The Caped Crusader is back: On March 4, Robert Pattinson will become the seventh actor to don the cowl in a live-action film with The Batman. To prepare, join The Ringer this week as we navigate the grime of Gotham and explore the history of one of the most recognizable superheroes in the comic-book landscape.
A core principle of Batman is that he must fight crime—without it, there is no Batman. That also means that the criminals of Gotham City are just as important to the existence of Batman as Bruce Wayne. Villains have been a part of the story since the Caped Crusader’s inception, going all the way back to Alfred Stryker. But some members of the rogues’ gallery are better than others—a fact that’s become even truer since Batman hit the big screen.
Below, we rank the best villains who have gone toe-to-toe with Batman in film, from the delightful to the unforgettable to the truly terrifying.
25. Mr. Freeze (Arnold Schwarzenegger, Batman & Robin)
Batman & Robin is a campy mess that required Arnold Schwarzenegger to spend hours in a makeup chair every day, but he wasn’t about to allow all that to melt him down. In fact, he embraced his role in what’s essentially a $160 million, two-hour toy commercial—after all, no one is better equipped to portray a real-life action figure than Schwarzenegger. Mr. Freeze spends his scenes vamping and spouting ice puns. (Some favorites: “All right, everyone! Chill”; “Cool party”; and “Tonight’s forecast: A freeze is coming!”)
And while the late Joel Schumacher has apologized for how the movie turned out, Arnold doesn’t deserve blame for that. Unlike most everyone else on screen, he actually seems like he’s having fun. That’s just the stone-cold truth. —Alan Siegel
24. Holiday (Julie Nathanson, The Long Halloween)
The Holiday Killer (a.k.a. Holiday) is a more interesting foil for Batman in mystery than in reveal, but let’s give it up for the mystery: A serial killer gruesomely murders a member of one of Gotham’s warring crime families on every major holiday, starting with a mob nephew who was about to rat out his own family’s operation. Right there you’ve got the ticking clock—one that looms over the investigation as Batman attempts to reverse-engineer the identity of Holiday based on their victims. Throughout The Long Halloween, we see and hear very little of Holiday; what makes the character effective is what the string of killings does to Gotham and Batman himself, who slips into existential crisis as he flails about from one suspect to the next. A stifled, frustrated Batman is par for the course in these stories. Yet Holiday is the only villain who has made Batman, in his mounting desperation, repeatedly visit Arkham to consult with Calendar Man (Calendar Man!) à la Hannibal Lecter. Scarier yet: It actually plays. —Rob Mahoney
23. Mr. Freeze (Michael Ansara, Batman & Mr. Freeze: SubZero)
There are tiers to Batman’s rogues’ gallery. The heavy hitters—Joker, Two-Face, Ra’s al Ghul, Scarecrow—work best because they reveal something deeper about Batman’s psyche. Like Bruce Wayne, these characters weren’t born with superpowers or predestined to save planets. Instead, they’re deformed or brutalized by a chaotic world and choose to enact their specific brand of justice upon it. Often these characters reveal something psychological about the Dark Knight. In comparison, your Poison Ivys, Clayfaces, and Killer Crocs of the world belong to the second tier of villains. Unless handled with care, their otherworldly powers transform Batman from a deeply complex hero into just another comic-book character fighting some weirdos.
