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VOICE OVER: Patrick Mealey WRITTEN BY: Cristina Otero
We all have a dark side, right? Welcome to WatchMojo, and today we're counting down our picks for the most charming, compelling film villains we can't bring ourselves to hate—animated ones not included, unfortunately. Spoiler alert: Sympathetic villainy and some major plot points will ensue. Our countdown includes villains from movies “The Dark Knight”, “Blade Runner”, “Austin Powers” and more!
Welcome to WatchMojo, and today we’re counting down our picks for the most charming, compelling film villains we can’t bring ourselves to hate—animated ones not included, unfortunately. Spoiler alert: Sympathetic villainy and some major plot points will ensue. Which other movie villain had you feeling sympathy for the devil? Let us know in the comments down below!

#20: Captain Hector Barbossa

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“Pirates of the Caribbean” franchise (2003-) Some of our most beloved bad guys keep us on our toes, and that fits Hector Barbossa to a T. Introduced as a straightforward villain in “Curse of the Black Pearl,” Barbossa became a tenuous ally to Captain Sparrow—though after getting resurrected from the dead. Both intimidating and witty, Barbossa is every inch the charming, roguish pirate with a flexible moral compass. More than that, he undergoes character development throughout the series, forming bonds and repartee with Sparrow, Elizabeth, and the crew. This character arc culminates in the pirate's final and poignant sacrifice to save his daughter. Honestly, what’s not to like?

#19: Jacobim Mugatu

“Zoolander” (2001) & “Zoolander 2” (2016) Some villains have the power of style and pithy one-liners. Jacobim Mugatu may be a criminal, but one law you won’t see him breaking is the law of good taste. Even if he has to brainwash people to kill a progressive prime minister to prevent him from eliminating those cheap sweatshops. Mugatu may be a shameless capitalist exploiter of child labor. But on the other hand, he brainwashes people into assassination with “Relax” by Frankie Goes to Hollywood. This walking satire of the fashion industry has got groove and charisma all of his own. So really, we got to stan.

#18: Castor Troy

“Face/Off” (1997) Now this is a fun villain part for both the audience and actors, plural. In this action thriller, both John Travolta and Nicolas Cage play Castor Troy, a name and personality straight out of Greek mythology. Sure enough, despite his unhinged actions, Castor’s devotion to his younger brother Pollux is touchingly sympathetic. Castor’s unhinged villainy—and random Handel’s “Messiah” hate—is memorable and undoubtedly one of the many best things about this cult action classic. His character is so iconic that Cage has even confirmed that he'd be willing to return to play Castor. Make it happen, Hollywood!

#17: Vincent

“Collateral” (2004) Sociopathic hitmen may be a dime a dozen, but few are as charismatic as Vincent, the hitman who takes humble cab driver Max hostage. Erudite, sophisticated, and seductive, Vincent is the modern-day devil to a terrified Max, threatening him to go along with his criminal endeavors and offering him a dark vision of ambition unfettered. While Max eventually breaks free from Vincent's thrall, the latter's charisma is the most noteworthy. Here Tom Cruise got a chance to go beyond his usual genetic heroics and deliver a subtle and challenging performance. It pays off handsomely with a villain we won’t forget anytime soon.

#16: Howard Payne

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“Speed” (1994) A retired bomb squad officer-turned-terrorist, Payne brings a world of pain to the protagonists of this action flick. Payne plants a bomb that is programmed to detonate if the bus goes below 50 miles per hour, and hero Jack Traven must stop him. Sounds generically villainy enough, right? Except Payne is played by the talented Dennis Hopper, transforming a standard villain into a scene-stealer. So it’s especially unfortunate that Payne’s end is anticlimactic, with Payne killed by a train light. What a painful end. At least we had fun with Payne while it lasted.

#15: Betelgeuse

“Beetlejuice” (1988) Villains are dangerous. Villains are deadly serious. Villains can even be tragic. But sometimes villains are just sleazy poltergeists who marry prepubescent children. When a deceased couple hires Betelgeuse to scare away the new family living in their house, they get more than they bargained for. They stop Betelgeuse from wreaking havoc and trying to marry the underaged Lydia, sending him back to bureaucratic hell. Still, Betelgeuse is so wacky and spontaneous we could stand to watch another hour or two of his ghostly antics–set, of course, to Harry Belafonte music.

