Given his rich, 79-year legacy across comics, radio, movies, and television, whittling down a list of the best Batman villains to only five is an extremely difficult task. After all, compared with a significant number of his superhero colleagues, Batman is often singled out as having the absolute best collection of villains to draw from in the entire history of superhero stories.
Thankfully, as a former comic book retailer and general commentator on masked heroes for well over a decade now, it’s a task I’m up for. While there are likely to be some omissions that people may find surprising, the sheer vastness of Batman’s rogues’ gallery requires an unusually blunt instrument to forge that enormous character list into an article like this one.
On that note, one key omission people will likely notice is Catwoman. Why? Because, in addition to defining herself as far more of an ally to Batman than an enemy over most of the last 20 years, Selina Kyle and Bruce Wayne are about to get married in an upcoming issue of Batman due this summer. Some readers may not care about that, but then again, if putting your wife or girlfriend on an “enemies list” sounds like a good idea to you, I don’t think I can help you.
So, without further ado, here are the five best Batman villains in the character’s long, illustrious history, from someone who calls Batman his favorite character in all of fiction.
5) Poison Ivy
First appearing in 1966’s Batman #181 and temporarily turning the Dynamic Duo against each other, Poison Ivy has been a constant thorn in Batman’s side. Though her appearances outside the source material aren’t as well-regarded as some of her major comic book arcs, Neil Gaiman, one of comics’ greatest modern writers, gave her a far more understandable and tragic beginning in 1988’s Secret Origins #36.
Initially a promising young botanical biochemistry student under the watchful eye of Dr. Jason Woodrue, Pamela Lillian Isley was victimized by her professor, who took advantage of her shy disposition to seduce her. Unfortunately, this led him to experiment on her, injecting her with poisons, toxins and mutated plant DNA that fundamentally altered her body chemistry, nearly causing her death.
Woodrue fled from the authorities and, eventually, Isley settled with her boyfriend in the Pacific Northwest. When he died from a mysterious fungal infection, her softer, more shy and easy-going exterior hardened and she decided to resettle in a new city full of possibilities, away from her pain: Gotham.
While other major villains would face our hero later in his career, Ivy actually encountered Batman within his first year on the job. After realizing the full potential of the power that resulted from the experiments performed on her, Ivy tried to hold the city hostage by threatening to release a dangerous set of poisonous spores into the air. Fortunately, a rookie Batman was able to stop her.
Ivy represents a threat to both Batman and Gotham City that’s very difficult to defeat. In the years since, her perspective on humanity as the world’s lesser form of life has led to calamity and atrocity, and the sheer danger that she embodies easily makes her one of Batman’s deadliest foes.
4) The Riddler
The king of criminal conundrums, Edward Nygma is, at first glance, one of Gotham City’s more whimsical villains. Unfortunately for Batman, his total lack of impulse control and chronic desire to prove his own mental superiority at any cost has, over the decades, transformed him from a goofy puzzler into a legitimately threatening menace, landing him a spot on our list of best Batman villains.
Particularly since DC Comics instituted their continuity alteration known as “The New 52” in 2011, the Riddler has become something of a foundational Batman adversary. He was the primary enemy in “Zero Year,” the story by Scott Snyder and Greg Capullo that reshaped Batman’s origin story for the modern era, and recently featured in a very prominent tale in the current Batman title called “The War of Jokes and Riddles” that saw him try to dominate the criminal landscape of the city.
That’s not to say that Riddler hasn’t been one of the key villains in Batman’s rogues’ gallery. While it took some time after his first appearance in 1948’s Detective Comics #148 to gain some traction, Riddler’s place in Batman’s wider legacy was galvanized by the unforgettable performance of actor Frank Gorshin during the three-season run of the original Batman television series. Ever since then, Riddler’s place has always been in the upper echelons of Gotham City’s underworld, and modern comics fans got a true taste of what the character is capable of in the modern classic comic book story “Hush” by writer Jeph Loeb and artist Jim Lee.
For perhaps the most efficient look at the threat represented by the Riddler, though, you can’t go wrong playing the Batman: Arkham video games, which spotlights the manic obsessiveness of the villain in a whole new light.
3) Ra’s al Ghul
Next on our list of best Batman villains, one of his most complicated relationships – especially nowadays – is with the legendary “Demon’s Head” and ruthless leader of the League of Assassins. While a significant number of Batman villains have been created on a ridiculously consistent basis since 1940, very few of them outside of the most well-known characters has managed to stick in the mythology. If a creator is lucky, one villain for every subsequent decade will manage to make an impression and stay for the long haul on Batman’s long list of enemies.
In the 1970’s, that villain was Ra’s al Ghul.
First appearing in Batman #232, from the now-legendary creative team of writer Denny O’Neil and artist Neal Adams in 1971, Ra’s immediately made himself known as a formidable adversary for the Dark Knight, both mentally and physically. He’s also one of the few Batman villains who can give the vast personal fortune of Bruce Wayne a literal run for its money. Ra’s’ resources as the head of a vast, nearly cult-like criminal empire make him one of Batman’s most undeniably dangerous enemies.
One of the things that makes Ra’s so cunning is his genuine respect for Batman, whom he often dryly refers to as “the Detective.” In fact, in the first stories featuring Ra’s, he first attempted to recruit Batman into the League of Assassins. Ra’s wanted the peak of physical and psychological perfection – Bruce Wayne – to marry his beautiful daughter Talia, create a new dynasty, and inherit the League of Assassins. When it became clear to Batman exactly how Ra’s envisioned the future of the world – namely, subservient to the League and to him – Batman refused to have any part of it, and with that refusal, a mortal rivalry for the ages was created.
