In the past decade or so, big-screen adaptations of comic books have risen from the occasional blockbuster to one of the most prominent and financially successful types of films out there. The introduction of the Marvel Cinematic Universe and the ensuring race for other studios to develop similar shared universe projects has led many to wonder if the market was nearing over-saturation, but the record-breaking success of the hard-R Deadpool may reinvigorate the industry and its largely family-friendly approach to comic book properties. But as James Gunn recently pointed out, studios and filmmakers would be wise not to simply cut-and-paste that film’s style and tone to other comic book properties.

Still, Deadpool is far from the first R-rated comic book movie to honor the source material and deliver a satisfying film experience in the process. So, as the Merc with the Mouth proudly sits atop the box office, we look back at some of the best comic book films to ever earn an R rating. For the record, we’re focusing largely on mainstream live-action adaptations and basing our ranking on a combination of box office receipts, response from fans, and the impact each film has had on the industry. Cue the music.

15. Road to Perdition (2002)

Best Comic Book Movies Road to Perdition 15 R Rated Comic Book Movies That Worked

A Depression-era mobster film isn’t the first thing that springs to mind when one pictures a comic book film, but director Sam Mendes (Spectre) beautifully brought Max Allan Collins’ graphic novel to life with this sleek, gorgeously shot film. Tom Hanks stars as a mob enforcer who is accompanied by his surviving son on a quest for revenge against the man who murdered their family.

Although its comic book roots may not be readily apparent, Road to Perdition features the contemplative spirit, detailed shot composition and strong characters that have come to define the best of the medium. Moreover, its status as a major awards contender that year helped broaden the mainstream perception of what comic book films could be, an understanding that has only continued to build in the years since its release.

14. Ichi the Killer (2001)

Ichi the Killer 15 R Rated Comic Book Movies That Worked

From 1998 to 2001, Hideo Yamamoto chronicled the tale of psycho-killer Ichi and his battles with the yakuza gangs. Takashi Miike’s subsequent 2001 adaptation, Ichi the Killer, received even more attention for its extreme violence and torture than the manga that inspired it. The film was subsequently banned in several countries following reports of vomiting and fainting at screenings of the film on the festival circuit.

Coming from the director of Audition, it shouldn’t come as any surprise that the film includes some of the most controversial depictions of violence in cinema history. Still, its vision and precise tone is so well-executed that it’s hard to deny that Miike brings a great deal of artistry to his interpretation of the source material, even if his film isn’t for everyone. Ultra-violence and dark humor don’t get much crazier than this.

13. Watchmen (2009)

Watchmen 15 R Rated Comic Book Movies That Worked

Aside from the controversy surrounding its altered ending, Zack Snyder’s Watchmen remains so reverent to Alan Moore and Dave Gibbons’ masterpiece that it’s curious why the film has become one of the more divisive comic book adaptations in recent memory, especially since one of the most common criticisms fans have with such releases centers on departures from the source material.

Nevertheless, Watchmen remains the most underrated and ambitious of Snyder’s plethora of comic book-related endeavors. For years, the project was deemed unfilmable, and though it didn’t exactly light up the box office, the film has developed a cult following, thanks in large part to fan-favorite performances by the likes of Jackie Earle Haley and Jeffrey Dean Morgan. For Snyder’s effort, Warner Bros. ultimately handed him the keys to the DC Cinematic Universe.

12. A History of Violence (2005)

Best Comic Book Movies A History of Violence 15 R Rated Comic Book Movies That Worked

There are no capes or cowls in A History of Violence, but David Cronenberg’s 2005 thriller — which centers on a small-town family man who becomes a local hero after stopping an attempted robbery — does serve as a subversive commentary on humanity’s capacity for violence and the implications that such acts bring about. In doing so, the film translates the John Wagner/Vince Locke graphic novel into a celebrated exercise in neo-noir.

Anchored by a powerful performance from leading man Viggo Mortensen, A History of Violence continued Hollywood’s trend of developing unlikely comic book titles into hit films. Cronenberg’s take was met with universal critical acclaim and Oscar nominations for supporting actor William Hurt (in a famously brief appearance) and Josh Olson’s screenplay. Moreover, it led to a second Cronenberg/Mortensen collaboration: the equally praised 2007 gangster film, Eastern Promises.

11. Wanted (2008)

Angelina Jolie in Wanted1 15 R Rated Comic Book Movies That Worked

Nowadays, the work of comic book writer Mark Millar is routinely considered material ripe for a big-screen adaptation (more on that a bit later). Wanted — based on the series by Millar and artist J.G. Jones — was the first release to translate his stories into hit films, and director Timur Bekmambetov (Abraham Lincoln: Vampire Hunter) elevated the tale of Wesley (James McAvoy), Fox (Angelina Jolie) and the Fraternity with a distinctive visual take.

