When it comes to superhero villains, it doesn’t get any better than the Batman rogues gallery. Representing the diabolical best of the dim, gritty and disturbed playground of Gotham City, these delinquents stand in perfect opposition to the crime fighting Caped Crusader. Where as the world of Superman is exemplified by shining heroics (for the most part), Batman’s is defined by the evildoers that terrorize it from within its deepest shadows. What makes them standout is that they are all just a few shades of grey away from the Dark Knight himself. That, and they enjoy dancing with the devil in the pale moonlight.

We’ve already taken a look at some of Batman’s worst villains of all time, so why not now take a walk through some of the best to have graced the wretched halls of Arkham Asylum.

Here are the 15 Greatest Batman Villains Of All Time.

15. Killer Croc

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When written right, Killer Croc is as good as Gotham villains come. As of late, the character has been reduced to a large mutated reptile with little ambition beyond eating Batman. However, in 1983’s Detective Comics #523, Killer Croc started off as a far more interesting villain, so much so that some believe his backstory was the true inspiration for Tim Burton’s Penguin in Batman Returns.

When Waylon Jones was born with a rare scaly skin condition and relentlessly abused as a result, it was only natural he become a murdering psychopathic cannibal. After a quick stint finding acceptance with a traveling circus, he ended up in Gotham City. Where as in some versions you might find an anthropomorphic reptilian lackey, Killer Croc was always meant to be a deformed man who cunningly controls Gotham’s underworld from its deepest sewers. And eats people. Or, if you’re Harley Quinn, be a big teddy bear.

The physically menacing Croc is a fantastic match for the Bat, combining criminal aspiration with monstrous impulses. By letting his condition dictate his life (e.g. sharpening his teeth, crocodile style blitz attacks and the like) this former freak show wrestler has transformed himself into one truly scary rogue. Fortunately, this is the version that appeared in Suicide Squad, right down to his cannibalistic tendencies.

14. Black Mask

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Batman has his share of fantastical villains, but he also has some terrifyingly lifelike ones like the vicious mob boss, Black Mask. Basically an earlier, cooler version of the uber popular Hush, this crime lord has a long history with Batman, having actually grown up with Bruce Wayne. Born Roman Sionis, he was the by-product of self-absorbed wealthy parents who cared more about their social standing than his well-being, using outward appearances to impress the likes of the Waynes despite privately despising them. Because of his parents’ deceptions, he grew obsessed with the idea of masks. After killing them both, he not only inherited the family fortune but, after losing their company to Wayne Enterprises, took the opportunity to forge a new identity by carving a black mask out of his father’s casket and becoming a leader of Gotham’s crime world.

In recent years, the character has become a little less grounded in reality (he’s gained the ability to control minds using his mask). Despite this, the Black Mask remains a twisted adversary with a talent for striking his enemies where it hurts most, namely by ruthlessly torturing their friends and family. To that point, he is a member of the elite club who’s resumé sports a dead Robin (in this case, the character’s fourth incarnation, Stephanie Brown). While many of Batman’s villains resort to over-the-top dramatics and wacky gimmicks to fuel their crimes, the Black Mask retains a creepy dignity rooted in good old fashioned sadism and the use of a well fired gun.

13. Clayface

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Any superhero who’s worth his cape has got at least one shape-shifting villain. For Batman it’s Clayface, a hulking mud monster with the ability to reshape his body, turn his limbs into a menagerie of weapons, look like anyone he choses, and render nearly all forms of physical attack useless by melting.

Though his backstory is as shifty as he is, Clayface has provided Batman with a compelling enemy since the ’40s. He made his debut as B-list horror actor Basil Karlo, who goes on a killing spree wearing the monster mask of a film he starred in called “Clayface.” The villain would be rebooted as treasure hunter Matt Hagen, who gains the ability to shapeshift after coming into contact with radioactive protoplasm. Later, scientist Preston Payne steals a sample of Hagen’s blood to cure a deformity only to turn into a clay monster who loses his mind. Perhaps the best and most tragic version of the character comes from the ’90s Batman: The Animated Series, which fused his past comic counterparts and ended up becoming the visual template for future appearances.

An incredibly difficult adversary to detect and destroy, with an emotional backstory and just the right amount of science fiction, Clayface is a vastly underutilized character that would be a perfect villain for Ben Affleck in his upcoming solo Batman flick – assuming the film universe doesn’t follow in the footsteps of recent comics.

