From Pixar's toon megalomaniacs to Batman's favorite psychotic clown, the screen's best superhero-movie bad guys

20. Obidiah Stane, ‘Iron Man'

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Stane may be a bad person, but he's a good businessman. Jeff Bridges' industrial magnate from the first Iron Man movie was only thinking of the well-being of Stark Industries when he paid a terrorist cell to kidnap Tony and kill him in the Middle Eastern hinterlands. Not the best excuse in the world, but as manager of the company he built with Howard Stark, he's got shareholders to answer to. If a little extortion and secondhand murder is what it takes to keep the profit margin in the black, that's just the cost of doing business. And if he has to put his on his supersuit — that “Iron Monger” get-up — to make sure things go his way, well … welcome to corporate America in the 21st century. CB

19. Winter Soldier, ‘Captain America: The Winter Soldier'/'Captain America: Civil War'

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As Captain America’s faithful sidekick during their World War II days, Bucky Barnes (Sebastian Stan) was a chipper crimefighter, as dedicated to preserving the American way as his star-spangled best friend. Then the character got a cold-blooded edge when he was brainwashed after a presumed battlefield death — and my, doesn't that robot-armed killing machine known as the Winter Soldier look mighty familiar. In Civil War, he was a man divided between his forced hardwiring for terrorist outfit HYDRA and his abiding devotion to his do-gooding mentor. Rogers stuck by his old pal, but to many figures in Marvel’s world, the former (and future?) assassin is a kill-on-sight target. CB

18. Elijah Price, ‘Unbreakable'

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Much like the film in which he appears, Elijah Price is a bit underrated and misunderstood. Samuel L. Jackson's stricken, possibly deranged man is trying to convince an ordinary security guard named David (Bruce Willis) who just survived a fatal train crash that he may, in fact, be a superhero. M. Night Shyamalan’s follow-up to the box-office phenomenon The Sixth Sense is a divisive, imperfect thriller, but in Price the writer-director crafted a tragic character whose desire to fit in — he was born with extremely brittle bones, leaving him permanently fragile — results in a psychosis that allows him to believe he’s a supervillain. All Price needs is his nemesis, which leads to a friendship with David that has a lethal ulterior motive. We don’t realize that a monstrous evil has been hiding in plain sight throughout the film the entire time. TG

17. Toad, ‘X-Men'

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First introduced as one of Magneto’s “Brotherhood of Evil Mutants” in the original Sixties X-Men comics, this misshapen, high-jumping lackey was something of a afterthought in the Marvel Universe. It took badass martial artist Ray Park — the same Scottish actor who turned The Phantom Menace's Darth Maul into a samurai-like Sith Lord — to make this creep cool. Park energized the original X-Men movie with his gravity-defying leaps, super-stretchy tongue, and acid-tinged loogies, and changed the perception of the villain from old-fashioned to cutting edge. Suddenly, this creature seemed both grotesque and a genuinely agile threat. NM

16. Syndrome, ‘The Incredibles'

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People do bad things when they feel hurt, but that doesn't necessarily make them horrible people. In Pixar's The Incredibles, young but enthusiastic Buddy (voiced by Jason Lee) invents his own janky rocketboots in the hopes of playing sidekick to Mr. Incredible (Craig T. Nelson) — and gets coldly rebuffed by his hero. So it's understandable that he'd be a little resentful of the gifted super-types, though that doesn't make his plan to arm the population with extraordinary abilities any less tragic. His most iconic line is practically a call for help: “When everyone's super, no one will be.” Oh, the irony. CB

15. The Penguin, ‘Batman: The Movie'/'Batman Returns'

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One of the Caped Crusader's key rogues, the villain known for causing fowl play was originally associated with Burgess Meredith's pop-art version on TV and the show's 1966 feature-length Batman: The Movie version; his squawk was so distinctive that 50 years later comedians like Jon Stewart (who compared it to Dick Cheney) are still imitating it. Danny Devito brought a note of gothic tragedy to the character in 1992's Batman Returns, playing the Penguin as one of Gotham City’s unwanted children, back to seek revenge. He's the criminal mastermind who could’ve been Bruce Wayne, if only he’d been raised in a manor and not in the sewers. NM

14. Sabretooth, ‘X-Men'/'X-Men Origins: Wolverine'

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Poor Sabretooth was 10 names down the cast list in the original X-Men movie, a hirsute beast who operated with little success alongside Mystique and Toad as a mercenary henchman for Magneto's Brotherhood of Mutants. (A tip of the helmet to former pro-wrestler Tyler Mane, who imbues the killer with an animal savagery.) But the character got a significant upgrade in X-Men Origins: Wolverine, which cast Liev Schreiber as Victor Creed/Sabretooth and gave him a prime spot alongside Hugh Jackman's Wolverine as a half-brother of questionable allegiance. With his super-strength, razor-sharp claws, and rapid healing powers, Sabretooth is the good mutant's sinister flipside, — a relentless fighter who carved his way through the Civil War, both World Wars, and the Vietnam War, and keeps coming back for more. ST