Mr. Freeze belonged to the latter category until Batman: The Animated Series and 1998’s Batman & Mr. Freeze: SubZero transformed the villain into a tragic figure. Voiced by Michael Ansara, the animated Freeze was imbued with a sense of Shakespearean grandeur. The introduction of Nora Fries gave him an overarching purpose that most comic-book villains lack. Freeze and Bruce Wayne are similarly driven by a need to conquer death; it’s a lot easier to sympathize with a villain who has a glass tube over his head when his motivation is as pure as being a very sincere Wife Guy. If Matt Reeves is serious about casting Mr. Freeze as the next villain in his Batman franchise, he could do a lot worse than mining Batman: The Animated Series for inspiration. —Charles Holmes
22. The Joker (Cesar Romero, Batman)
For every era of Batman there’s been a Joker tailor-made to suit both the time and the Bruce in question. The Joker was originally conceived as a stone-cold psychopath, but the puritanical Comics Code Authority sanitized Gotham on the page in the ’50s and ’60s. The silver lining: That inspired the very campy, family-friendly Cesar Romero version of the character in both the TV series and 1966’s Batman. This clown prince has all the trappings of other Jokers—the purple suit and green hair are intact—without any of the deadlier ramifications. Romero’s Joker was nonetheless highly influential—you can hear his rounded vowels and theatrically rolled consonants in Mark Hamill’s voice-over work. But what gave this Joker his menace even in a kinder, gentler Gotham was Romero’s insistence that he keep his famous mustache under the white pancake makeup. The visual result is, frankly, terrifying and provides some genuine chills in an otherwise toothless era of Batman. —Joanna Robinson
21. Hush (Geoffrey Arend, Batman: Hush)
A great villain meets a hero where they live, and contrary to the Gotham of it all, Batman lives pretty squarely in his own head. Hush preys on that idea by backing the World’s Greatest Detective into a corner from the start, with every angle worked out in advance. The information imbalance is striking. Batman doesn’t know who Hush is, where he came from, what he wants, or even what he looks like beneath his bandage-wrapped face. Hush, meanwhile, works the leverage points of every other villain and has Batman’s secret identity already worked out from the jump. He puppets Bane to draw Batman out in the open, then severs the line on his grappling hook mid-flight. He makes pawns of Poison Ivy and, by pheremonal extension, Superman just to inch his master plan forward. It’s a framing that makes some of the best-known figures in Batman’s rogues’ gallery feel small. Hush is even one step ahead of the die-hard fans. His most thrilling deception is that even if you think you know this character and this story—you don’t. —Mahoney
20. Max Shreck (Christopher Walken, Batman Returns)
Sure, Catwoman and the Penguin do bad things in Tim Burton’s delightfully grotesque Batman sequel, but Max Shreck is the movie’s true villain. Christopher Walken, sporting flowy white hair, plays a filthy-rich industrialist who wants to build a power plant in the heart of Gotham and, to his credit, Burton understands that the ruthless power broker with a failson named Chip deserves a hell of a lot more scorn than his flipper-armed accomplice.
In addition to having no qualms about poisoning the city’s residents with toxic waste, Shreck attempts to silence his receptionist Selina Kyle by pushing her out a window. In the end, Catwoman gets her revenge, killing Shreck with a fittingly brutal, taser-enhanced kiss. It may be the best death scene in any Batman movie. —Siegel
19. The Joker (Zach Galifianakis, The Lego Batman Movie)
It may be called The Lego Batman Movie, but the 2017 film is, at its toy heart, the story of its Joker. Played with hearty, wounded volatility by Zach Galifianakis, Lego Joker applies red lipstick like he’s in a Soundgarden video; describes his bod as “too much flab, not enough ab”; complains about the good-for-nothin’ henchmen who surround him; and above all else longs desperately and openly to be mutually respected by his greatest adversary, Batman, a wish that takes him from Gotham City to the Phantom Zone and back. “What we have—this is special!” he pleads during one fight scene; Batman’s “You mean nothing to me” response is delivered with “I don’t think about you at all” dispassion. Unpredictable and insecure, larger than life and only a couple of inches tall, Lego Joker wears his cold heart on his sleeve and just wants to feel seen. And really, don’t we all? —Katie Baker
18. The Riddler (Frank Gorshin, Batman)
Adam West’s Batman faced off against a murderers’ row of villains in 1966’s Batman, but despite such heavy hitters like Catwoman, the Joker, and the Penguin in the mix, it’s Gorshin’s giggling Riddler who keeps the whole thing moving at a frantic pace. Gorshin was known primarily as a comedic impressionist and occasionally as a hard-boiled gangster—he brought both talents to his green-spandex-clad Riddler. The trademark Gorshin giggle is one he lifted from Richard Widmark’s killer in Kiss of Death (1947), who was in turn based on the Joker. But whatever unsettling bits and pieces Gorshin borrowed to build his villain, the end result is all his own. A trickster full of puzzles meant to keep the World’s Greatest Detective guessing, Gorshin’s Riddler is the only character from the ’60s TV show to earn an Emmy nomination. Not bad work for a cheesy comic-book villain. —Robinson
17. Poison Ivy (Uma Thurman, Batman & Robin)
I am, admittedly, a single-issue villain voter on this subject. “How fly is this villain?” I ask myself when watching any superhero movie. “Flyer than fuck,” Poison Ivy answered back in 1997’s Batman & Robin. She is head-to-toe latex, was hot-gluing appliques to her face before those Euphoria girlies were even a twinkle in Mother Nature’s eye, and her venomous vapors keep the Bat-boys absolutely tripping. Simply put: That girl is poison. And she’s got a doctorate.