#14: Cyrus “The Virus” Grissom

“Con Air” (1997) This film about a prison break onboard an aircraft features one of the most psychotic and interesting villains thus far: Cyrus "The Virus" Grissom. Amid the bombastic absurdity of this typically ‘90s action flick, Cyrus stands out as a criminal mastermind, with typically scenery-chewing aplomb. Cyrus manages to take over the plane, bounding the guards and disguising them as inmates. Although Cyrus and his two associates are eventually killed, it is due to Cyrus' own intelligence that they even got this far. Unbelievable in its action set pieces the film may be, but John Malkovich’s performance as this intellectual hijacker reminds us not to take the film too seriously.

#13: Vizzini

“The Princess Bride” (1987) It’s inconceivable that a list of lovable villains would not have one of the most memorable. Vizzini along with Fezzik are the bumbling kidnappers of Princess Buttercup and must contend with the pursuit of Dread Pirate Roberts. Vizzini’s intelligence may be highly overstated, but his brave attempts at logic and words with more than two syllables have endeared him to audiences. And in the case of the poisoned cups, his trust in his own intelligence is nothing less than hilarity. You almost feel sorry for his quick exit from the story; he could have at least gotten into more inconceivable situations.

#12: Douglas Powers a.k.a. Dr. Evil

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“Austin Powers” franchise (1997-) With a villain name like that, one would expect a fun, memorable villain. Conceived as a parody of James Bond villains, Dr. Evil is likewise fun and funny to watch. With his pinkie finger tic, increasingly ridiculous backstory, and over-the-top evil plans, Dr. Evil is less of a threat than simply pettiness. His being Austin Powers’ nemesis boils down to the latter becoming the International Man of Mystery and not him. Perhaps to be expected for the adoptee of a boulangerie owner and a French sex worker with webbed feet. At least he and Mini-Me have swag.

#11: Captain James Hook

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“Hook” (1991) Speaking of charming, roguish pirates. This cult film is undoubtedly bolstered by its villain. Dustin Hoffman makes for a fantastic Captain Hook and is one of the best versions of the character. Dramatic, unhinged, and utterly hilarious, Hoffman’s Hook is the perfect foil for Robin Williams’ grown-up Peter, even building a camaraderie with Peter’s son, Jack. Even in the face of defeat, Hook takes it all in stride and even dignity… until he whips out his dagger and tries to get Peter one last time. What, indeed, would the world be without Captain Hook in it?

#10: Severus Snape

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“Harry Potter” franchise (2001-11) Let’s hear it for the Half-Blood Prince! The most complex and morally gray character in all of “Harry Potter,” Severus Snape elicits strong reactions. Cold, resentful, and the favorite of the similarly complicated Draco Malfoy, Snape nevertheless has worked behind the scenes to ensure Harry’s and other’s safety. We later find out that Snape is indeed loyal to Dumbledore, even killing him on his orders and working against Voldemort. The reason? He does it out of his great love for Harry’s mother, Lily. With such poignant motivations, Snape is one of the rare antagonists that truly wins our sympathy.

#9: Francis “Frank” Costello

“The Departed” (2006) Now this mobster is not one you should ever cross. Jack Nicholson plays the Irish Frank Costello, one of the most vicious and sadistic of mob bosses in Boston. Being Irish Catholic at a time of great racism and discrimination obviously informs Costello’s law-unto-himself attitude. Costello even has a fatherly streak, acting as a sort of mentor and father figure to Billy Costigan. It turns out Costello’s character is based on a real-life gangster, who sold out his fellow criminals in order to climb the ranks. So Costello’s dark charisma is truly less than fiction.

#8: Roy Batty

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“Blade Runner” (1982) In a world where replicants are tracked down and killed, it’s not rocket science which characters will win the audience’s sympathy. A rogue replicant, Roy has been driven to desperate and questionable acts in evading the blade runners, including the film’s protagonist Deckard. In the climax, when Deckard is hanging from the roof, Roy even saves him, to the former’s shock. In the end, though, you can’t outrun death, either as a replicant or a human. As Roy’s replicant body loses life force, he delivers a poignant and unforgettable monologue. This android definitely dreams of electric sheep.

