darkman (1990)

After failing to secure the film rights to a couple of high-profile superheroes from the comic book world, including Batman, Sam Raimi decided to create his own superhero. Darkman stars Liam Neeson as a mild-mannered scientist who is disfigured by some hired goons and wears bandages on his face to cover it up. He’d been working on a synthetic skin for burn victims, which allows him to disguise himself as anyone.

As a horror director, Raimi wrote and directed Darkman less as a superhero movie and more as a classic Universal monster movie, making it much spookier and more violent than the average superhero flick.

4 Super (2010)

Before helming the Guardians of the Galaxy trilogy for Marvel, James Gunn created his own superhero, the Crimson Bolt, for an indie black comedy called Super. The Office’s Rainn Wilson plays Frank D’Arbo, an average workaday schmuck who decides to don a red suit and become a vigilante after his wife leaves him for a crime lord.

Super is one of the most ultraviolent superhero movies ever made, with the Crimson Bolt arming himself with a wrench and dropping it on criminals’ heads from great heights. Gunn shoots the violence with a gruesome bluntness, so it has even more impact.

3 Batman (1989)

Tim Burton was the perfect director to bring the Caped Crusader to the big screen. His glitzy, gothic vision of Gotham City in 1989’s Batman was influenced by German expressionist cinema, particularly Fritz Lang’s groundbreaking sci-fi opus Metropolis.

Michael Keaton’s casting as the Dark Knight was initially controversial, since he was known primarily as a comedy guy, but he proved to be the ideal Bruce Wayne. Scenes like Jack Nicholson’s Joker seeing the bleaching of his face for the first time in a dark basement and laughing hysterically wouldn’t feel out of place in a horror movie.

2 Dredd (2012)

After Sylvester Stallone sanitized the violence of 2000 AD comics with his PG-13 Judge Dredd movie, Dredd felt like a breath of fresh air. Forgoing the standard “gritty reboot” and jumping straight into outlandish, gut-wrenching, blood-soaked territory for a more faithful take on the source material, Dredd stars Karl Urban as the titular Judge, grimly dishing out his own brand of justice.

Urban is joined by Olivia Thirlby as Judge Anderson, the conflicted young rookie assigned to take down a drug ring with Dredd on her first day. Dredd plays like The Raid, but with more blood, more super slow-motion, and more Lena Headey.

1 Watchmen (2009)

While the recent HBO series has been praised as a worthier companion to the iconic Alan Moore maxiseries, there’s a lot to love in Zack Snyder’s movie adaptation of Watchmen. As with his other comic book movies, he ripped a number of frames straight from the pages of the source material, and used Warner Bros.’ unprecedented $130 million tentpole budget to really bring them to life.

Most importantly, he didn’t water down the graphic content from the comic book, including all the blood, swearing, and sexual violence for maximum shock value. Snyder’s director’s cut is a lot better than the theatrical version, so if you can get a hold of that, check it out.

NEXT: 10 Unmade Superhero Movies We Really Want To See

Next Lightyear: Keke Palmer's 10 Best Movies, According To Rotten Tomatoes