The Batman franchise isn’t exactly known for its fashion, its dynamic color palette, its lewks—but played by Uma Thurman, Ivy is like if The Real Housewives of Beverly Hills’ Dorit Kemsley drank too much Chanel No. 5 and suddenly became a comic-book villain. Her zingers may not always land, she may have terrible taste in bullish men, and her weird accent might be absolutely unplaceable—but when it comes to glam, Poison Ivy does not miss.
Is Poison Ivy a gal’s gal? No, she is not. She straight-up murders Mrs. Freeze, and Batgirl gives her a real second-wave feminism talking-to about it. But Poison Ivy is a gal’s villain. And in the battle to save the planet from the likes of “the militant arm of the warm-blooded oppressors, animal protectors of the status quo,” there’s only one ally necessary: Miss Mother Nature. —Jodi Walker
16. Red Hood (Jensen Ackles, Batman: Under the Red Hood)
Red Hood is one of the most popular animated Batman villains in recent history—particularly the version voiced by Ackles in 2010. He represents the dark side of Batman, showing us just how dark the Dark Knight could be if he went all the way and killed those he fought. He also shows us—and Bruce—what happens when Batman fails one of his protégés. While Dick Grayson represented an evolved and lighter side of Bruce, Jason Todd is the opposite side of the coin; the embodiment of Batman going too far and surrendering to the brutality around him. —Arjuna Ramgopal
15. Talia al Ghul (Marion Cotillard, The Dark Knight Rises)
Talk about playing the long game! By the time she first comes face-to-semi-masked-face with Bruce Wayne in The Dark Knight Rises, Talia al Ghul, the daughter of Ra’s played by Marion Cotillard, has spent the better part of her past decade plotting revenge against the man who left her father to die. She has adopted the business lady persona of Miranda Tate; she has amassed corporate influence at Wayne Enterprises; and she has thrown the party at which she finally connects with the reclusive Gotham icon. (Later, she finally connects with him.) By the time she ultimately reveals her true identity to Batman (an origin story involving The Pit and the kindness of … Bane?!), it has been forever in the making. “You see, it’s the slow knife,” she says, knifing him, “the knife that takes its time, the knife that waits years without forgetting, then slips quietly between bones … that cuts deepest.” If only her own abrupt death a few minutes later were as satisfying a twist. —Baker
14. Harley Quinn (Arleen Sorkin, Batman Beyond: Return of the Joker)
The Batman Beyond series is a departure from the kind of story that fans normally expect when they think of the Caped Crusader. Even so, Return of the Joker gave fans a classic villain in Harley Quinn. Played by voice actress Arleen Sorkin, who also voices Quinn in Batman: The Animated Series, Harley is brought to life for the first time in a feature length film. She plays a small but pivotal role in the film, but as the years have gone on, her presence has been amplified—now Harley Quinn is a part of the bigger DC Comics foundation. Of all the shows that originated on the now-defunct DC Universe streaming service, Harley Quinn is the best of them all (yes, even better than my beloved Young Justice). Freed from the shackles of being the sidekick or relegated to flashbacks, she stands on her own two feet and shows everyone—from Batman to the Joker—what they’ve been missing. —Jomi Adeniran
13. Two-Face (Tommy Lee Jones, Batman Forever)
With its caked-on makeup and cackling, Tommy Lee Jones’s 1995 performance of Two-Face, the villain born out of a mobster acid-throwing attack on former district attorney Harvey Dent, is not subtle. When we meet the character he is flipping a coin and hissing lines like: “Maybe, maybe not. You could say we’re of two minds on the subject.” But exactly none of Joel Schumacher’s Batman Forever is subtle, and within the context of its cartoonishly loopy universe (and with the passage of time), Two-Face is actually pretty fun!
