1 of 16
15. Bullseye, Daredevil
Ben Affleck's first superhero movie is a leather-and-raindrops mediocrity. There's not much to like about it. Actually, there's only one thing to like about it: An immediately pre-fame Colin Farrell, clearly having a blast going miles-over-the-top as the assassin Bullseye. Farrell's gutter-grunge performance has very little to do with the comic book Bullseye. But at least he's having fun.
2 of 16
14. Doctor Octopus, Spider-Man 2
The movie never quite figures out whether Alfred Molina's Doc Ock is a full-blown mad scientist or just a nice guy driven toward evil by his own creation. But the character is without a doubt the best visual creation of the Sam Raimi Spider-Man trilogy. His four sinewy robo-limbs simultaneously suggest slapstick cartoons, Roger Corman B-movie monsters, and mid-'80s body horror.
3 of 16
13. Jean Grey/Phoenix/Dark Phoenix/Whatever, X-Men: The Last Stand
Several thousand mistakes had to be made for the third X-Men movie to be so terrible. But the threequel's biggest sin was squandering the Dark Phoenix saga, one of the best X-Men stories of all time, by mishmashing it in with several other plot lines. But give credit to Famke Janssen, who clearly relished unleashing the malevolent id of proverbial nice-girl Jean Grey. Right actor, right character, wrong movie.
4 of 16
12. The Joker, Batman
Nothing about Jack Nicholson's Joker is subtle, and the years since have retroactively made his clownish turn look like shtick. (Besides About Schmidt, Nicholson basically never stopped playing the Joker.) But Nicholson's scenery chewing makes the perfect foil for Michael Keaton's recessive caped crusader.
5 of 16
11. Red Skull, Captain America: The First Avenger
After The Matrix and Transformers, Hugo Weaving further minted his status as the go-to blockbuster-movie villain, playing the mad-genius über-Nazi Red Skull in the WWII era The First Avenger. The Skull is more two-dimensional and less complicated than some of the villains on this list — he's basically Conrad Veidt in Casablanca with nasty makeup — but that sits nicely in the film's tone of gee-whiz retro-jingo.
6 of 16
10. Mystique, X-Men franchise
There's not much to Mystique, really. She's blue. She's naked. She kills people. She doesn't talk much. She's a henchman, really — but what a henchman! As played by the eternally underrated Rebecca Romijn in the first three X movies, the character became one of the most iconic parts of the big screen mutant franchise. The rebooted X franchise has given Mystique more backstory, more dialogue, and an Oscar-winning actress, but Romjin gave Mystique, well, her mystique.
7 of 16
9. Ra's al Ghul, Batman Begins
Press materials for Christopher Nolan's reboot identified Liam Neeson as Henri Ducard, the man who trained young Bruce Wayne in the art of being Batman. And that's how Neeson introduced himself in the movie. But the final-act twist revealed he was actually supervillain Ra's al Ghul. Neeson ably knits together two very different comic book characters — he's a fine badass-with-a-heart-of-gold mentor, but once you know his true nature, you can also spot the messiah-complex warning signs. And his role in Begins helped bridge the gap between Neeson's period as a Serious Actor and his Taken-spurred career as Serious Badass.
8 of 16
8. Alexander Pierce, Captain America: The Winter Soldier
Like Neeson in Batman Begins, Robert Redford's turn in the Captain America sequel marks a savvy bit of adaptation-as-radical-alteration. Pierce in the comics is a longtime Nick Fury ally. As played by Redford onscreen, he's also a longtime Nick Fury ally...who turns out to be an agent of HYDRA. Redford's low-key performance makes for a nice contrast with the usual tendency toward cartoon villains. He's a company man, a bureaucrat from the David Simon school. Because the real supervillain is society, man!
9 of 16
7. Gabriel, Constantine
Yes, Tilda Swinton's only in the movie for a few scenes. And yes, her Gabriel doesn't have much to do with the version of the character who appeared in Hellblazer, much like how nothing in Constantine has anything to do with Hellblazer. But Swinton's turn is a classic of overdelivering, turning her half-breed angel into an androgynous lunatic with apocalypse on the mind. Just watch the scene where Swinton reveals her master plan. There's not a line or a facial expression wasted. The genius of Swinton in Constantine is how she proves that she could play every other supervillain on this list.
