Written by Zack Hohenstein, E23 Digital Director

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“I firmly believe that a story is only as good as the villain.”  – Clive Barker

Everyone loves a hero. As audience members, we’re drawn to the charisma of an Iron Man. We’re inspired by Captain America’s leadership. Batman’s gothic presence is engrossing. I’m partial to Star-Lord’s sophomoric sense of humor myself.

But what purpose would these heroes serve without someone to oppose them?

A good villain can lift a pedestrian story to something remarkable. But what makes a good villain? I believe a memorable antagonist falls into at least one of three key groups:

  1. A villain that is incredibly evil
  2. A villain that is relatable, or has understandable motivations
  3. A villain that can make you laugh

No genre is more dependent on villains than the superhero genre. Twenty years ago, making a movie based on a comic book was viewed as a risky endeavor for studios. Multiple franchises and billions of dollars later, superheroes are a proven powerhouse of modern cinema. 

Yes, Martin Scorsese. I said cinema.

Dozens of blockbusters with iconic heroes in capes have integrated into pop culture. And in each of these movies there is someone standing in the protagonist’s way. This list is going to take a look at the best of these not-so-good guys.

Before we begin, I have to make a few things clear. 

I’m not going to use the phrase “bad guy” because oftentimes the “heroes” are pretty morally gray themselves these days. Sorry, Harley Quinn. You are not eligible for this list. To qualify for the list, an individual must have worked against the protagonist for at least one movie. Though, if the character has a redemptive arc throughout a series, that helps too. 

Another distinction to make is that this list ranks characters, not technically portrayals. So, that means a character can appear more than once if the character has been depicted in separate cinematic universes. Furthermore, the same character can be listed just once, even if portrayed by two different actors as long as it’s in the same timeline of films.

With all of that being said, let’s get started with some honorable mentions.

Honorable Mentions

– Prowler: Mahershala Ali (Spider-Man: Into the Spider-Verse)

– Penguin: Danny DeVito (Batman Returns)

– The Phantasm: Dana Delany/Stacy Keach (Batman: Mask of the Phantasm)

– Ozymandias: Thomas Goode (Watchmen)

– Deacon Frost: Stephen Dorff (Blade)

– Harvey Dent/Two-Face: Aaron Eckhart (The Dark Knight)

 

And now on to the real deal…

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25. Lex Luthor – Gene Hackman

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First Appearance: “Superman” (1978)

Iconic Quote:

Superman: Is that how a warped brain like yours gets its kicks? By planning the death of innocent people?

Lex: No, by causing the deaths of innocent people.

With the right mix of confidence, wittiness and indifference toward human life, Gene Hackman’s Lex Luthor earns your attention in any scene he’s in. His plan to sink the west coast into the ocean to boost the value of his adjacent property is gloriously campy in the best way. Though Hackman is less involved in the sequels, he is one of the most important villains in the history of the genre. Richard Donner’s “Superman” has stood the test of time, thanks in large part to Christopher Reeve’s titular hero and Hackman’s absorbing Lex Luthor.

24. The Riddler – Jim Carrey

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First Appearance: “Batman Forever” (1995)

Iconic Quote:

For if knowledge is power, then a god am I… Was that over the top? I can never tell.

Casting Jim Carrey as the Riddler was a stroke of genius in this sort-of-sequel to Tim Burton’s far superior Batman films. With his legendary comedic talents on full display, Carrey is the highlight in an otherwise unremarkable comic book movie. It’s like someone dialed his most zany impulses up by 50 degrees. No amount of costume changes or distinctly insane hairstyles can keep up with his chaotic energy.

23. Max Shreck – Christopher Walken

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First Appearance: “Batman Returns” (1992)

Iconic Quote: 

Selina Kyle: Okay, go ahead. Intimidate me, bully me if it makes you feel big. I mean it’s not like you can just kill me.

Shreck: Actually, it’s a lot like that.

Picture a typical, selfish business mogul who lacks a moral compass and disregards the common man. Now add a Christopher Walken voice and a willingness to murder to protect his brand. That’s Max Shreck. Having never appeared in any previous comic, he was a completely original antagonist for Tim Burton’s first and only Batman sequel. Less over the top evil and more corporate coldness; Shreck is a grounded villain in a series full of outlandish rogues.