He rolls with angelic and devilish assistants named Sugar and Spice, played by Drew Barrymore and Debi Mazar. There is a whole YouTube compilation called “Goofy Two-Face” of his one-liners and maniacal laughs. His hair is half spray-painted purple as if he’s a middle-schooler about to go trick-or-treating. Speaking of which, it does remain irritatingly unexplained how the acid splash created such symmetrical scarring, but [extremely TLJ voice] come on, let’s not split hairs here, OK? —Baker
12. The Riddler (Jim Carrey, Batman Forever)
Long before Paul Dano’s Riddler in The Batman, there was the one and only Jim Carrey. At the height of Carrey’s superstardom in the ’90s, the comedic actor joined a star-studded cast alongside Tommy Lee Jones, Nicole Kidman, and Val Kilmer in 1995’s Batman Forever. And while Joel Schumacher’s film was a sizable dropoff from the previous two Tim Burton–directed movies, Carrey—and all of his brilliant chaotic energy—remains one of its few bright spots.
Carrey is simply himself in Batman Forever—or simply Ace Ventura, or Stanley Ipkiss when he puts the mask on—and that humor translates seamlessly to an often cartoonish villain with a name like Edward Nygma who fights Batman with, you know, riddles. Who doesn’t want to watch Jim Carrey don a tight green jumpsuit—along with an equally tight silver jumpsuit, bedazzled with rhinestones—and shout things like “joygasm”?
There are so many things that make no sense in this ridiculous but fun movie. And yet there’s no question that Carrey was the perfect fit for it. —Daniel Chin
11. Harley Quinn (Margot Robbie, Suicide Squad)
OK, we’re breaking our own rules a bit here: Margot Robbie’s Harley Quinn has yet to appear in an actual Batman movie. In fact, she’s barely even interacted with Batman. But it would’ve felt wrong to omit a rendition so captivating that it emerged from the ashes of an absolute flop to stand alone in a highly underrated spinoff flick, so we’re considering that brief scene in Suicide Squad as qualification enough. Historically, Harley has been tethered to the Joker, and while Robbie’s arc isn’t completely divorced from the clown, it is proof that she doesn’t need his (in this case) sorry, knife-obsessed ass. In Suicide Squad and Birds of Prey, Robbie is undeniable—zany, endearing, twisted, and recklessly destructive. She makes you root for her—whether the mission at hand is killing a sorceress or acquiring a breakfast sandwich. —Andrew Gruttadaro
10. Phantasm (Dana Delany, Mask of the Phantasm)
The dark alter ego of Andrea Beaumont might be one of the most criminally underrated villains introduced in the Batman animated film Mask of the Phantasm. One of Bruce Wayne’s most notable love interests, she acts as a counterweight and one of the biggest foils to his early quest for vengeance and crime fighting. A gray phantom of the night that can disappear in a cloud of smoke and strike fear into all, she’s on the right side of justice but the wrong path, according to Batman. And amid that tug-of-war, she offers a philosophical challenge that reverberates through all Batman tales. “What will vengeance solve?” Bruce wonders aloud, to which she simply replies: “If anyone knows the answer to that, it’s you, Bruce.” —Steve Ahlman
9. Ra’s al Ghul (Liam Neeson, Batman Begins)
