The comic book world is full of heroes of every variety. Many had humble beginnings as mild mannered, uncomplicated crime fighters who only got involved in situations with clear cut distinctions between right and wrong. But not all characters see things so black and white. For some, heroic deeds fall on a tortuous greyscale gradient where blurred boundaries create fascinating plot lines and thought-provoking moral dilemmas. These vigilantes are the ones who are willing to compromise their moral integrity and sacrifice whatever is necessary for the greater good. And, since breaking the rules almost always brings trouble with it, they’re also some of the biggest badasses in the biz. These are the 10 greatest anti-heroes in comics.

10. Wolverine

Wolverine is the quintessential loner anti-hero. He’s always brooding about his checkered past and striking out on his own to find ways to atone. He is a character defined by conflict who is constantly struggling to control the raging demons within him while simultaneously serving the good of the world. Wolverine would just as soon kill a dangerous villain as he would send them to the justice system. His darkened past has him creeping in the shadows playing various roles as a spy, assassin, ravenous killer, honored warrior, and even teacher. But his persistent memory problems make it so he’s unable to remember what of his life was true. Which leaves you constantly guessing what his true motives are and what he’s capable of.

9. Marv

Creator Frank Miller describes him as “Conan in a trench coat”, and that’s about as accurate a description as you can get for Sin City’s Marv. This horribly scarred, monster of a man delights in causing horrible pain to anyone he feels deserves it, and he can take even more punishment than he dishes out.

Although he lives by his own code of ethics, he never lets moral restrictions stop him from doing what needs to be done, and nothing can stop him once he’s made up his mind. His only weakness might be his fierce loyalty to the people he cares about. In the end it’s love that gets him killed, but not before he stares death in the face, spits blood, and laughs.

8. John Constantine

John Constantine is a pretty mixed bag when it comes to professions. Magician, supernatural investigator, con man; he’s probably got all of them listed on his business card. But perhaps it’s this exact unconformity that has made him a staple of adult themed comics for almost three decades.

Far from one of those muscular, spandex-wearing  pretty-boys, Constantine’s drinking problem and smoking habit make him much more of a vagabond than someone you think would come rushing to your rescue. The appearance does suit his style though, since he often relies on his hardened street smarts as a means to maintain the upper hand and overcome adversaries. Of course, when push comes to shove, he’s got no problem using physical violence or demonic sorcery to get the point across. He’s even bested the lords of hell on several occasions so, even if he does look like a drug-addict in a trench coat, he’s certainly not one to be trifled with.

7. Spawn

All anti-heroes have some sort of tragic element to their story but Spawn probably takes the cake when it comes to lamentable origins. After being murdered by his friend Chapel, Al Simmons sells his soul to the ruler of hell so he can see his wife again. Unfortunately, the demonic lord alters the agreement a little and sends Simmons back to the Earth realm five years later as some sort of hell spawn creature with no memory of what he had done. After finally regaining his memories, he seeks out his wife only to find that she’s now happily married to his best friend, with whom she shares a child.

Fortunately for readers, tragic stories usually result in fascinating anti-heroes, and Spawn is no exception. He’s ugly, his methods are stylishly savage, and he obliterates the line between good and evil.

6. The Punisher

Frank Castle is a man who’s lost everything. As such, he doesn’t care too much about what happens to him or those who get in his way in his pursuit of vigilante justice. In fact, more often than not he’s wanted by police for his use of brutal tactics and extreme violence in dealing with criminals.

Unlike pretty much all other Marvel characters conceived around the same time, The Punisher seemed to express a kind of joy in killing people that could have been viewed as dangerous for a mainstream publication geared towards a younger audience. But his personality never seemed to soften. In fact, over the years The Punisher has become even more detached and delusional — believing himself at one point to be God’s personal tool for punishment on Earth. Nevertheless, the crazier Frank Castle gets, the more of a threat to the criminal element he becomes.