Bolstered by Jolie’s star power, the film was a box office smash in the summer of 2008, earning $341 million at the worldwide box office. It also launched McAvoy to new levels of stardom, setting the stage for his role as the young Professor X in X-Men: First Class just three years later. Despite Wanted‘s widespread success, there’s still no telling when (or if) we’ll get the long-in-development sequel it so richly deserves.

10. Oldboy (2003)

oldboy 10 underrated films available stream netflix 15 R Rated Comic Book Movies That Worked

Forget the 2013 Hollywood remake. The original South Korean adaptation of Oldboy still stands as the defining take on the manga by Nobuaki Minegishi and Garon Tsuchiya. Starring Choi Min-sik as a businessman who is mysteriously imprisoned for 15 years, the film presents a dark, disturbing tale of vengeance that has made a lasting impression on audiences.

With a fresh take on the revenge thriller and a story full of memorable twists, Park Chan-wook’s film remains one of the most unforgettable pillars of the genre to date. Upon its release, Oldboy won the Grand Prix at the Cannes Film Festival and has since been widely considered one of the best examples of Asian cinema by moviegoers the world over. No small achievement for such a wonderfully strange film.

9. Dredd (2012)

Movies That Deserve A Sequel Dredd 15 R Rated Comic Book Movies That Worked

Fans of the John Wagner/Carlos Ezquerra character that made his first appearance in sci-fi anthology series 2000 A.D. were roundly disappointed when Judge Dredd made his first big-screen appearance in a 1995 Sylvester Stallone vehicle. 17 years later, Dredd managed to redeem the character with a thrill ride that wisely keeps the character’s backstory and his face a mystery, relying instead on his stone-faced, relentless pursuit of justice.

The film was met with enthusiasm by devoted comic book movie fans and lovers of high-octane action cinema, but despite the fervent response from some, Dredd was a box office flop, bringing in just $35 million worldwide. That hasn’t stopped fans (and star Karl Urban) from continuing to rally support for a sequel, though at this point there’s been no indication that it’ll arrive anytime soon. At least fans of the Judge have one solid film to enjoy for now.

8. V for Vendetta (2006)

Hugo Weaving in V for Vendetta 15 R Rated Comic Book Movies That Worked

Following his disappointment in the film adaptations of From Hell and The League of Extraordinary Gentlemen, legendary comic book writer Alan Moore swore off receiving credit or royalties for any subsequent films based on his work. That’s a shame in many respects, because V for Vendetta — based on the graphic novel by Moore and David Lloyd — has become one of the very best examples of R-rated comic book cinema, despite the changes it made.

The film follows Hugo Weaving’s masked revolutionary V as he mounts an attack on the tyrannical government of a U.K.-based dystopian future. In addition to its rich political and social allegories, V for Vendetta features stellar performances (most notably by co-star Natalie Portman as a young woman who joins V’s cause) and action set pieces influenced by the Wachowskis, who wrote the screenplay and produced the film. Moviegoers may never see the fifth of November the same way again.

7. Kingsman: The Secret Service (2015)

Colin Firth Kingsman 2 15 R Rated Comic Book Movies That Worked

The mind of Mark Millar strikes again with this playful send-up of espionage thrillers inspired by the comic book series from Millar and artist Dave Gibbons. Like the quirky bastard child of Millar’s Wanted and Kick-Ass, Kingsman: The Secret Service centers on a secret society of super-spies, but tackles the material with a self-aware sense of humor that subverts genre conventions and delivers a supremely fresh and modern take on the spy genre.

Ostensibly led by Colin Firth (in an against-type role as a gentlemanly badass), the film was the breakout role for young up-and-comer Taron Egerton, who will lead both a Kingsman sequel and a new Robin Hood: Origins film. The 26 year old Egerton may even be in line to be the next Han Solo. Even more impressively, Kingsman: The Secret Service stands as the biggest moneymaker to date for both Millar and director Matthew Vaughn (X-Men: First Class). Just like that, a new franchise was born.

6. 300 (2007)

Gerard Butler in 300 15 R Rated Comic Book Movies That Worked

Few figures are as iconic in the comic book world as Frank Miller. Yet it wasn’t until the mid-2000s that Hollywood finally started to develop films based on his work. To date, 300 represents the apex of Miller’s success on the big screen, likely due to its mainstream appeal as a swords-and-sandals epic. Like Sin City before it, the film — based on Miller’s series with Lynn Varley — painstakingly replicates the comic book’s visuals to great stylistic effect.

As the fearsome King Leonidas, Gerard Butler spouts off one memorable line of dialogue after another (“This. Is. Sparta!”) in a role that has become so iconic that the actor looks to be channeling his own performance in the upcoming release Gods of Egypt. Sure, 300 may be one of the best examples of style-over-substance filmmaking in recent memory, but that doesn’t negate the achievements of director Zack Snyder (in his first comic book film) and his team.

