Villains can be much more fun to play than heroes. Just ask Gary Oldman or Christoph Waltz or any actor who’s built a résumé filthy with scoundrels. But perhaps the dark side exerts a particularly seductive pull on those performers who don’t specialize in heavies, those who have established a reputation for playing the virtuous, the trustworthy, even the merely goofball. Casting the most upstanding stars against type as big bads can be thrilling—for the star and the audience alike. Below, we’ve singled out 23 actors who pushed against their history or habit of playing good, either moving way outside their normal wheelhouses or putting a malevolent spin on their established personas. Note: We’ve excluded climactic twist reveals of villainy, because that would be a much, much longer list.


1. Albert Brooks, Drive (2011)

It’s the voice: purring and avuncular, eager to assure and be reassured. As a comedian, Albert Brooks used this tool to embody a series of insecure, good-natured sad sacks throughout the ’80s and ’90s, then applied it to warm up a slate of post-millennial animated films. And it’s that voice again that makes his turn in Drive, as the Jewish mobster Bernie Rose, so deeply troubling. It’s still Brooks up there, walking around in flowing, rich-guy silk shirts, but director Nicolas Winding Refn reveals his monstrous nature elliptically, with a penchant for violence that pops out as quick and neat as a switchblade. Apparently, to sell the director on the off-key casting, Brooks pinned Refn against the wall, then whispered, “To be violent, you don’t have to scream at people.” It’s this very mixture of gentleness and malevolence that leads to the movie’s most disturbing scene, when Brooks murders his accomplice and gently reassures him, as he bleeds out, “Don’t worry, don’t worry. That’s it. There’s no pain. It’s over.” He sounds like he’s whispering Nemo to sleep. [Clayton Purdom]


2. Henry Fonda, Once Upon A Time In The West (1968)

Henry Fonda’s image as a movie star was inextricably bound up with the American West, particularly its foundational values of laconic individualism and benevolent patriarchy. Described by his contemporary Richard Widmark as “the frontier American—part history, part folklore, part mythology,” he’d be an idealized father figure even if his daughter Jane hadn’t become a movie star as well. Leave it to one of the genre’s first great revisionists, Sergio Leone, to tap into the dark side of manifest destiny by casting Fonda as Frank, a merciless enforcer of corporate interests (in this case, a land-hungry railroad magnate) who slaughters an entire family in his first scene of Once Upon A Time In The West. Confronted with a terrified young boy standing amid the bodies of his dead father and siblings, one of the assembled men asks, “What are we going to do with this one, Frank?” After considering for a moment, Fonda coolly replies, “Now that you’ve called me by name…” and kills the boy on the spot. Sorry, kid. It’s just business. [Katie Rife]


3. Sarah Michelle Gellar, Cruel Intentions (1999)

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Sarah Michelle Gellar had been playing Buffy Summers for nearly three whole seasons before she threw her good-girl image to the wind with a teen-sex-romp makeover of Dangerous Liaisons. Trading her iconic blonde tresses for a raven-black ’do, Gellar stars as Kathryn Merteuil, sociopathic teenage royalty of a Manhattan prep school, manipulating the love lives of her classmates for perverse entertainment. While Kathryn disguises her, well, cruel intentions behind an angelic rich-kid reputation (“I’m the Marcia fucking Brady of the Upper East Side,” she quips), Cruel Intentions allowed Gellar to part ways with the more squeaky-clean, heroic persona she cultivated on television. Her aristocratic femme fatale grinds on her stepbrother (I Know What You Did Last Summer costar Ryan Phillippe), snorts coke out of a crucifix necklace, and locks lips with a virginal peer (Selma Blair). Ultimately, it’s all rather tame, but Gellar runs with this rare opportunity to commune with her dark side. It was also as close as Buffy fans would get to seeing the slayer go full vamp. [A.A. Dowd]