5. Judge Dredd

He may be “the law”, but Judge Dredd is still the worst nightmare for anyone looking to cause trouble in the post-apocalyptic metropolis known as Mega-City One. Armed with his trusty Lawgiver side-arm and fueled by a unyielding hatred of crime, Dredd is a threat to anyone who even considers committing the most minor of offences.

The idea of an exaggerated law system that deals only in absolutes is a terrifyingly pertinent one, that has kept the comic perpetually relevant. Dredd believes it’s his purpose in life to ensure that people who break the law are detained and sentenced immediately. And if the sentence happens to be death he’s more than willing to take on the role of executioner.

Although he does question his role in this fierce, dystopian regime from time to time, he’s ultimately a harsh product of harsh times created to bring justice. Which he does.

4. The Comedian

Eddie Blake is a gun-toting, cigar-chomping vigilante turned war hero with admittedly poor morals. Hell, as a sexual assailant with seemingly racist perspectives, he’s practically a criminal himself. But it’s precisely this sort of layered complexity that makes him so interesting — much like the appeal of fellow Watchmen character and anti-hero Rorschach.

The Comedian first became a crime fighter when he was 16 as a means of satisfying his sadistic love of violence. He never shows any genuine desire to right the wrongs present in society and emotional pleas have no effect on him whatsoever. This facet makes him all the more dangerous because, unlike characters such as Marv, there’s no human life he cares enough about to allow himself to be compromised.

3. Batman

Sure, he might have a moral code that prevents him from using lethal force, and his commitment to protecting Gotham City might seem pretty plain and simple, but Batman is a true-blooded anti-hero of the highest order. This is evidenced by the fact that the people he’s protecting are just as afraid of him as his foes, and he always has a contingency plan for battling any other superhero in the event that they become villainous.

Considering his mindset, this makes him one of the most powerful and dangerous people in comics. Bruce Wayne is a multi-millionaire who can have anything he wants and do anything he pleases, yet he chooses to put on a bat suit and go around fighting the criminally insane. The argument could be made that Bruce Wayne belongs in Arkham Asylum just as much as any of the whacked out villains he’s put there. He’s also the reason many of them re-offend, since they’re all hellbent on revenge against Batman once they get out, which makes him indirectly responsible for most of Gotham’s crime problems — an aspect he’s acutely aware of. So, while there’s no question that Batman performs heroic deeds, his motives for doing them might be decidedly less so.

2. Deadpool

There’s probably never been a more sadistic, fun-loving anti-hero than Deadpool. He’s got all the anti-hero trademarks: horribly disfigured, foul-mouthed, violence-loving, and moderate insanity. But, despite the fact that he makes a living killing people as a mercenary, Deadpool frequently finds himself fighting alongside Marvel’s goodie-goods like Spider-Man and the X-Men, although not always by choice.

When Deadpool first appeared, he was hired by a super-villain to fight the time travelling mutant known as Cable. There really wasn’t any moral ambiguity at all to his character back then. He was simply the new villain in town. It was only years later that Deadpool began to become the anti-hero we know and love today. In essence, this evolution makes Deadpool a much more interesting character, both within Marvel canon, and from the readers perspective.

1. Rorschach

Unlike The Comedian, who seems to express indifferent moral views, Rorschach has an incredibly strict moral code that he lives and dies by. Even when government regulations required all costumed heroes to reveal their secret identity, he didn’t give in, choosing instead to live as a wanted man and kill anyone who tried to stop him from dispensing his own special brand of brutal justice throughout the city.

It’s almost as if Rorschach is a “Frankensteined” anti-hero, stitched together from the best parts of other great anti-heroes. He’s got the justice sense of Batman, the fearlessness of Daredevil, the killer intent of The Punisher, and the charisma of Deadpool. He’s like a mysterious, uncompromising force for the innocent lives he aims to protect.

If a true anti-hero is measured by their willingness to do whatever it takes to uphold truth and integrity, no matter the personal cost, than Rorschach is surely the ultimate embodiment as he willingly chooses death over complacent public deceit.