As comics fans now know, things have only gotten more complicated for this relationship, since Ra’s and Bruce are now united by blood – namely, the blood of Bruce’s biological son, Damian. After taking advantage of a roofied Bruce Wayne, Talia acquired his genetic material to create the son he would not give her willingly. The result is a unification of the Wayne and al Ghul bloodlines in the form of Damian Wayne. Unfortunately for Talia and Ra’s, mistreating Damian during his childhood led him to discover what it means to be loved for who you really are in the waiting arms of his father and the likes of Alfred Pennyworth, Dick Grayson, Tim Drake, and Barbara Gordon. Because of this – among a few other things – Damian renounced his association with the League of Assassins and now proudly fights alongside his father as the incumbent Robin, the Boy Wonder.
Not only is Two-Face one of Batman’s most vicious villains, but he also represents something that Batman isn’t often confronted with every time they come face-to-face: one of his profound failures.
First appearing back in Detective Comics #66 from 1942, Two-Face is one of the few other original characters made by the same team that created Batman himself: writer Bill Finger and artist Bob Kane. With only a handful of appearances in the 1940’s and 50’s, the largely campy climate surrounding Batman due to the onslaught of the 1960’s TV series saw the dichotomous villain set aside in favor of more “kid-friendly” bad guys.
While he regained a degree of prominence due to both his unsettling appearance in Frank Miller’s tour-de-force The Dark Knight Returns in 1986 and his tragic origin depicted in Batman: The Animated Series in 1992, it would be a few more years before the man once known as Harvey Dent would realize his true potential in the source material in 1998’s Batman: The Long Halloween. Harvey Dent was Gotham City’s extremely promising and crusading district attorney, committed to cleaning up the rampant corruption brought about by the infection of organized crime at all levels. He also wasn’t afraid to become involved in an extra-legal triumvirate consisting of he, Gotham Police Captain James Gordon, and a certain masked vigilante. Unfortunately for Dent, when ready to put away noted crime boss Sal Maroni, Maroni flung a corrosive acid into Dent’s face right in the middle of a Gotham courtroom, scarring Dent physically and pushing his fragile psyche to the breaking point.
Totally surrendering to the freedom of chance, Two-Face used his extensive experience as an anti-crime crusader to quickly become one of the most powerful and effective super-criminals in Gotham, and definitely one of the greatest Batman villains. A far more personal adversary for both Batman and now-Commissioner Gordon, Two-Face represents a tragic fall from grace that would make even ancient writers of Greek tragedy envious. Much of that tragedy is depicted differently, though very effectively, in the now-legendary 2008 film The Dark Knight, starring Aaron Eckhart as Dent.
1) The Joker
Honestly, was there ever any doubt?
What is there to say about the greatest supervillain, not just in Batman’s rogues’ gallery, but ever? There is something that is deeply, fundamentally unsettling about the Joker. Very similarly to the way that Batman operates in the darkness — like a criminal — but is a virtuous man, the Joker represents the opposite conception. He thrives in the light, in front of the biggest audiences he can possibly command, with a rictus grin that masks the horror lurking just below the surface of his shining yellow teeth.
First appearing in 1940’s Batman #1, the Joker has often been hailed as one of the most singularly fascinating fictional characters to ever originate from the pages of comics. Legendary Batman writer and editor Denny O’Neil, creator of Ra’s al Ghul, once said of him, “I would submit that the Joker is the greatest trickster character ever,” going on to say that the Harlequin of Hate’s worldview stands in stark contrast to Batman’s representation of the triumph of rationality. DC Comics co-publisher Dan DiDio stated a belief that because the Joker is often random and haphazard in the way that he commits crime, and because Bruce Wayne himself was a victim of random crime, the Joker represents everything that Batman hates with all of his being.
Still, it takes more than that to rise to the role of the most definitive adversary — by far — that Batman faces off against. Part of it comes from the fact that the best stories featuring this conflict, whether in comics like “Joker’s Five-Way Revenge” or “Death of the Family,” or in movies like Mask of the Phantasm or The Dark Knight, show that these two extreme personalities have a bond that goes beyond just “hero versus villain.” In a lot of ways, you can likely say that each knows the other equally well, with a strange, intimate understanding of what makes each other thrive and fail.
In a weird way, the Joker adores Batman. The Dark Knight is the only one in the world who understands how the Joker’s mind works, and on more than one occasion the murder and mayhem caused by the Clown Prince of Crime has been described as an expression of that kind of twisted, evil affection that the Joker has for our hero. As for Batman, his own perspective on the Joker is likely summed up best through the words of writer Scott Snyder in 2012’s Batman #15. In that issue, Batman sees his longtime enemy in one of the most terrifying ways he’s ever been envisioned, and thinks to himself,
“Look into his eyes and tell yourself he’s just a man. Tell yourself he can’t know the things he says he does. He can’t know your fears. […] And his eyes…you have studied the human eye. There are six eye movements that reveal motive, then fifteen variations of each one. On everyone else you face — even the most hardened criminals — the pupils contract or expand depending on emotion. Happiness, laughter, affection. The pupils open. Fear, anger, hatred. The pupils close.
“But not his. His pupils stay fixed, tiny points of blackness, the eyes of someone who hates everything, everyone. Eyes that let in no light, that see through the darkness, stare into you, each pupil a tiny black pearl fixed in space. A bullet coming at you. Eyes that say he’s more than a man, eyes that say he knows you. No…you know what he is. Tell yourself the truth. He’s just a man who fell in a vat of chemical waste. He’s just a man…”
Bruce Wayne once said to a criminal on the street, “You have no idea what my nightmares are like.” Given everything Batman has seen and experienced, that may be true. Still, if you guessed that some of them include a murderous, psychopathic, and horrifying clown with no empathy whatsoever, I know I certainly wouldn’t bet against you.