4. Tom Cruise, Collateral (2004)

Tom Cruise movies from the first decade or so of his megastar career tend to observe his character reckoning with how to best use some kind of preternatural skill—flying planes, driving cars, shooting pool, tending bar—to eventually redeem himself. In Michael Mann’s nocturnal thriller Collateral, the Cruise character has either never had that reckoning or long since dismissed it. For his first outright villainous role (Interview With The Vampire only half counts), Cruise plays Vincent, a contract killer whose special talent is murder. The movie came toward the end of a long run of Cruise toying with his golden-god image, and outfitting him with gray hair, a cold heart, and a familiar combination of superhuman running and bullshit-artist pep talks makes it as worthy a Cruise star study as a Mission: Impossible movie. The way Vincent talks to his unwilling sidekick, Max (Jamie Foxx), even sounds a bit like Hunt giving orders to IMF team members, reconfigured to raise questions about whether this confident, handsome man is trustworthy (something Cruise’s public would have to ask themselves in real life not long after). [Jesse Hassenger]


5. Angela Lansbury, The Manchurian Candidate (1962)

It’s only the aftermath of 30 years of singing teapots and neatly solved murders that makes Angela Lansbury’s Oscar-nominated villain turn in The Manchurian Candidate feel shocking or out of place. Before that, Lansbury was a fairly regular wearer of the black hat, doing femme fatale duty in films like Please Murder Me!, and even sneaking in a post-Bedknobs And Broomsticks spree as Mrs. Lovett in a TV movie take on Sweeney Todd. That doesn’t make it any less thrilling, though, to hear the absolute ice in Mrs. Potts’ voice in the John Frankenheimer conspiracy classic, unflinchingly ordering her brainwashed son (Laurence Harvey) to shoot a presidential nominee in order to secure her masters’ rise to power. Meanwhile, the only aspect of J.P. Fletcher that’s in evidence is the same iron composure that faced down so many bumbling killers over the years: Even as she practically shakes with fury, promising vengeance on her enemies—a very different tale as old as time—Lansbury’s velvet-smooth voice never rises above a pleasant, slightly detached whisper that’s more lethal than a dozen assassin’s bullets. [William Hughes]


6. Steve Martin, The Spanish Prisoner (1997)

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Writer-director David Mamet prefers severe minimalism from his actors, so all Steve Martin really had to do in The Spanish Prisoner was show up and deliver the script’s precisely crafted dialogue, with the proper pace and enunciation. Nevertheless, casting him as the clever con man Jimmy Dell was absolutely brilliant. Mamet takes advantage of the comedian’s famously relaxed, refined offscreen persona, painting it as something easy to admire but inherently shady. As Jimmy tries to sweet-talk an under-appreciated engineering genius (Campbell Scott) into handing over his latest designs, Martin’s the epitome of amoral cool. He pretends to show his mark the secrets of wealth and power, all while picking his pocket. Jimmy’s the engine that drives Mamet’s twisting plot, because he represents everything the hero aspires to be. [Noel Murray]


7. Denzel Washington, Training Day (2001)

Denzel Washington has played his share of mean sons of bitches, but no role has more successfully subverted his natural charisma than his Oscar-winning turn as Alonzo Harris, the dirtier-than-a-dump LAPD cop who takes Ethan Hawke’s fresh recruit on a ride-along to the dark side in Training Day. Seeing Washington’s thousand-watt smile recast as the grin of a black-clad Mephistopheles figure is a shock, but the performance has more layers: Alonzo may be a violent gangster with a badge, but underneath, he’s as psychologically cornered as the corrupt lawman played by Harvel Keitel in Bad Lieutenant. In his final defiant shouts (“I run this shit, you just live here!”), the fear cracks through the braggadocio. [Ignatiy Vishnevetsky]