12. Poison Ivy

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For anyone who’s ever been punished by 1997’s Batman & Robin, you may have forgotten that the seductive eco-terrorist, Poison Ivy, is one of the Dark Knight’s most iconic villains. With her ability to pretty much do whatever she wants with plants (and we mean anything), this Gotham City siren is a lethal foe, made all the more dangerous by the way she can entice any man to do her bidding, even Superman.

She first appeared in 1961’s Batman #181 as the botanical biochemist Pamela Isley. After being forced to consume (or was injected with, depending on the origin story) a poisonous plant, she grows into the ravenous Poison Ivy, obsessed with protecting the planet’s plant life. While this may seem like a noble cause (we love sneezewort as much as the next guy), when you take into account she plans to do so by eliminating all human life, you can understand why Batman might want to intervene.

A perennial cosplay hit and fan-favorite (despite Uma Thurman’s best efforts), Poison Ivy has spawned some of the most enjoyable storylines in recent memory – like the time she gave Supergirl her first kiss or when she teamed up with her more-than-platonic partner in crime, Harley Quinn, whose meta-human abilities came from Ivy. A one-time member of the Suicide Squad, here’s hoping Poison Ivy finds her way into the sequel or, fingers crossed, Harley’s upcoming solo outing.

11. Penguin

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Batman villain campiness at its best, the Penguin has been a long-time mainstay in the Caped Crusader’s rogues gallery. Having debuted in 1941’s Detective Comics #58, Oswald Chesterfield Cobblepot III originally got his start as your run-of-the-mill crook stealing precious bird related items, perhaps best embodied by Rocky’s own Burgess Meredith in the ’60s Batman TV series. Later, following Crisis on Infinite Earths, the Penguin came back with renewed vigor and complexity as one of Gotham City’s most notorious crime bosses.

Despite being the grotesque face of the city’s criminal underworld, Penguin has also shown a practical, sometimes even quasi-legitimate business side, committing his treacherous acts less out of a need to wreak havoc and more out of a pursuit for personal and financial gain. This so-called Gentleman of Crime has at times been known to show some compassion, and has even worked cooperatively alongside Batman. Of course, usually it’s all a front, and behind closed doors, he is every bit the ruthless monster his outward appearances convey. Adding to his dangerousness, the Man of a Thousand Umbrellas has displayed a refined intelligence and sophistication, not too mention far more sanity, than most of this villainous flock (yeah, we went there).

10. Talia al Ghul

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It’s possible that no other character on this list has a closer personal relationship with Batman than Talia al Ghul. The daughter of Ra’s al Ghul, she was trained by her father to help run his League of Assassins and be the heir to his throne. Even more noteworthy, she is the mother of Batman’s son, Damian Wayne, who she later played a role in killing.

Batman doesn’t make a habit of knocking up his enemies, so right off the bat you know she’s something else (though to her evil credit, she probably drugged him into having coitus). Aside from that, she has repeatedly expressed a desire to be with her “beloved” despite Batman consistently turning her down, which places her in one of the most lethal of all roles: love scorned woman in command of a bunch of ninjas. While she has been known to help Batman from time to time, it’s hard to find too much good in Talia, since most of what she does is in her own self-interest to destroy humanity, motivated by the controlling influence of her father. Take Marion Cottillard’s portrayal of the character in Dark Knight Risesfor example.

Once writer Grant Morrison got his hands on the character, particularly in Batman, Inc., Talia loses all hope of redemption. Namely because she genetically creates an enhanced clone of her son that she has assassinate her actual son by beating the crap out of him (who’s 10-years-old, by the way) and then kill by impaling him with a massive sword. Overall, she and Batman turn out to be pretty crappy parents, but Talia al Ghul takes it to Cersei levels of horribleness (minus the incest).

9. Mr. Freeze

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Mr. Freeze is not your typical Batman villain. He could care less about riches, power or chaos, and, despite all outward appearances, he isn’t a cold-blooded killer at heart. All he cares about is saving his sick wife, Nora. After the gifted scientist Victor Fries marries the love-of-his-life only for her to contract a rare terminal illness, he’s forced to work for a corrupt company in hopes of finding a cure. Unable to do so, he steals equipment to preserve her in a cryo-stasis. When the company’s evil boss finds out, he tries to kill Fries, which results in an accident where the scientist can only survive in sub-zero temperatures. Fashioning a domed refrigeration suit to keep his body sufficiently frozen (along with a laser-powered ice gun), Mr. Freeze was born.

