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Top 20 Darkest Supervillain Portrayals

Top 20 Darkest Supervillain Portrayals
VOICE OVER: Andrew Tejada
These supervllains are downright chilling! For this list, we'll be looking at the most sinister and unsettling comic book antagonists that have ever been brought to live-action. Since we'll be talking about their villainous deeds, beware of spoilers ahead. Our countdown includes villainous portrayals of Lex Luthor, Ozymandias, Thanos and more! Which of these performances made your skin crawl the most? Let us know in the comments below.

Welcome to WatchMojo, and today we’re counting down our picks for the Top 20 Darkest Supervillain Portrayals. For this list, we’ll be looking at the most sinister and unsettling comic book antagonists that have ever been brought to live-action. Animated portrayals will be saved for another list. Since we’ll be talking about their villainous deeds, beware of spoilers ahead. Which of these performances made your skin crawl the most? Let us know in the comments below.

#20: Paul Dano as Edward Nashton [AKA The Riddler]

“The Batman” (2022)

When this film begins, we see The Riddler stalk and slaughter a man who’s at home with his family. All the while, Paul Dano adds the disturbing sounds of heavy breathing. Things only get darker from there. The Riddler makes targets suffer with traps that feel like they were ripped out of a “Saw” film. Although he does most of his dark deeds from a distance, he’s creepier up close. Paul Dano expertly conveys how The Riddler’s anger at corrupt people have driven the character into a dark hole. His detached performance makes it feel like the villain has no value for human life. By the time he’s captured, we’re certain Dano’s Riddler’s prouder of his evil acts than ever.

#19: Dane DeHaan as Harry Osborn [AKA the Green Goblin]

“The Amazing Spider-Man 2” (2014)

While reactions to the second Garfield outing were mixed, Peter Parker’s friend turned enemy delivers a creepy and sinister performance. DeHaan masterfully portrays the transition from a sweet friend of Peter’s to the insane Green Goblin. He teeters the brink of insanity for much of the film. This darker portrayal of Spider-Man’s archnemesis comes to a head in the final confrontation of the film, where DeHaan’s unsettling madness steals the show. Harry Osborn is uncomfortable to watch in this film because of his unhinged personality. DeHaan’s ease in portraying the darker side of a well-known character is captivating.

#18: Iain De Caestecker as The Doctor

“Agents of S.H.I.E.L.D.” (2013-20)

The charming Iain De Caestecker shocked everyone when he took a turn as a truly despicable villain. Although the actor normally played the kind and quirky Fitz, he also spent time playing an evil version of the character that was called the Doctor. De Caestecker removed every trace of warmth from his persona to play an unbelievably cold scientist. The Doctor he brought to life inflicted massive amounts of pain without blinking an eye. While he never took pleasure in his cruelty, he didn’t mind making someone suffer if it benefited him. Iain De Caestecker’s frightening work made us wary each time the Doctor showed up for another horrible appointment.

#17: Michael Shannon as General Zod

“Man of Steel” (2013)

Driven and determined, the villainous Kryptonian has come to Earth with a dark purpose; to terraform the entire planet to be a New Krypton. Shannon’s portrayal of the character is powerful and raw, and manages to appear almost regal and sympathetic as he explains his plans to destroy humanity to rebuild his home. Shannon’s Zod uses fear and mystery to intimidate the people of Earth. And he’s absolutely merciless in everything he does. From his monologues to his callous attitude towards humans, it’s clear that earth is just a means to an end. Michael Shannon turns Zod into a savage character who is feared and leaves a huge impression on movie-goers.

#16: Daniel Brühl as Helmut Zemo

The Marvel Cinematic Universe (2008-)

While not a physical threat to any of the Avengers, this was the first villain that succeeded in destroying the unity of the super-hero team. After his family was killed in the confrontation between Ultron and the Avengers, Zemo resolved to destroy the Avengers, no matter the cost. What makes Brühl’s performance grim is the subtle determination to kill innocents and ruin lives in order to achieve vengeance for his dead family. He also gives off the sense that he’d rather fail in darkness than live in the light. By bringing a more realistic take on the character to the screen, Brühl succeeds in making Zemo a dark and multi-dimensional villain.

#15: Michael Cudlitz as Lex Luthor

“Superman & Lois” (2021-)

It only took a couple of episodes of screentime to establish that this take on Lex was one of the most horrific we’ve ever seen. Michael Cudlitz ensures that the supervillain comes off as unnervingly still and composed while committing the most heinous crimes imaginable. So whenever he loses his composure, we’re filled with fear at what he’ll do next. The Cudlitz Luthor also projects a feeling of absolute dominance no matter where he goes. Whether he’s staring down an inmate or superpowered individual, it feels like he’s completely in charge. We would never want to get on the bad side of this Lex. There’s no telling what horrendous things he’s planning for us behind his calm composure.