8. Ben Kingsley, Sexy Beast (2002)

It wouldn’t be fair to reduce Ben Kingsley’s career to variations on sainthood; he’s exhibited enough range (and played enough amoral customers) to escape being typecast as exclusively great men. All the same, many of the English actor’s most iconic roles—his celebrated take on Mahatma Gandhi, his gentle supporting turn in Schindler’s List—have pushed nobility to the forefront. Which is exactly what makes his Don Logan, the psychopathic gangster houseguest of Sexy Beast, such an electrifying outlier. Sent to coax ex-convict Gary “Gal” Dove (Ray Winstone) out of retirement for one last heist, Don is the embodiment of someone’s criminal past catching up with them: a violent, foul-mouthed scoundrel from another lifetime, crawling out of the woodwork and digging his heels in. Speaking with a Cockney sneer, Kingsley savors Don’s flavorful profanity and staccato outbursts. What makes the performance truly scary, though, is the calculating intelligence and strategy behind every tantrum—a quality that links this lunatic, in some small way, to the compassionate activist the actor won an Oscar portraying. [A.A. Dowd]


9. Gregory Peck, The Boys From Brazil (1978)

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Gregory Peck will always be remembered as Atticus Finch, attorney and defender of American ideals of tolerance, decency, compassion, and integrity, who the actor embodied in the 1962 film version of To Kill A Mockingbird. Peck’s sympathetic baritone and nobly chiseled features eventually became so synonymous with moral uprightness that he had to cover them with a German accent and a caterpillar mustache to play one of the 20th century’s greatest monsters, Nazi “Angel Of Death” Dr. Josef Mengele. Even then, Peck can’t quite conceal his essentially decent nature, try as he might under a torrent of actorly affectations. The result is a war criminal who comes off more comically demented than truly sinister, forcing the film to provide living proof of the doctor’s cruelty in the form of “deformed” extras. It doesn’t help that Mengele’s harebrained scheme is to produce a new Adolf Hitler—a complicated gambit of adoption-agency subterfuge and discredited theories about cloning that wasn’t exactly original author Ira Levin’s finest hour either. [Katie Rife]


10. Tom Hanks, The Ladykillers (2004)

An innate sense of decency isn’t all that’s kept Tom Hanks from playing many bad guys. Given his underrated nuance and versatility as an actor, it’s hard to picture a Hanks character as morally uncomplicated, which is where a lot of typical Hollywood villains land (and where his hit man anti-hero from Road To Perdition doesn’t). Goldthwaite Higginson Dorr, the thieving ringleader Hanks portrays in the Coen brothers’ remake of The Ladykillers, is complicated more by his verbosity than his morality; he’s a planner of heists and potential murders, disguised with endless curlicues of dandified civility (and beige outfits). That’s the contrast Hanks, in his first and so far only Coens performance, latches on to, and what makes his work so delightful (and the movie, if admittedly the Coens’ worst, perhaps a few ticks better than its reputation). After a decade of mostly serious parts for a former comic actor, maybe it took going bad for Hanks to look and sound so ridiculous. [Jesse Hassenger]


11. Mary Tyler Moore, Ordinary People (1980)

After portraying one of television’s most-beloved wife and mothers on The Dick Van Dyke Show, Mary Tyler Moore became the career woman who could “turn the world on with her smile” in her own eponymous sitcom. In both roles, she was plucky, good-natured, and, above all else, loving. Just three years after The Mary Tyler Moore Show went off the air, the actor emerged as a cold, perfectly mannered matriarch in Robert Redford’s 1980 directorial debut, Ordinary People, a film about the disintegration of an upper-class family after the accidental death of its eldest son. Part of what makes Moore’s about-face so powerful here is how her old persona still pushes through: Her character’s a grieving woman, chillingly limited in the love she’s able to give her surviving child, who masks her pain beneath a sunny demeanor. It’s a chillingly believable performance. [Laura Adamczyk]