Disregarding his notorious, and all around horrible portrayal by Arnold Schwarzenegger in Batman & Robin, the character has one of the most touching storylines and coolest (Boom!) voices of all Batman’s foes, thanks in particular to his appearance in Batman: The Animated Series. Sure, he breaks the law and coldly kills a crap load of people, but he does it all in the name of love, not malice. Even Batman can sympathize with that. That’s why it’s hard not to feel bad for the guy every time he gets defeated by a thermos of chicken soup.

8. Scarecrow

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Like so many of the villains on this list, Scarecrow has been with Batman from the beginning of the Golden Age, first appearing in World’s Finest Comics in 1941. The result of an abusive upbringing that left him forever traumatized, an unhinged Dr. Jonathan Crane still somehow managed to become a professor of psychology and a clinical psychologist. However, after firing a gun in class, he’s dismissed, driving him to become the Master of Fear.

Equipped with a terror-inducing gas that forces victims to face their worst fears, the Scarecrow preys on the citizens of Gotham with a commandeering creepiness. Of all Gothamites, Bruce Wayne, who formed his superhero persona out of a childhood fear of bats, presents a compelling target for Dr. Crane’s psychological warfare, not to mention sharpened scythe. Though fear may be Batman’s greatest crime fighting tool in striking terror in the hearts of criminals, he has met his match in Scarecrow’s abilities to release its dreadful powers.

7. Hugo Strange

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No other villain on this list is as obsessed with the Dark Knight as Professor Hugo Strange (save for maybe one). And few have bested him as often as this genius psychiatrist, particularly in ruling his personal life. Still, Strange hasn’t garnered much popularity in the mainstream, though that all may change after his recent appearance in Season 2 of Gotham and rumored role in Suicide Squad.

One of Batman’s earliest adversaries (predating anyone else here, interestingly enough), Hugo Strange made his debut in 1940’s Detective Comics #36. As far as backstories go, Strange’s is a mystery. He pretty much just appeared on the scene and started creating problems from day one. Since then, the deranged doctor has played a prominent role in two of Batman’s coolest comic books, Batman and the Monster Men and the anthology Strange Apparitions. Then there’s the disturbing Batman: Prey and very odd Batman #356, in which Strange monologues at length about how much he loves admires Batman to his girlfriend (who happens to be a mannequin) and becomes so convinced he’s the real Caped Crusader that he dresses up as him.

Sure he’s bats*** crazy, but he’s also incredibly smart, being one of the few to surmise Batman’s secret identity. If that’s not enough, Batman himself has called this Amish bearded villain “the most dangerous man in the world.” Coming from a guy who was once called the same by Superman, that’s something.

6. Bane

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He broke the Bat. What else is there to say?

The pinnacle of physical and mental criminality, he is literally the Bane of Batman’s existence. The by-product of a hard knock life spent growing up in a corrupt prison, he spends his youth killing people using a knife concealed in a teddy bear named Osito. In the comics, he is terrorized by dreams of a monstrous winged creature, spawning a personal fear of bats. Later, after nearly dying from an experimental super soldier program that hooks him on Venom and lets him escape his confinements, Bane sets his sights on Gotham. Not unlike his prison, Bane believes the city is ruled by its fear of Batman, who he sees as the personification of the demon that haunted his childhood dreams. By masterfully pitting the deranged inmates of Arkham (many of which we find here) against Batman, he ran the Dark Knight through a gauntlet of evil while establishing himself as the ruler of Gotham’s gangland. Oh yeah, and he broke Batman’s back over his knee, mercilessly leaving the Caped Crusader a paraplegic.

Bane has yet to eclipse his complete and utter domination in Knightfall, accomplishing little since. Then again, how do you follow up a performance like that? (Unless you’re Tom Hardy.) Since then, he has notably teamed up with other supervillains such as the Secret Six and even briefly the Suicide Squad. Regardless of how much facetime we get though, Bane remains the architect of Batman’s greatest defeat. A bulking mass roided out on Venom pumped directly into his brain, he is one of the most physically imposing figures Gotham City has ever seen. (Just ask Killer Croc.) Perhaps even more impressive is that Bane is one of Batman’s most intelligent foes. Case in point, he deduces Batman’s secret identity from merely watching the way Bruce Wayne moves. Safe to say, no one has power over him.