13. Ronan the Accuser, ‘Guardians of the Galaxy'

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Marvel honchos Stan Lee and Jack Kirby were at the height of the “cosmic” phase of their Sixties Fantastic Four run when they created Ronan: an officer of an alien court who roams the universe serving as a one-man judge, jury, and executioner. So fanboys could tell the big-screen Guardians of the Galaxy was going to be something special when Lee Pace popped up as the “Accuser,” complete with his trusty, matter-displacing Universal Weapon. It’s not easy to translate the mad genius of a Kirby drawing into live-action, but the movie captures both the steely ferocity and the mind-blowing weirdness of one of comics' great deep-cut villains. NM

12. Ozymandias, ‘Watchmen'

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A calculating, ruthless mastermind whose evil plan is … world peace? Bringing the “end justify the means” principle to its most extreme conclusion, Watchmen's playboy biliionaire Adrian Veidt (Matthew Goode) decides that the only way to forestall nuclear annihilation is to stage an attack from an outside source. His utopian hope? That it’d unite feuding nations. A couple million dead is a brutal sacrifice, but is it really that much to lose for the sake of the Earth? Ozymandias is the most unsettling type of supervillain — the sort that makes you believe he might actually be on to something. CB

11. Bane, ‘The Dark Knight Rises'

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The knock on Tom Hardy's Bane is that he's woefully inarticulate: If Christian Bale’s Batman could be described as “gravelly,” then his nemesis has a whole quarry in his throat. Yet his actions speak louder than words. Amidst the chaos kicked up in Gotham City after the first two Dark Knight installments, Bane threatens to bring a dictatorial order that sharply contrasts with the nihilistic mischief-making of the previous movie's Big Bad. In this final chapter of Christopher Nolan's trilogy, the muzzled, muscular supervillain represents a New World Order of authoritarian rule supported by military thuggery, mass surveillance, and kangaroo courts. A more competent Trump, in other words. ST

10. Ultron, ‘Avengers: Age of Ultron'

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Hoisted by his own super-petard, Tony Stark had intended Ultron (a CGI'd-up James Spader) to function as a global peacekeeping force, but as intelligent robots are wont to do, the android quickly reasoned that humanity represented the greatest threat to Earth and set about eliminating them. Behold, then, the enemy of the second Avengers' movie — one so great he came with own era, per the title. More of an overzealous defense contractor than a villain per se, Ultron was simply carrying out orders. A little too well, some might say. CB

9. Ra’s al Ghul, ‘Batman Begins'

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Ra’s al Ghul appears first to Bruce Wayne as Henri Ducard, a wise mentor who not only offers lessons in stealth combat, but a way to channel the inchoate anger and thirst for vengeance that has led the young man to a dark place. As played by Liam Neeson, Ra’s al Ghul/Ducard makes an effective villain because he operates from the inside out, bonding deeply with Wayne over shared grief and loss while fiendishly manipulating him to embrace his worst instincts. In the crime-infested Gotham that killed his parents, the League of Shadows leader's plan to raze the city and start again is, to his apprentice, a serious temptation. ST

8. Doctor Octopus, ‘Spider-Man 2'

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Ever since Vic Frankenstein first went grave-robbing, scientists have tiptoed into ethically murky territory in pursuit of a breakthrough. In Spider-Man 2, Otto Octavius (Alfred Molina) built his distinctive mechanical-arm rig to contain a miniature sun, theoretically providing endless renewable energy for the people of New York. But he was so dead-set on his experiment working that ambition clouded his vision, turning to theft in order to fund his project. (Though the evil sentient computer chip in the arms may have also had something to do with that.) Over the course of the five blockbusters devoted to the webslinger, we've seen a lot of famous Spidey villains bring their sturm und drang to the screen. Doctor Octopus are the only ones the movies have given a soul to. CB

7. Mystique, Various ‘X-Men' Movies

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Rebecca Romijn gave audiences a memorable eyeful as the azure-skinned mutant Mystique in the original X-Men films, but Jennifer Lawrence has already supplanted her with a definitive take on the crafty shape-shifter in the reboot franchise. Lawrence’s Mystique grew up as the foster sister of Professor Xavier (Jams McAvoy) and helped found the X-Men, but defected due to ideological differences. Guided by self-preservation over any allegiance to the X-Men or even Magneto, she's has played both sides against the middle whenever it suits her. Cunning and deadly, she can knock down — or simply become — anyone standing in her way. CB