12. Kurt Russell, Death Proof (2007)

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Clichéd as it is to point out, Quentin Tarantino remains a master at resurrecting a faded star’s original appeal. Casting Kurt Russell as the homicidal Stuntman Mike in Death Proof, his half of the Grindhouse double bill, is one of the director’s crown jewels. Tarantino had grown sick of seeing Russell earn plaudits as unambiguous good guys in movies like Dreamer and Miracle, and said he wanted the actor “to be a badass again,” but that’s sort of misstating the type of badass Russell was in the ’80s and ’90s. In the classic John Carpenter films and capers with wife Goldie Hawn, Russell was always raffish and endearing, his eyes sparkling with a touch of playfulness. Death Proof course-corrects his seeming softness with all the grace of a Mustang careening back onto a dirt road, turning that old-Hollywood charm into the first phase of a bizarre, sexualized murder ritual. He’s still cackling with hoo-boy delight, even as he’s torturing women throughout a series of kinetic car chases. But the charisma gets brilliantly inverted when the tables are finally turned, and the supposed badass is reduced to a mewling, bloodied mess. [Clayton Purdom]


13. Macaulay Culkin, The Good Son (1993)

For decades now, the internet has joked about the gleeful sociopathy of Home Alone’s Kevin McCallister, a kid who likes to spend his Christmases rigging up blowtorches, hurling bricks, and cheerfully electrocuting crooks. Thing is, Macaulay Culkin functionally poisoned that comedy well 25 whole years ago, when he signed on to play Henry Evans, the blandly soulless star of Joseph Ruben’s The Good Son. Just like Kevin, Henry is a mechanically gifted youngster with a cherubic appearance; the only difference is that he turns his homemade crossbows and evil plans on his family, instead of bumbling crooks. At the time, critics rightly blasted Culkin for reducing Henry’s evil to little more than a monotone, a smirk, and the occasional ill-advised effort to make “Don’t fuck with me” sound scary coming from a pre-pubescent voice. But in hindsight, Henry’s only real sin is one of timing; had Culkin been given a few more years to get a little more malice under his belt, The Good Son could have been a blackly comic masterpiece instead of a ludicrously melodramatic thriller. [William Hughes]


14. Jim Caviezel, DĂ©jĂ  Vu (2006)

Will Jim Caviezel ever escape the shadow of his most widely seen and appreciated role, the nobly suffering messiah of Mel Gibson’s The Passion Of The Christ? With his terrific time-travel detective yarn Déjà Vu, the late Tony Scott found a way not to disguise the crown of thorns permanently affixed around the actor’s head but to create a new context for it. Not long after The Passion smashed box office records, Scott cast Caviezel as a deranged terrorist bomber who blows up a ferry full of innocent people. As written and played, Carroll Oerstadt is a vengeful zealot and self-proclaimed prophet. “Satan reasons like man,” he proclaims. “But God thinks of eternity.” During their final standoff, the film’s ATF hero (Denzel Washington) pokes a big hole in the villain’s God complex: “You’re willing to sacrifice others, but not yourself.” It’s a brilliant twist on the audience’s powerful new association with Caviezel, one that locates the thin line separating holy conviction from mania. [A.A. Dowd]


15. Ronald Reagan, The Killers (1964)

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Opinions on his presidential legacy vary, but it’s generally acknowledged that Ronald Reagan was a pretty okay actor. Not great, not terrible, just an affable, okey-doke kind of guy. And with his career as a political speechwriter taking off, Reagan—who had converted to the Republican Party only a few years before—decided to try something different for his final screen appearance: his one and only villainous role, as mob boss Jack Browning in Don Siegel’s nihilistic remake of the 1946 noir classic The Killers. One might expect such a character to be played with smoldering intensity and wicked panache, but Reagan plays it unnervingly straight, his mild-mannered sadism perfectly attuned to Siegel’s flat cinematography and blasé approach to extreme (for the time) violence. Whether the actor’s demeanor was a deliberate choice or just a matter of him being out of his depth is up for debate. Reagan would later say he regretted taking the role due to a sexually charged scene where he viciously slaps Angie Dickinson in the face; the film’s depiction of California businessmen as corrupt and amoral, just a few years before Reagan got into California politics, remained uncommented upon. [Katie Rife]