5. The Riddler

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Batman is a pretty clever guy, but when put up against the brain teasing Edward Nigma, his usual intellectual superiority meets its match. First appearing in 1948’s Detective Comics #140, the Riddler has owned a varying backstory and seen different manifestations, at one point even going legit as a PI. Originally, the Crowned Prince of Conundrums was just a curious young boy, who after successfully cheating to win a puzzle contest, developed a fascination with riddles. When he was older, the working class Nigma (originally Edward Nashton) turned to a life of crime to entertain himself, but found his exploits only gained attention after they were elaborately tricked out, and so devised the ostentatious persona of the Riddler.

The Riddler seems to be in a class of villain all his own. He’s not exactly scary or brutal (at least most of the time), but rather a playful addition to the otherwise dark, gritty world of Batman. (Those colorful leotards don’t hurt either.) At his best, this enigmatic evildoer is a riddling madman hellbent on pitting his wits against the world’s greatest detective. But don’t take his penchant for puzzles and incessant honesty as a sign of weakness. His manipulations throughout Hush and his disastrous reign in Batman: Zero Year (one of the best moments from the New 52) are proof positive that the Riddler can be terrifyingly deadly. Either way, seeing the Caped Crusader try to solve one the Nigma’s over-the-top convoluted plots is always a pleasure, or should we say, joygasm.

4. Harley Quinn

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Is it just us or does Batman have the best selection of female characters in all of comics? Rounding out the Gotham City Sirens (a villainess trio that includes Poison Ivy and Catwoman), is the bubbly, psychotic killer, Harley Quinn. It’s quite a testament that a sidekick who got her start on a kids animated TV show and was inspired by a soap opera dream sequence has quickly become one of the Batman’s most popular associates. Originally intended as a one-off for the Batman animated series episode “Joker’s Favor,” the character was such an overnight hit that she was brought back several more times. From there she broke into comics, quickly becoming a best-seller. A solo series followed, along with a spin-off comic with the aforementioned Sirens. To top off her mallet wielding success, we’ll get Margot Robbie’s vicious, and what looks to be scene stealing, interpretation in Suicide Squad.

What’s not to love about this Brooklyn-accented, gleefully amoral and mentally unbalanced villainous vixen? She was an Arkham psychiatrist who, after falling hopelessly in love with Mistah J, is willingly led into a life of passionate crime. Even more endearing is her unhealthy commitment to her puddin’, helping garner sympathy for an otherwise unsympathetic character. Just take a look at her confession in Injustice and tell us otherwise.

With Suicide Squad, Harley is set to violently explode onto the mainstream, shedding her comical jester outfit and taking on a whole lot more than just a man in a bat suit. But that should come as little surprise – she’s a bad guy, it’s what she does.

3. Two-Face

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The former White Knight of Gotham, Two-Face is perhaps the most tragic character on the list. Thanks to Christopher Nolan’s The Dark Knight, most are familiar with his story. At one time the city’s righteous crime fighting District Attorney, he gets horrifically disfigured after a vindictive mob boss throws acid on his face (unless you’re watching the aforementioned movie, in which case, the Joker did it). Despite first appearing in 1941, Two-Face was missing throughout the entirety of the Silver Age with little mention of him for over 16 years, except for that time he was almost played by Clint Eastwood on the ’60s TV show.

Eventually, Two-Face returned, taking his deadly obsession with duality to new extremes. Due to the unpredictability of his coin, neither fans nor Batman can ever be certain how the villain will act. What’s more, he is (or at least was) one of the few friends and confidants Bruce Wayne ever had, adding a personal touch to their encounters. Overall, few have embodied the dichotomy of good and evil like Harvey Dent, save for perhaps the Knight of Vengeance himself. Representing both the best and worst of Gotham, Two-Face and Batman are two sides of the same coin.

2. Ra’s al Ghul

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While most of Batman’s villains limit their criminal scope to Gotham City, Ra’s al Ghul operates on a whole other level. Our very first impression of this regal killer comes in 1971’s Batman #232, when he walks right in and immediately reveals that he knows who Bruce Wayne’s alter ego is. A super intelligent, mystical international assassin, the Demon’s Head adds some much needed gravitas to the rogues gallery.

Given he was born over 700 years ago, Ra’s al Ghul’s backstory is long and intricate. He starts off as part of a nomadic Arabian tribe, discovers the youth rejuvenating Lazarus Pit while trying to save a sadistic prince who eventually kills the love of his life, learns to fence shirtless, creates an organization with the goal of eliminating the world’s evils by destroying all of humanity (in order to then rebuild it), and has a daughter named Talia with a hippie he meets at Woodstock (yep, that Woodstock).