Before his late-stage emergence as an action hero waging war with various modes of transportation, Liam Neeson had become a go-to actor for mentor roles, whether he was playing Jedi Master Qui-Gon Jinn in The Phantom Menace or voicing Aslan the Lion in The Chronicles of Narnia. Initially, Neeson’s appearance in Batman Begins as Henri Ducard fit the mentorship mold, as he takes a young Bruce Wayne under his wing and teaches him how to become a stealthy ninja with a flair for theatricality and deception. Alas, Henri Ducard was really Ra’s al Ghul, the leader of a shadowy organization with a draconian sense of justice that intended to destroy Gotham from within. That Bruce yearned for a father figure after losing his parents made Ra’s deception sting that much harder: the first of many difficult lessons in his journey as Gotham’s savior. Ra’s might’ve perished at the end of Batman Begins, but his desire to purge Gotham—and his open question about whether the city is even worth saving—resonates throughout Christopher Nolan’s trilogy. —Miles Surrey
8. Scarecrow (Cillian Murphy, Batman Begins)
I’d go as far as to say that it was an act of courage to try to bring to life one of the wackiest, B-tier villains in the Batman lexicon. Scarecrow’s use of fear toxin and his tormenting of Batman leads to fun results in both the comics and recent video games, but using him in a mostly grounded Christopher Nolan film still reads like a stretch. But Cillian Murphy pulls off a menacing Dr. Crane who, in unforgettable moments, steps into the more horrific elements of Batman lore. Also, it’s worth noting that he’s the only villain to span all three Nolan films. Long live this slippery little bastard! —Ahlman
7. The Joker (Jack Nicholson, Batman)
With all due respect to Cesar Romero’s portrayal of the Clown Prince of Crime in the 1960s, the Joker was not exactly seen as a prestige role when Jack Nicholson was cast in Tim Burton’s 1989 film Batman. And why should it have been? The idea of imbuing a green-haired, purple-clad clown with menace seemed foolish, if not antithetical to the character’s cartoonish on-screen origins. Even Nicholson worried about it: “I was afraid because of my feel of the television series and the way movies tend to be done and talked about, I didn’t want this to go through the normal ‘let’s brighten this up for the kids!,’” he said once.
But that wasn’t Burton’s goal for the Joker, and in Nicholson, he found a willing coconspirator. Sure, Nicholson’s work as a low-level gangster turned supervillain had its share of ridiculous moments—some iconic, like the Joker and his goons’ destruction of the art museum—but the three-time Oscar winner brought the same terror to the role that he did Jack Torrance nine years earlier. The goal was to entertain, but also to frighten, and it certainly worked. Like Burton’s film, Nicholson’s Joker was a massive success (and a huge financial windfall for the actor). It also set the character up to be an award-bait magnet decades later: If Nicholson hadn’t donned the facepaint, we likely wouldn’t have gotten Heath Ledger’s turn in 2008, nor Joaquin Phoenix’s in 2019. We’ve perhaps gotten a little too far from Romero’s Joker—do we need to know how he fits into Jungian and Hobbesian philosophies, or do we just need for him to find creative ways to antagonize Bruce Wayne? But Nicholson’s performance remains pitch perfect—a bridge between the character’s campy beginnings and its why so serious present. —Justin Sayles
6. Two-Face (Aaron Eckhart, The Dark Knight)
Few superhero movies have effectively employed more than one antagonist without it becoming a distraction, and The Dark Knight pulls it off better than any of them. That’s perhaps because, for the greater part of the film, Eckhart’s Harvey Dent is a hero—one who doesn’t need to hide behind a cowl to be Gotham’s symbol for justice and hope. Joker is, of course, The Dark Knight’s main attraction, but as he steals scenes with his mesmerizing presence throughout the movie, Harvey is quietly losing his grasp on his identity as the city’s white knight.