10 of 16
6. General Zod, Superman II
It's been over 30 years since Superman II. And you could argue that the curious art and careful science of adapting a comic-book villain to the big screen has been perfected. You can give the villain excessive backstory. You can provide costumes that look ''functional'' and ''gritty'' and ''not something you would wear to a retro-future Greco-Roman disco orgy.'' You can garnish them with impressive digital effects. You can do all this, and wind up with General Zod in Man of Steel, one of the most incoherent movie villains ever. Or you can just cast Terence Stamp and let him scream ''KNEEL BEFORE ZOD!''
11 of 16
5.5. ''The Mandarin,'' Iron Man 3
Not really a supervillain, and a minor outcry supposedly erupted over the Iron Man threequel's elaborate reworking of the Mandarin. I say ''supposedly'' because it's hard to imagine anyone really getting excited about the comic book character, who is problematic in all kinds of ways. And even if Iron Man 3 ultimately punted on the possibility of ever coming up with a really exciting villain for Iron Man, give the movie credit for coming up with a character who almost seems like a parody of the recent wave of self-serious supervillains. And give credit to Ben Kingsley, who's great as ''The Mandarin'' (complete with a ridiculous accent) and Trevor Slattery, the hilariously amoral man behind the curtain.
12 of 16
5. Sebastian Shaw, X-Men: First Class
Recent movie supervillains inevitably trend messianic. So there's something deliciously refreshing about Kevin Bacon's turn as Shaw, who radiates hedonistic joi de vivre even as he's plotting global domination. It helps that Bacon gets a fantastic introduction (speaking German, gleefully ruining poor little Magneto's life) and a great single-movie arc, complete with one of the nastiest exits for any comic book movie Big Bad ever. Fun fact: Bacon has said that he based his performance variously on Ted Turner, Hugh Hefner, and Donald Trump.
13 of 16
4. Magneto, X-Men franchise
Then again, there's nothing wrong with trending messianic, as long as you've got the authority to back it up. And in one of the two great blockbuster roles that defined his later career, Ian McKellen is all authority. As the proud, aggressive mutant opposite number to Patrick Stewart's pacifistic Professor X, McKellen's Magneto gave the first X trilogy an essential undercurrent of righteous rage.
14 of 16
3. Loki, Thor and The Avengers franchises
The joy of Loki is that he's been a different character in all three of his big-screen outings. In the first Thor, he's the younger brother struggling for attention who experiences a legitimate identity crisis: A passionately misguided soul. In The Avengers, he's not struggling anymore: Tasked with conquering the Earth for his new master, he swaggers through the movie like a King claiming his birthright. The Dark World is the closest Tom Hiddleston's Loki has come to his comic-book incarnation, a trickster god with fluid alliances. Given that movie's cliffhanger, it's fair to say that the best of Loki is yet to come.
15 of 16
2. Catwoman, Batman Returns
Tim Burton's second Batman movie is the rare superhero film where a villain pile-up works — Danny DeVito's Penguin almost made this list, and Christopher Walken's original-for-the-movie Max Shreck is terrifying/terrifying funny in his own right. But the movie belongs to Michelle Pfeiffer, who gives one of the great off-the-hinge performances as Selina Kyle, frump-turned-dominatrix. Pfeiffer's Catwoman is a vision of majestic slink. And the gonzo Selina/Bruce chemistry gives the movie a special frisson — ''Does this mean we have to start fighting?'' — that remains unique in superhero cinema.
16 of 16
1. The Joker, The Dark Knight
The only performance on this list to win an Oscar, and a monument to a gone-too-soon talent, Heath Ledger's Joker looms large over the history of superhero movies. And he looms over his own film. In stark contrast to the one-on-one personality conflict which motivated the Joker-Batman feud in the Tim Burton film, The Dark Knight is an urban epic, replete with mobsters and the moral descent of Harvey Dent and even a cameo by the Scarecrow. But it's Ledger's Joker who begins the movie, and it's the Joker who haunts every corner of the film. Not to mention the fact that essentially everything the Joker says is quotable, or that essentially every scene is a T-shirt ready meme. The Joker in the interrogation room. The Joker burning the money mountain. The Joker, in a nurse's outfit, basking in the hedonistic glee of blowing the world to Hell. And finally, the Joker swinging upside down, laughing into eternity.