22. Helmut Zemo – Daniel Brühl

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First Appearance: “Captain America: Civil War”

Iconic Quote:

Steve Rogers: Who are you? What do you want?

Zemo: To see an empire fall.

The third film in the Captain America series is essentially an Avengers movie in everything but name. Where ultra-powerful forces such as Loki and Ultron failed in bringing down Earth’s Mightiest Heroes, a mere mortal man succeeded. Helmut Zemo manipulates and murders to execute his plan to divide Cap and Iron Man. Completing a promise he made in a tragic backstory, Zemo is one of the few villains to complete his mission.

21. William Stryker – Brian Cox/Danny Huston/Josh Helman

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First Appearance: “X2: X-Men United” (2003)

Iconic Quote:

Don’t lecture me about war. This already is a war.

Though Danny Huston and Josh Helman appear as younger versions of William Stryker in subsequent films, it’s Brian Cox’s portrayal in “X2: X-Men United” that secures the spot on this list. Stemming from the death of his wife at the hands of his own mutant son, his plan to kill every mutant on the planet is properly motivated and suitably extreme. He’s also the one who gave Wolverine his iconic adamantium claws.

20. The Winter Soldier – Sebastian Stan

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First Appearance: “Captain America: The Winter Soldier” (2014)

Iconic Quote:

Steve Rogers: I’m not going to fight you. You’re my friend.

Bucky: You’re my mission.

A man of few words, Bucky Barnes’ brainwashed alter-ego is a deadly assassin that lets his skills do the talking. Sure, he eventually snaps out of his mental mishaps with some help from his old friend Steve Rogers. But before that, this guy was terrifying. He also looked pretty cool with a metal arm, a scary mask and some beautiful black locks. Plus this fight scene underneath the highway is one of the best action sequences in the entire MCU. 

19. Mr. Glass – Samuel L. Jackson

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First Appearance: “Unbreakable” (2000)

Iconic Quote:

It’s alright to be afraid, David, because this part won’t be like a comic book. Real life doesn’t fit into little boxes that were drawn for it.

A comic store owner with glass bones is obsessed with finding a real superhero. The only catch is he has to become a supervillain to do it. Orchestrating devastating “accidents” and murdering hundreds just to find someone who can survive it is pretty extreme but Mr. Glass isn’t supposed to be the most rational. He’s just really, really smart. 

Samuel L. Jackson’s committed performance paints Mr. Glass as a sympathetic figure until the final twist reveals just how twisted he is. He wanted to be David Dunn’s friend until he finally embraced his true identity: his nemesis.

18. Syndrome – Jason Lee

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First Appearance: “The Incredibles” (2004)

Iconic Quote:

Everyone can be super! And when everyone’s super… no one will be.

Syndrome just wanted to be a superhero. So did I, as a child. I’m sure many others did too. So, when Mr. Incredible rejected him and set him on a path of villainy, an entire generation of kids felt the rejection with him. A completely self-made man in a world of heroes who are born with their abilities, Syndrome is eccentric and impressive, even if a bit sadistic. Add in some fun vocal work from Jason Lee and you’ve got yourself an awesome animated antagonist.

17. Vulture – Michael Keaton

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First Appearance: “Spider-Man: Homecoming” (2017)

Iconic Quote:

So don’t mess with me. Don’t interfere in my business again. Because I will kill you and anyone you care about.

A working class villain is something to be. Michael Keaton’s Vulture isn’t out to destroy the planet. He doesn’t want world domination. He just wants to make a good living for his family after being run out of business by Stark Industries. His identity as a family man gives the character a good human element. It’s this quality that makes the moment when he’s willing to murder a teenage boy with a huge pile of concrete all the more brutal.

16. Ultron – James Spader

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First Appearance: “Avengers: Age of Ultron” (2015)

Iconic Quote:

There are no strings on me.

Ultron’s introduction is as intimidating as it is unsettling. He wakes himself into sentience, educates himself on the history of the world, “kills” Jarvis and proceeds to interrupt the Avengers’ party, calling them all puppets. His ability to travel through the internet and rebuild himself into different metal legionnaires makes him a substantial threat. 