Even before Harvey had half of his face burned off, Joker’s war against Batman and Gotham was slowly pushing him into becoming Two-Face. His final transformation is both terrifying and tragic, and it ultimately ties the entire film together as he stands off against Batman and Commissioner Gordon while holding Gordon’s family hostage. While Heath Ledger’s Joker will always be The Dark Knight’s best-remembered performance, Eckhart brilliantly plays a crucial complementary role, and Harvey’s descent into madness serves as the soul of the story. You either die a hero, or you live long enough to see yourself become the villain. —Chin
5. Bane (Tom Hardy, The Dark Knight Rises)
Sure, his performance inspired an entire parody in an animated series, but take nothing away from Tom Hardy’s Bane: He goes hard in The Dark Knight Rises. When he wasn’t beating the ever-living shit out of Batman—and lest we forget, he broke the dude’s back without breaking a sweat—Bane delivered an endless stream of savage quotes that were all the more memorable because they were coming out of the muzzled mouth of Sean Connery trapped in a WWE superstar’s body. (My personal favorites: “The shadows betray you because they belong to me,” and, “Now’s not the time for fear; that comes later.”) No other villain pushed Batman to the brink quite like Hardy’s Bane, who has stood the test of time thanks to his incomparable physicality—and equally impressive memeability. —Surrey
4. The Penguin (Danny DeVito, Batman Returns)
He lives in the dingiest sewers you’ve ever seen. He eats black goo. He reacts to a man’s putdown by biting his face and exclaiming, “It could be worse … my nose could be gushing blood!” The beauty of Tim Burton’s Batman Returns is how deliriously unbeautiful it is: a strange and disgusting take on a superhero film that feels subversive even though, at the time, there were hardly any tropes to subvert. And Danny DeVito’s Oswald Cobblepot is the ambassador of that grotesquerie. “Penguin was a gift because it was very operatic and I like to go big,” DeVito told me in 2019. “That was like, hmm, that was fun.” He certainly went big, but the thing is, watching Batman Returns you can also tell that DeVito was having fun. Maybe that’s why, three decades later, he still stands as one of Batman’s most memorable nemeses. —Gruttadaro
3. The Joker (Mark Hamill, Batman: The Killing Joke)
While the Joker has had several iconic live-action portrayals over the years, there is only one true voice behind the animated version of the Clown Prince of Crime: Mark Hamill. The actor may have become famous for his on-screen heroics in a galaxy far, far away, but his talents truly lie in voice acting. After first lending his vocal cords to the iconic Batman: The Animated Series beginning in 1992, Hamill went on to voice the Joker in animated movies like Batman: Mask of the Phantasm and Batman Beyond: Return of the Joker, as well as the critically acclaimed Batman: Arkham video game series.
Hamill plays Joker’s laugh as if it were a musical instrument, shifting its tone and cadence to the tune of the infamous villain’s volatile moods. The results are as terrifying as they are entertaining. Part of the beauty of the animation medium is the almost limitless visual opportunities it affords, and in Batman’s animated run, the Joker—with all of his absurd antics—has been brought to his wildest potential. Hamill fully embraces the role, swerving between Joker’s blind rage and dark humor on a whim. He simply brings the cartoon clown to life better than anyone. —Chin
2. Catwoman (Michelle Pfeiffer, Batman Returns)
Catwoman has been causing problems for Gotham, Bruce Wayne, and Batman since the very beginning of the franchise. But no performance has captured the fractured nature of that assault better than Pfeiffer, who delivers a vengeful secretary, a woman in love, and a vinyl-clad, whip-happy dominatrix cat all in the span of one movie. Selina Kyle’s righteous crusade taken too far is classic Catwoman—a character who slinks in and out of the moral shadows like no other. Batman Returns turns her character’s duality into the perfect match for Bruce’s own. She shoves her claws underneath Batman’s unyielding armor and very nearly drags him into the darkness with her. You can feel every part of him wanting to follow. Like Eartha Kitt’s before her, Pfeiffer’s sultry delivery positively reinvents the word “meow,” and she pulls all of this off in an iconic, skin-tight, stitched-together costume that unravels with her mental state. Pfeiffer’s character was so popular in test screenings that her silhouette was inserted into the end of the movie to leave the door open for a spinoff movie that never materialized. Selina may be gone by the end of the film, but you can tell that Michael Keaton’s Batman will never forget her. —Robinson
1. The Joker (Heath Ledger, The Dark Knight)
Could it be anyone else? The Dark Knight’s expansive influence has shaped not just superhero blockbusters, but how the Academy hands out Best Picture nominations—and the key to its iconic status is its villain. As played by the late Heath Ledger, The Dark Knight’s Joker is a true agent of chaos—someone as liable to take out other members of Gotham’s criminal underworld with pencil tricks and creepy (and likely fabricated) monologues about childhood as he is to torment Batman. The best thing that can be said about Ledger’s performance is that the posthumous Oscar and enduring legacy as the greatest superhero movie villain of all time does nothing to flatter him. Fourteen years on, Ledger’s Joker remains as inscrutable, engrossing, and terrifying as ever. —Surrey