#14: Michael Fassbender as Erik Lehnsherr [AKA Magneto]

Various Films

While this character has been portrayed excellently before, particularly with the terrific performance of Ian McKellen. But Fassbender’s take on the character brought Magneto to incredibly dark places. While given a sympathetic look at the origins of Magneto, Michael Fassbender still succeeds in showing the twisted side to the mutant’s quest for revenge. He has a calm look in his eyes as he murders those who stand in his way. There’s also the fact that he served an ancient mutant with plans to remake the world by destroying what existed before. Despite our sympathy for Magento’s origins, Fassbender's fierce performance demonstrates that the character lost a lot of light during his quest for revenge.

#13: Josh Segarra as Adrian Chase [AKA Prometheus]

“Arrow” (2012-2020)

Before Segarra’s Adrian Chase was revealed as a villain, he came off as being very passionate about stopping criminals. The actor brilliantly transformed that passion into intensity when he fully embraced his wicked persona. Segarra could effortlessly go from being charming to ruthless on a dime. However, the most unsettling part of his performance was that he fully convinced us that Chase thought what he was doing was 100% justified. During the series, the villain deceives innocent people, viciously torments heroes and even slays his own wife. But Segarra ensures that any hints of regret are quickly obscured under a blank or even content face. His Adrian Chase is totally committed to his twisted mission.

#12: Navid Negahban, Aubrey Plaza & More as Amahl Farouk [AKA Shadow King]

“Legion” (2017-19)

Since this parasitic villain took many forms, multiple actors deserve the credit for portraying him. No matter what body he’s in, he’s one of the most sadistic antagonists ever. Amahl Farouk was a demented telepath who lost his body and hid his consciousness in the mind of an infant named David. The villain spent years tormenting the boy as he grew up with haunting visions and horrifying entities. Negahban and Plaza both convince us that the Shadow King has no remorse for his misdeeds. Just a short list of his crimes include hijacking people’s bodies, imprisoning innocent minds and a whole lot of murder. Any actor who played the Shadow King only needed to remind us of their myriad of crimes to unsettle us.

#11: Chukwudi Iwuji as The High Evolutionary

“Guardians of the Galaxy Vol. 3” (2023)

Few characters have less disregard for life than Iwuji’s High Evolutionary. He doesn’t see any issues with slaying or mistreating any unfortunate creature that he experiments on. At certain points in the film, Iwuji’s emotionally detached performance greatly unsettles us. The amount of calm he has as he torments living beings is genuinely upsetting. Additionally, Iwuji can also abandon a sense of composure in an instant and lash out with self-righteous fury. The actor’s crooked and layered portrayal ensures that we're uncomfortable once he strolls onto the scene. Iwuji’s flawless acting made us afraid of the villain obsessed with perfection.

#10: Willem Dafoe as Norman Osborn [The Green Goblin]

Various Films

There are admittedly a few scenes where Dafoe brings a lot of campiness and fun to this dual villain role. But when you look closer, you’ll find a tremendously dark performance. While Dafoe’s Norman gets angry, he does still care for his loved ones. But his Green Goblin persona is built on the darkest and most violent impulses imaginable. In this supervillain form, he’ll attack his dearest friends and make people watch their loved ones die. The contrast between both sides gets really scary whenever the Goblin forcefully takes over the body he shares with Norman. Every time Dafoe’s mouth twists into the supervillain’s smile, we’re instantly filled with dread at what’s to come.

#9: Matthew Goode as Adrian Veidt [AKA Ozymandias]

“Watchmen” (2009)

In a unique turn of events, moviegoers had to wait until the third act to see how morally bankrupt this antagonist truly is. Goode’s Adrian Vedit seems like a run-of-the-mill conceited businessman at first. But in the final act, we discover that he’s been behind a long and twisted scheme to frame a superhero for the murder of millions of people. Goode reveals Adrian’s unthinkable plot with a matter of fact tone that makes it clear those lives meant nothing to him. Eventually, his calm turns to pride for his genocidal scheme. While Adrian’s true darkness is only apparent for a small fraction of the story, the sheer cruelty of his true nature made a big impact.

#8: Cameron Monaghan as Jerome & Jeremiah Valeska

“Gotham” (2014-19)

If you want two disturbing Joker performances for the price of one, then Cameron Monaghan has you covered. He initially plays a prototype version of the Clown named Jerome that is extremely manic and violent. The way the character revels at the sight of people in pain made our skin crawl. After Jerome dies, his twin brother Jeremiah becomes a different kind of prototype Joker. This time around, Monaghan makes this early edition of the clown into a cold and cruel villain who relies on his incredible intelligence to hurt others. He makes matters worse by constantly insisting that he’s sane. No matter whether you find Jerome or Jeremiah creepier, there’s no denying that both clowns are seriously demented.