James Spader’s icy voice work is suitably chilling as well. Recognizing the Avengers as a destructive force in the world, despite their best intentions, makes Ultron an antagonist that forces the heroes to examine their own actions and their consequences.

15. Joker – Mark Hamill

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First Appearance: “Batman: Mask of the Phantasm”

Iconic Quote:

That’s it. That’s what I want to see, a nice big smile.

Hearing Mark Hamill’s Joker laugh will make you forget that the man was ever Luke Skywalker. His vocal portrayal of the Clown Prince of Crime is zany and psychotic in all of the most fun ways. More comical without sacrificing any homicidal tendencies, the Joker arrives late in “Batman: Mask of the Phantasm” but makes the most of every minute of screen time he’s given. Even in the face of what seems to be his impending death, he lets out one last laugh as the world explodes around him.

14. Mysterio – Jake Gyllenhaal

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First Appearance: “Spider-Man: Far From Home” (2019)

Iconic Quote:

These days, you can be the smartest guy in the room, the most qualified, and no one cares. Unless you’re flying around with a cape, or shooting lasers with your hands, no one will even listen. Well, I’ve got a cape and lasers.

This guy knows how to trick people. Hell, his mere presence in this Spider-Man sequel tricked me into thinking a multiverse was being introduced. A classic character from the webslinger’s deep rogue gallery, Mysterio lives up to his name in 2019’s “Spider-Man: Far From Home” with some psychedelic and haunting illusions. The guy even whipped out a zombie version of Iron Man to mess with Peter.

Jake Gyllenhaal is charismatic in the role, giving the character just a touch of decency under his mad drive for success. However, his ultimate moment comes after – spoiler – his death when he reveals to the world the true identity of Spider-Man.

13. Black Mask – Ewan McGregor

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First Appearance: “Birds of Prey: And the Fantabulous Emancipation of One Harley Quinn” (2020)

Iconic Quote:

You’re a fucking moron.

Ewan McGregor’s Black Mask is easily the funniest comic book villain I’ve ever seen. His eccentric personality and charisma steal any scene he’s in. He also has a taste for watching his “BFF” Victor Zsasz peel off the faces of those who cross him. There isn’t much depth to him but the sheer level of entertainment he provides in every moment he’s present makes him one of the most enjoyable villains in the history of the genre.

12. Ra’s Al Ghul – Liam Neeson

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First Appearance: “Batman Begins” (2005)

Iconic Quote:

If someone stands in the way of true justice, you simply walk up behind them and stab them in the heart.

Ra’s Al Ghul and his League of Shadows just want to rid the world of crime. The only problem is they want to kill a lot of people to do it. A man of principle but also one of harsh absolutism, Ra’s is a comic book villain who believes in something. He has no ego in his quest, but is instead driven by a sense of duty to the world.

He teaches Bruce Wayne to be something more than a man and even develops a friendship with him along the way. That’s why it hurt him when they were forced to become enemies. Liam Neeson’s portrayal is assuredly smooth and his backstory is only made more fascinating in “The Dark Knight Rises”. 

11. Killmonger – Michael B. Jordan

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First Appearance: “Black Panther” (2018)

Iconic Quote:

Just bury me in the ocean with my ancestors who jumped from ships, ’cause they knew death was better than bondage.

Abandoned in a harsh environment and raised to fight, Michael B. Jordan’s Killmonger is the perfect foil to T’Challa in “Black Panther”. Whereas the hero was born into royalty in a country with an abundance of resources, he was forced to fend for himself and try to forge his own path to power. Addressing important racial injustice themes, Killmonger fights his way back to the throne of his ancestral home. 

Jordan’s performance sells the pain and anger in a way that inspires sympathy. Even though his plan failed in the end, his quest to help those who needed it was achieved when T’Challa decided to share Wakanda’s resources with the world. When the villain significantly changes the hero for the better, that is an effective antagonist. 

10. General Zod – Michael Shannon

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First Appearance: “Man of Steel” (2013)

Iconic Quote:

You believe you son is safe… I will find him. I will find him, Lara. I WILL FIND HIM!

Born with the sole purpose to defend Krypton, General Zod acts to save his race from extinction. When he’s prevented from doing so by Jor-El and later by his son, Superman, he’s reduced to a powerful man left powerless by the actions of a few. It’s his sense of duty that drives him. When that duty is taken away, all he has left is rage. 