16. Judi Dench, Notes On A Scandal (2006)

In the movie adaptation of Zoë Heller’s novel Notes On A Scandal, Judi Dench plays emotionally distant teacher Barbara Covett who secretly manipulates an embattled colleague (Cate Blanchett) into becoming her friend by using the younger woman’s secrets against her. Much of the story is told from Barbara’s perspective, via thoughts she pens in her diary. It’s a tricky performance, eliciting sympathy from the audience for the sad life of a lonely woman, while also revealing how cruel and selfish she can be. Dench is more than up to the task, showing how the traditional middle-class English sense of propriety at once defines her character’s worldview, prevents her from asking for what she really wants, and transforms her into a monster. [Noel Murray]


17. Kevin Costner, Mr. Brooks (2007)

Kevin Costner’s filmography reads as a who’s who of virtuous men: baseball players, golf players, Robin Hood, Eliot Ness, Wyatt Earp, avatar of the American frontiersman, Superman’s dad. Even when he played a bad guy, as he did in Clint Eastwood’s A Perfect World, he still played a good guy, pressed into a life of criminality. But all of that changed in the exceedingly strange Mr. Brooks, starring Costner as the titular homicidal madman. Placid and methodical, the killer leads a double life as a beloved Portland businessman, only pressured into killing by his id, which is embodied quite literally here by a preening William Hurt. Costner’s inability to convincingly portray Brooks’ dual nature isn’t the film’s only source of unintentional comedy: It’s loaded with weird-ass subplots, like the multimillionaire cop played by Demi Moore who’s hot on his trail, or a wannabe serial killer played with shocking earnestness by Dane Cook. As the plot twists mount, Costner seems incapable of summoning the dark spirit necessary to play the character, his face remaining flat even as he slits Cook’s throat with a shovel. If nothing else, the movie gave us that scene. [Clayton Purdom]


18. Mo’Nique, Precious (2009)

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When comedians get cast in villain roles, it’s usually to play cold-blooded creeps. But Mo’Nique’s performance as Mary, the mother of the teenage title character in Lee Daniels’ overripe kitchen-sink melodrama Precious, plays to the rafters; her character is a jet engine of spite and abusive energy. Mary embodies the scaremongering “welfare queen” sensationalism of the movie’s Reagan-era setting, but she’s more Hollywood than Harlem: a screaming, chain-smoking backstage diva who slips off her head wrap and picks out a wig to play the role of the doting matriarch when the social worker comes around. Her climactic monologue is the film’s For Your Consideration moment (it worked, winning Mo’Nique an Oscar), but is it the character’s confession or her farewell performance? [Ignatiy Vishnevetsky]


19. Patrick Stewart, Green Room (2015)

Like most classically trained British thespians, Patrick Stewart has slipped into a few bad-guy roles; if you can play Macbeth, you can apply your English regality and theatrical poise to a Hollywood heavy—and Stewart did it twice in one year, as the antagonists of 1997’s Conspiracy Theory and Masterminds. But there was still something deeply… wrong about hearing the once (and future) Jean-Luc Picard spew racial slurs as a backwoods neo-Nazi in Jeremy Saulnier’s viscerally violent Green Room. As Darcy, owner of the skinhead bar where a touring hardcore band finds itself holed up and under siege, Stewart doesn’t abandon his signature, almost paternal dignity. Instead, he wields it like a machete, calmly negotiating with his captives from behind a barricaded door, trying to lure them out to certain doom with his comforting, professorial eloquence. In the chillingly refined menace of his performance, one can see a timely portrait of American evil: hate sugarcoated in a smiling “civility.” [A.A. Dowd]