Despite being one of Batman’s deadliest foes, Ra’s is a difficult villain to hate. After all, he has an admirable predilection for wanting to restore balance to the world, even if his means may be a bit questionable – like the time he tried to grow a race of super-humans inside some sperm whales. On top of that, he’s just as much a fan of Batman as we are, so much so he is constantly trying to convince the Caped Crusader to succeed him as the leader of the League of Assassins and hook up with his daughter. Also, he looks like Liam Neeson.

1. Joker

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Was there ever any doubt who would be in the top spot? As much as anyone might like to try, there’s no denying the Joker is the ultimate agent of chaos, a different class of criminal and Batman’s number one arch-nemesis. Obscenely dangerous, wildly unpredictable and always one step ahead of our masked vigilante hero, the Joker is guaranteed to go up against the Dark Knight in the most horrific of ways and provide Gotham City with a much needed, ill-humored enema.

Fittingly, the Joker appeared in 1940’s Batman #1, though his origins are shrouded in mystery and constantly changing. Since then he has featured in some of the most important comic books of all time, including Alan Moore’s The Killing Joke, Frank Miller’s The Dark Knight Returns and A Death in the Family, where he tops yet another list as the purveyor of the most brutal death of Robin. A pop culture icon right up there alongside the Bat and Supes, he has appeared in everything from art pieces to roller coaster rides and, of course, movies. Most recently, we’ve seen the Harlequin of Hate doing what he does best in the animated version of The Killing Joke (voiced by Mark Hamill) and as Jared Leto’s turn in Suicide Squad.

In the end, how do you fight a villain who doesn’t care about money, power, fame, respect, or even his own life? As far as totally insane purple suited grinning madmen go, the Joker can do it all and proves that even the most righteous of superheroes can have one very bad day, particularly if it means breaking his own neck or having his heart ripped out by Superman. Not only the greatest of Batman’s enemies, the Joker is arguably the greatest villain, and one of the greatest fictional characters, of all time. In any medium. Ever.

Honorable Mention: Catwoman

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One of Batman’s most common foes and one of comics most famous female characters, Catwoman is everything from a thief to an ally, mob boss, anti-hero and prominent (sometimes explicit) Dark Knight love interest. Astonishingly acrobatic, morally ambiguous and armed with an endless supply of cat puns, this patent leathered feline burglar is deserving of a place on any best of list. However, her predilection for heroics keeps her from earning a hard spot.

Easily the softest villain here, Selina Kyle made her debut as a jewel thief in 1940’s Batman #1 and has since gone on to star in several of her own solo series, controversially appeared in the bosomy New 52 relaunch and headlined one of the worst movies of all time. Despite all that, Catwoman is a femme fetale to the finish and a never ending frustration for both the Caped Crusader and his alter ego. In all her numerous incarnations, one thing’s for sure, the Cat will endlessly toy with the Bat, siding with him one minute, then tossing him aside the next, and doing it all according to her own rules.

Honorable Mention: Red Hood

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Everyone loves when a good guy turns bad, right? Take for example the former-Robin Number Two, Jason Todd, who, thanks to some help from Talia al Ghul and her father’s Lazarus Pit, comes back refreshed, renewed and revengeful after ruthlessly being crowbarred to death by the Joker. When Todd surfaces again, he takes the Clown Prince’s old moniker of Red Hood, and in an effort to avenge his own death, starts a one-man war against crime and corruption by trying to influence it from within. A true vigilante, Red Hood is pretty much what would happen if Batman forewent his no kill policy.

As a daily reminder of his greatest failure, Red Hood forces the Caped Crusader to think long and hard about some of life’s biggest questions, like, why does he keep letting the Joker kill his family, or should he try to control crime like Jason instead of hopelessly laboring to destroy it? Because even though the Red Hood hates Batman (for a while) and fights him time and again, there is a noble method to his murderous madness, which makes it hard to pin him as a straight villain. He’s an anti-hero, fighting crime on his own terms, which more often than not means blowing away Gotham’s worst with *gasp* guns. Rest assured, this won’t be the last we hear of Red Hood, since there’s a good chance he will be the focus of the next Batman movie.

Did we miss any of the Dark Knight’s more deserving villains? Do we have the order all wrong? Let us know in the comments.

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