What sets Zod apart is his guilt over the things he’s done and the things he has to do. He doesn’t thirst for violence. But he does it in the name of protecting his people. That is why when his people are all gone, he snaps. Michael Shannon captures the pain and fury and makes it feel genuine when it’s finally unleashed.

9. Dr. Octopus – Alfred Molina

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First Appearance: “Spider-Man 2” (2005)

Iconic Quote:

I will not die a monster.

Another tragic figure, Dr. Octavius made a costly miscalculation and accidentally killed his wife because of it. Fueled by grief and manipulated by four A.I. metal arms, he sets off to rebuild his machine so her death will not be for nothing. He’s sympathetic but also intimidating. If you don’t believe me then watch this scene where doctors try to take the arms off of him.

The strength of his character comes from his arc. After realizing what he’s become, he takes back charge from the metal arms and redeems himself. 

8. Green Goblin – Willem DaFoe

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First Appearance: “Spider-Man” (2002)

Iconic Quote:

Had you not been so selfish, your little girlfriend’s death would have been quick and painless, but now that you’ve really pissed me off, I’m gonna finish her nice and slow. MJ and I are going to have a hell of a time.

Willem DaFoe gets to be a murderous mad scientist with a scary goblin mask and grenades that turn people into skeletons. I don’t know about you but that sounds pretty awesome to me. The Green Goblin more than any other villain on this list can be scary. This is thanks in large part to the directorial instincts of Sam Raimi.

Whether he’s in costume or not, Norman Osborn is anxiety-inducing. If forcing a hero to choose between saving the love of his life or a cable car full of children isn’t classic villain behavior then I don’t know what is. 

7. Loki – Tom Hiddleston

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First Appearance: “Thor” (2011)

Iconic Quote:

Nick Fury: We have no quarrel with your people.

Loki: An ant has no quarrel with a boot.

The God of Mischief lives up to his name. Having appeared in six films to this point, Loki has seemingly died twice, tried to commit genocide, brainwashed Hawkeye, tried to take control of earth, impersonated his father for the throne and escaped into the unknown with the Tesseract. Now we don’t truly know where he is. What we do know is that Tom Hiddleston’s performance in the role is the right mix of charisma and murderous angst to keep us interested.

His desire of approval from his father Odin gives him some emotional stakes to go along with his persistent plotting. Lied to about his true heritage and consistently in his brother’s shadow, Loki suffers from some serious identity crisis. However, his redemptive moments allow him to have an arc that feels both earned and satisfying.

6. Catwoman – Michelle Pfeiffer

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First Appearance: “Batman Returns” (1992)

Iconic Quote:

I am Catwoman. Hear me roar.

After being tossed out of the highest window in the tallest tower, Selina Kyle is given nine more lives to exact her revenge on her boss. Her transformation from a timid and clumsy secretary to an audacious criminal is believable and suitably quirky for a Burton Batman film. Michelle Pfeiffer sells both the identities of Selina Kyle and Catwoman, letting the anger that drives her reach the surface only a few times from under her dark sense of humor. Having an awesome costume like that doesn’t hurt either.

5. Bane – Tom Hardy

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First Appearance: “The Dark Knight Rises” (2012)

Iconic Quote:

Your punishment must be more severe… We will destroy Gotham and then, when it is done and Gotham is ashes, then you have my permission to die

This guy literally breaks Batman’s back. He picks his entire body up and brings it down on his knee. His bulky physique is intimidating and his plan to torture Bruce and destroy his city is appropriately merciless. And if you can recall all the way back to 2012 then you’ll remember just how quotable this guy was. In a role where his mouth is concealed the entire time, Tom Hardy turns in a performance with a reliance on the expressiveness in his eyes. That might sound stupid but it works. And who doesn’t love to impersonate the Bane voice?

4. Joker – Jack Nicholson

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First Appearance: “Batman” (1989)

Iconic Quote:

Joker: “Tell me something, my friend. You ever dance with the devil in the pale moonlight?”

Bruce Wayne: “What?”

Joker: “I always ask that of all my prey. I just… like the sound of it.”