#7: O-Ren Ishii

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“Kill Bill: Volume 1” (2003) The Bride’s most iconic would-be killers, the Viper Assassination Squad, don’t lack for iconic characters. But O-Ren Ishii may be one of the most memorable. This Chinese-Japanese American assassin has had to work to ensure respect from her racist and sexist fellows. O-Ren took revenge after witnessing her mother and father’s deaths at the hands of the Yakuza crime syndicate, becoming one of the world's top assassins. Though the Bride crosses O-Ren off her list, one can easily see the similarities between the two characters, who worked so hard for their due in a world stacked against them.

#6: Hans Gruber

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“Die Hard” (1988) Another entry, another iconic Alan Rickman character. Hans is a German thief and criminal mastermind who holds Nakatomi Plaza for $640 million on Christmas Eve. Suave, sophisticated, and conniving, Hans has many iconic moments, from his taste in Beethoven to his jaunty machine-gun antics. He even acts the part of a hostage, on top of his role as a terrorist. Even his death scene is awe-inspiring, dramatically falling to his death from the tower. It’s no wonder that Gruber has become one of the most iconic villains in film history, played by one of the most talented character actors.

#5: Raoul Silva

“Skyfall” (2012) There have been many iconic James Bond villains throughout the years. But this former M16 agent-turned-terrorist may be the best of them. Silva’s turn towards villainy is understandable, having been left behind as a prisoner by M and tortured. Keen on vengeance, Silva embarks on an intricate plan to kill M, even capturing Bond in the process. Javier Bardem’s performance is magnetic, and the fact that he does manage to kill M cements him as one of the most chilling Bond villains in the canon. And like all villains, his being a mirror to Bond presents an alternate vision of what Bond could be.

#4: The Joker

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“The Dark Knight” (2008) One of the most famous psychopathic villains of all time, the Joker in all iterations is something to remember. But by far the most magnetic and menacing has to be Heath Ledger’s renowned Joker from Christopher Nolan’s “The Dark Knight.” Though initially controversial, Ledger’s Joker is now one of the most lauded, his reign of terror distinct and unique. In more than one bone-chilling monologue, he even gives a backstory of his grisly clown's grin, actually a facial scar. Amid all the comic-book jesters of other Batman media, Ledger's edgy Joker is one you’d better take seriously.

#3: Hannibal Lecter

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“The Silence of the Lamb” (1991) Now this is one guest you won’t want to invite for dinner. Serial killer Hannibal Lecter prefers his meals with human flesh, coupled with fava beans and a nice Chianti. But it’s his intellect and social graces that win us over as he helps Clarice capture Buffalo Bill, even developing a soft spot for the plucky novice agent. Refined, ultra-logical, and sophisticated, Lecter resembles more a murderous Sherlock Holmes than a brutal serial killer. A Sherlock Holmes who makes it a point to eat the rude, granted. But one that, like the iconic detective, is truly unforgettable.

#2: Harry Lyme & Marv Murchins

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“Home Alone” (1990) & “Home Alone 2: Lost in New York” (1992) There are fun villains. There are sympathetic villains. And then there are just villains who are so bad at their roles they wind up endearingly sympathetic instead. Marv and Harry are ordinary thieves with the unfortunate luck of targeting the house of a burgeoning child sociopath. Just kidding. But really, Kevin’s effective and increasingly dangerous traps would leave even hardened criminals at death’s door. Marv and Harry are simply two bumbling burglars too dumb to evade them. In the end, we wince more in sympathy than Schadenfreude at Marv and Harry’s many, many downfalls.

#1: Loki

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Marvel Cinematic Universe (2008-) There is nothing lowkey about Loki. Based loosely on his mythological counterpart, Loki quickly became one of the most beloved villains not only in the MCU, but of all time. Portrayed by Tom Hiddleston, Loki is a trickster god with some very relatable grievances: His (adopted) father Odin prefers his blonde himbo son, Thor, to the point of neglecting Loki. Still, despite Loki’s scheming and double-crossing, he and Thor share the typical brother relationship, full of jealousies and unexpected alliance. Couple all that with Hiddleston’s Shakespearean gravitas, and it’s no wonder Loki is such a fan favorite, enough to have garnered him his own TV series.

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