20. Spencer Tracy, Dr. Jekyll And Mr. Hyde (1941)

One of the greatest actors of the black-and-white era, Spencer Tracy almost effortlessly transforms from the moralistic Dr. Jekyll to the evil Mr. Hyde in the 1941 edition of Robert Louis Stevenson’s tale. It was Tracy’s own least-favorite role: He’s about the only one in London without an English accent, for one thing, and his streetwise self seems too coarse to play the upper-crust Jekyll. But Tracy’s legendary cinematic benevolence (having played both Father Flanagan and Thomas Edison by that point in his career) makes his monstrosity all the more brutal, even though his Hyde can be impulsively hedonistic as well as bestial. Still, the film might have been even better using Tracy’s own ideas, like having drugs and alcohol transform Jekyll into Hyde, or having Katharine Hepburn, an actress he hadn’t even met yet, play both the stereotypical “good” and “bad” girls that Jekyll/Hyde gets involved with—personifying the theme that there are benevolent and malevolent sides to us all. [Gwen Ihnat]


21. Jamie Lee Curtis, Mother’s Boys (1994)

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Even discounting her encounters with a certain masked, holiday-obsessed lunatic, Jamie Lee Curtis has been terrorized a lot on screen. With Mother’s Boys, the scream queen finally got to do some terrorizing of her own. One of those yuppies-in-peril “erotic” thrillers that were all the rage in the ’90s (Curtis made another, Kathryn Bigelow’s Blue Steel, a few years earlier, though she was still the stalked there), this justly forgotten, vaguely misogynistic potboiler doesn’t so much connect the Halloween star to her inner Michael Myers as let her do her best unhinged Glenn Close as an absentee parent out to reclaim the family she abandoned. Only a scene of the villain manipulating her own preteen son’s burgeoning hormones truly gets under the skin, but there’s still some fun to be had in the way Curtis subs out her usual warm charisma for a brittle obsession. [A.A. Dowd]


22. Robin Williams, One Hour Photo (2002) and Insomnia (2002)

Eternally restless Robin Williams spent 2002 taking an ax to decades of a carefully cultivated nice-guy image, starring in a pair of films that offered audiences a lurid look at a capacity for darkness at which he’d scarcely hinted before. Of the two, Insomnia’s Walter Finch is the lesser creation; despite Christopher Nolan’s best efforts, the murderous horror writer rarely amounts to much more than “Robin Williams saying serial killer stuff,” which is the same admittedly fascinating gimmick that’s powered any number of Law & Order stunt-casting episodes, including Williams’ own. One Hour Photo’s Sy Parrish is a far more fascinating beast. His wispy-blond hair and face-obscuring glasses threaten to verge on “actor transforms themselves” cliché, but it’s Williams’ ever-present and yawning need to be liked—turned inward and curdled for once—that makes him such a recognizable and tragic monster. [William Hughes]


23. Adam Driver, Star Wars: The Force Awakens (2015) and Star Wars: The Last Jedi (2017)

Adam Driver might be one of the most gifted actors of his generation, but the mass appeal of Star Wars has ensured that a sizeable percentage of moviegoers only know him as the moody Kylo Ren, the most complex antagonist in the saga. But while the tall, gawky Noah Baumbach regular can be equally memorable in big and small roles, nothing about his film career outside of The Force Awakens and The Last Jedi screams “space villain.” He’s the blue-collar poet of Paterson, the good cop of BlacKkKlansman, the scene-stealing cowboy bass to fellow Star Wars cast member Oscar Isaac’s cash-strapped folk singer in Inside Llewyn Davis. But he brings an unlikely relatability to the role of Kylo Ren, playing the frustrated Darth Vader wannabe as a tragic character; in a series that’s gone on and on about the corrupting power of the Dark Side, Kylo’s turn to evil is the only one that’s believable. Star Wars is full of iconic roles, but Driver’s might be the most dramatically compelling. [Ignatiy Vishnevetsky]