The superhero genre owes a lot to Tim Burton’s “Batman”, which proved that superheroes could be serious, marketable blockbuster properties. And without Jack Nicholson’s Joker, it might not have been the success it was. With no clear motive except to kill people and have fun doing it, this rendition of the iconic villain is the perfect foil to Michael Keaton’s Batman. Where the hero is quiet, brooding and serious, the Joker is loud, eccentric and animated.

Nicholson is good at playing people who have gone off the deep end (see “The Shining”) and this is no exception. The 3-time Oscar winner knows he’s in a comic book movie and plays the role accordingly, chewing scenery and being ridiculous as possible. 

3. Magneto – Ian McKellen/Michael Fassbender

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First Appearance: “X-Men” (2000)

Iconic Quote:

You know this plastic prison of theirs won’t hold me forever. The war is still coming, Charles. And I intend to fight it, by any means necessary.

Magneto can move metal. That’s his mutation. As you could assume, this ability has a lot of applications when it comes to fighting humans and other mutants alike. He’s primarily been a villain, albeit one with various heroic moments along the way.

Magneto is a Holocaust survivor. He’s seen what horrors mankind is capable of. This past is what drives him to protect his fellow mutants, with violence being the only definite way to do that in his eyes. He’s fought for himself, his friends and his family and lost many times. He’s endured hardship after hardship throughout the sprawling X-Men series.

Portrayed by two incredibly talented actors at different points in his life, we have seen every conceivable side of this man. The depths and heights they’ve explored with the character make him a defining piece of the entire superhero genre. And if you don’t get amped when you hear the Magneto music from “X-Men: First Class” then you need to take another good look at your opinions.

2. Joker – Heath Ledger

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First Appearance: “The Dark Knight” (2008)

Iconic Quote:

Why so serious?

Has any character besides Heath Ledger’s Joker ingrained himself into pop culture with only one movie appearance? An agent of chaos, this rendition of the most famous comic book villain in history just wants to watch the world burn. Like Batman, he is a symbol and therefore he cannot be destroyed or bought out. He cannot be threatened. The interrogation scene between Batman and the Joker epitomizes this idea.

 

His actions force the “civilized people” to question their morals. He forces Batman to consider breaking his one rule that separates him from any other criminal. He succeeds in bringing down Gotham’s “White Knight” Harvey Dent, not by killing him but by bringing him down to his level of lawlessness. The Joker represents the escalation that Jim Gordon warned Batman about.

Vigilante justice can be met with vigilante injustice.

To bring him down, Batman had to bring himself down with him. And all of it is so engrossing because of the dedication that Ledger gave to the role, one that earned a posthumous Oscar at the 2009 Academy Awards.

1. Thanos – Josh Brolin

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First Appearance: “The Avengers” (2012)

Iconic Quote:

Dread it. Run from it. Destiny arrives all the same. And now it’s here. Or should I say, I am.

Driven by a personal sense of destiny to save the universe from itself, Josh Brolin’s Thanos wouldn’t consider himself a villain, though he wouldn’t care if he was called one either. The aura he generates is one of superiority, but not one of condescendence but similar to how a father would view a child who simply did not understand.

Built up as the ultimate threat through teases in previous films, Thanos did not disappoint when he arrived as the central antagonist in “Avengers: Infinity War”. He killed almost an entire ship of Asgardians, knocked Hulk out, killed Heimdall and Loki before leaving Thor to die. This all occurs before the title of the movie even appears on screen.

The most surprising aspect of Thanos’ portrayal is the emotional depth he is given. His relationship with his daughter Gamora gives him a human feel that’s lacking in other powerful villains of the genre. It’s clear that he loves her, which makes it all the more gut-wrenching when he sacrifices her to achieve his destiny. But even when he finally succeeds, her death still haunts him. He destroys the stones to avoid temptation and willingly accepts his fate at the hands of the Avengers. 

Also – his arrival in Wakanda might’ve been the coolest scene in the MCU up to that point.

 

“Avengers: Infinity War” and “Avengers: Endgame” would not have had the same impact if the threat was underwhelming. Thanos commands a sense of fear and respect. The various fights between different Avengers and the Mad Titan rank among the best in the entire genre. Almost every line of his dialogue is quotable. Serving as the primary antagonist of two of the most profitable films of all time, his presence at the top spot was unavoidable. 

He is inevitable.

 

Thank you for reading.

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