6. Lex Luthor, Various ‘Superman' Movies/'Batman v Superman'

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Lots of supervillains revel in their own evil, but few are as proud of their intelligence and wit as Lex Luthor. Memorably portrayed by Gene Hackman in Christopher Reeve's Superman movies with rakish charm and more than smidge of above-it-all haughtiness, Lex behaves as if he’s those films' true star — downright offended that the damned Man of Steel keeps interfering with his ingenious schemes. For him, wickedness is a rarefied art that’s to be admired — how could something as banal as heroism possibly compare? More than 35 years later, Hackman's knowingly self-regarding performance still haunts other actors' portrayals: Kevin Spacey basically pantomimed him for 2006's Superman Returns, and you can still see Jesse Eisenberg trying to channel him in Batman v Superman while attempting a fresh take on smug genius. TG

5. Catwoman, Various ‘Batman' Movies

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Lee Meriweather was far-out fun in Batman: The Movie (1966), Michelle Pfeiffer exuded kinky erotic heat in Tim Burton’s Batman Returns (1992), and most recently, Anne Hathaway lent Selina Kyle some wiles in The Dark Knight Rises (2012). (We're just going to collectively pretend that Halle Berry solo Catwoman flick from 2004 never happened, ok?) So who’s the top feline? Pfeiffer in a (cat)walk: the stitched-together S&M getup was an instant icon, and she evinced the perfect combination of demure and naughty as Batman's sometimes-friend, sometimes-foe, sometimes-friend-with-benefits. CB

4. Magneto, Various ‘X-Men' Movies

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The Malcolm X to Charles Xavier’s Martin Luther King, Magneto is militant mutant demanding change by any means necessary. In the original X-Men films, Ian McKellen rooted the metal-moving Erik Lehnsherr's extremism in memories of the Holocaust, while Michael Fassbender played the rebooted franchise's version as a ideological radical right at home in the turbulent Sixties and Seventies. Both characters are men committed to their principles, and willing to rationalize away whatever violence they must if that means a safer world for their Homo superior brethren. CB

3. General Zod, Various ‘Superman' Movies

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Of all of Superman's foes, General Zod is perhaps the most emotional for Kal-El — he represents a connection to a home to which he can never return. A fellow Kryptonian who was banished for life for treason by Jor-El, Zod wants to destroy the Man of Steel in part to get back at our hero's father. No wonder Superman II's fight scenes have extra gravitas to them: You constantly sense the deeper stakes going on in this battle between two survivors from a dead world. As played by Terence Stamp, Zod is all tightly coiled rage, controlled but deadly, which made him a perfect counterpoint to Christopher Reeve's square-jawed, earnest decency. For Man of Steel (2013), Michael Shannon upped the bug-eyed intensity, eschewing Stamp's aloofness and restraint to deliver a more purely unhinged performance. TG

2. Loki, Various ‘Thor' Movies/'The Avengers'

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Ladykiller Tom Hiddeston has made the Norse trickster deity into a fan favorite across a handful of scene-stealing appearances in the solo Thor solo pictures and as The Avengers' bringer of chaos and destruction. He's slick and debonair, using his powers of persuasion to wrest the throne of Asgard for himself. Granted, in Thor: The Dark World, Loki set aside his differences with brother to defend their home from the encroaching danger of some particularly nasty elves, and hinted at what a difference he could make as a hero. Alas, his instincts got the better of him and he returned to his God-of-Mischief ways. Frankly, we wouldn't want him any other way. CB

1. The Joker, Various ‘Batman' Movies/'Suicide Squad'

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With his mirthless smile and sarcastic verbal japes, the Joker both embodies the dark soul of Gotham City and stands apart from it, a deranged jester who uses whimsy and color as an playfully ironic cover for unfathomably sadistic plans. He's been a camp kingpin (Cesar Romero's giggly criminal in TV series and Batman: The Movie) and a psycho taken to Method-acting extremes (Jared Leto's over-the-top version in Suicide Squad). In Tim Burton's Batman (1989), Jack Nicholson widened the rictus of his shit-eating grin as his Joker asked the world to smile with him, unleashing a nerve gas that would cause the entire city to laugh themselves to death. And Heath Ledger’s Oscar-winning performance in The Dark Knight (2008) turned the Clown prince of Crime into a frightening, nihilist ghoul, a lone-wolf terrorist who wants to plunge Gotham into chaos for the sake of it. He is the villain of our times. ST

20 Best Movie Supervillains You Love to Hate