5. Kick-Ass (2010)

Aaron Taylor Johnson in Kick Ass 15 R Rated Comic Book Movies That Worked

Kick-Ass hit theaters in 2010, just as the superhero boom was really gaining steam. The Marvel Cinematic Universe was still in the midst of Phase One, and DC Comics hadn’t even unleashed Green Lantern onto the world. The film’s pseudo-parody of the genre came at just the right time to capitalize on its exploding popularity, and director Matthew Vaughn deftly balanced a more realistic take on costumed heroes with poking fun at the absurdity of it all.

Aaron Taylor-Johnson and Chloë Grace Moretz represent the film’s dual approach to superheroes, with the former as the inept would-be hero and the latter as a foul-mouthed assassin the likes of which mainstream moviegoers hadn’t seen up to that point. The result was an unexpected blockbuster based on Mark Millar and John Romita Jr.’s series that transformed its young leads into major stars and had Hollywood salivating for another Millar adaptation. Too bad the 2013 sequel was only half as fun.

4. Sin City (2005)

Bruce Willis in Sin City 15 R Rated Comic Book Movies That Worked

Co-directed by Frank Miller and Robert Rodriguez, Sin City started a trend of comic book adaptations that were unyieldingly faithful to the source material. But thanks to its big-name ensemble cast, the film transformed Miller’s pulp noir series into a surprising box office smash. Even with its extreme violence and unproven mainstream appeal, the ground-breaking, green screen-heavy aesthetic and take-no-prisoners storytelling was a major hit with critics and audiences alike.

While some comic book adaptations can be more easily disassociated from their published counterparts, Sin City feels every bit like the comics brought to life. A critical step in the continuing evolution of the medium, its release ushered Miller and his work into the Hollywood spotlight in a way he hadn’t previously been. Moreover, the film prepared moviegoers for radical new approaches to comic book films centering on unconventional anti-heroes.

3. The Crow (1994)

Revenge   The Crow 15 R Rated Comic Book Movies That Worked

After such a long gestation period, it remains to be seen when (if?) the on-again/off-again remake of The Crow will ever get off the ground. Fans may be hesitant about a potential re-telling of James O’Barr’s story about a musician who returns from the dead to avenge his murder and that of his true love, but the film has tons of potential to connect with modern audiences, given how ahead of its time the original was.

Under the standout direction of Alex Proyas (Dark City), The Crow spawned a rabid cult following and several sequels with a morally complex tale of vigilante justice that captured the imagination of moviegoers. The film’s legacy may be defined in part by the tragic accidental death of star Brandon Lee during its production, but its ominous tone and emotional complexity fit right in with more recent “dark and gritty” comic book films like The Dark Knight.

2. Blade (1998)

Wesley Snipes in Blade 15 R Rated Comic Book Movies That Worked

The early 2000s will forever be remembered as the era in which Marvel heroes like Spider-Man and the X-Men finally made their long-awaited leap to the big screen. However, Blade beat both franchises to the punch with a bloody opening sequence that brilliantly set the tone for Wesley Snipes’ take on the human/vampire hybrid — created by Marv Wolfman and Gene Colan — who doggedly hunts the undead.

Kicking off the first superhero franchise led by an African-American superhero, Blade remains one of the most underrated milestones of comic book cinema, as well as one of the most notable examples of how an R-rated adaptation can thrive. Though the series fell apart by the third entry, it’s only a matter of time before the Daywalker makes his triumphant return to the big (or small) screen now that Marvel Studios has the rights back.

1. Deadpool (2016)

deadpool movie images new mutants 15 R Rated Comic Book Movies That Worked

No one should be surprised to see that The Merc with the Mouth tops our list of R-rated comic book films. Since hitting theaters, Deadpool has been handily breaking one box office record after another, soaring far above expectations to deliver a film that represents the ultimate culmination of what has worked in its predecessors. Exceedingly violent and shamelessly profane, the film stays true to Rob Liefeld and Fabian Nicieza’s fan-favorite character and, following years of development hell, single-handedly redeems his disappointing appearance in X-Men Origins: Wolverine. Moreover, the film does all this with a brazen self-aware wit that doesn’t undermine its position as a pivotal new chapter in Fox’s ongoing X-Men franchise.

Perhaps it’s the pitch-perfect casting of Ryan Reynolds or the film’s brilliant marketing campaign that is responsible for the overwhelmingly positive response from both critics and audiences. Whatever the case may be, Deadpool has managed to become a runaway success, and, as a result, it already appears to be steering the future of the industry. Tim Miller (in his directorial debut!) delivers the film at a time when the potential for audience fatigue appeared to have been reaching a crossroads, as 2016 brings with it more than half a dozen major big-screen comic book adaptations. Totally befitting its outrageous title character, Deadpool has broken all the rules in its attempt to crumble conventional wisdom regarding how to make comic book films. Here’s hoping the future stays this bright.

Going forward, there’s no telling which superheroes will get the chance to headline their own R-rated films, but the films listed above have certainly paved the way for a broader variety of projects to hit the big screen. What’s your favorite R-rated comic book film? Share your thoughts in the comments section below.

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