#7: Josh Brolin as Thanos

“Avengers Endgame” (2019)

Although the mad titan makes multiple appearances in the MCU, the darkest portrayal of the character comes after the “Avengers Endgame” time skip. This Thanos comes off as a warmongering conqueror who is fully focused on reducing the universe’s population. While Brolin gave his titan a bit of vulnerability in the past, that’s completely absent here. The actor makes sure that this iteration of Thanos feels more dangerous than ever. Brolin only sounds happy when he’s given the chance to spread more death. It was truly impressive that the actor convinced us that a character who snapped away half of existence could get even worse.

#6: Teddy Sears as Zoom

“The Flash” (2014-)

Tom Cavanagh deserves a lot of credit for his unsettling performance as the Reverse Flash. However, Zoom was arguably the more terrifying villain. This twisted speedster served as a terrific foe for Barry Allen and his friends. Actor Teddy Sears initially pretended to be the heroic “Jay Garrick”. He played the role so well that nobody predicted that his kindness was a cover for a dark villain who delights in pain for pain’s sake. Meanwhile, the legendary Tony Todd sent chills down our spine by stepping in as the disguised voice of the evil speedster. Zoom’s only goal is to be the fastest man alive, and he isn’t afraid to kill or maim in order to get his way.

#5: Vincent D’Onofrio as Kingpin

“Daredevil” (2015-)

Nobody expected this performance to be as dark as it was. D’Onofrio manages to portray Wilson Fisk as a cold and calculating crime-boss. At the same time, he can also turn into a raging and psychotic man who will brutally decapitate a henchman for disappointing him. Kingpin’s vicious side is showcased beautifully by D’Onofrio. He can begin in a calm monologue before suddenly snapping and throttling someone to death with little effort. Whenever his Kingpin is present, it feels like the characters are sitting next to a walking bomb about to go off. D’Onofrio’s chilling performance makes it impossible to tell if he’s about to shake your hand or snap your neck.

#4: Danny DeVito as The Penguin

“Batman Returns” (1992)

Few actors can manage to be creepy, disgusting, horrifying and weird all at once, and still manage to put forward a compelling performance. DeVito’s Penguin is iconic because of how delightfully off kilter and dark he gets. He isn’t afraid to take risks and go over the top, and somehow finds a way to make the Penguin feared despite some of the silly lines. It should be near impossible to make a villain that considers himself to be more penguin than human seem dark and sinister. And yet, DeVito does a fantastic job of doing just that.

#3: Antony Starr as Homelander

“The Boys” (2019-)

When shady scientists were raising Homelander to be the most powerful hero the world had ever seen, they forgot to treat him with any love or affection. This detached upbringing eventually gave rise to an emotionally stunted, egotistical, and psychopathic villain. Antony Starr brings all those terrifying characteristics to every scene. There are multiple occasions where he gets emotional while violently executing an enemy. At the same time, there are even more examples of moments where he murdered people just because they were beneath him. But Starr’s Homelander is most terrifying when he’s taking pleasure in psychologically tormenting others. The actor never lets us forget that the man who was supposed to be the world’s greatest hero is actually its most dangerous villain.

#2: David Tennant as Kilgrave

“Jessica Jones” (2015-)

Imagine the twisted things you could do with powers of mind control, and then watch as Marvel one-ups you. Tennant’s portrayal of the sadistic Purple Man is unsettling to watch, but incredibly compelling. Tennant calmly narrates in a matter-of-fact tone what he wants his victims to do before they carry out his orders. Beyond his extravagant murders, however, it is Tennant’s sinister and casual way in which he longs for Jessica that truly makes his portrayal of the character masterful. Kilgrave is certainly the darkest villain in the Marvel Netflix universe, and that is all thanks to this brilliant performance.

#1: Heath Ledger as The Joker

“The Dark Knight” (2008)

The clown has been played on the big screen by several great actors. While Jack Nicholson gave an intimidating performance, Joaquin Phoenix gave us a tormented clown. But the menacing Joker that had a bit of everything with a few majorly dark surprises was Heath Ledger. His clown’s grim sense of humor meant he laughed through unsettling makeup at the bleakest events. And since Ledger’s Joker was prone to sudden mood swings, he could go from giggling to quiet and back to murderous within the span of minutes. Along the way, the clown caused the deaths of allies, foes and innocent people alike. His lack of a clear end goal also made it clear that Ledger’s clown would never stop casting a shadow over Gotham.

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