It can’t be denied—there is a certain thrill in seeing an actor that you love throw off their halo and dive into the dark side of their character. It’s the ultimate cinematic betrayal: the trustworthy face you’ve seen for years turns to something scary. The one thing that goes really well with it is seeing the Hollywood charming guy or the nice girl character being corrupted spectacularly. The film industry has always been fond of the unexpected twist, and there are not many options to compare with that featured, where a formerly lovable actor spikes into villainy to the delight and horror of the audience. Below are ten of the most memorable times in movies when characters in the kindest forms suddenly revealed the dark side, ranked from the most understated to the most astonishing.
10. Rosalind Russell in The Velvet Touch (1948)
Rosalind Russell, who is generally associated with bright comedies and her sharp satire, has, in The Velvet Touch, shocked the viewers with a sneaky role full of moral ambiguity. Playing Valerie, a Broadway star tramped in the mire of envy and homicide, Russell’s character showed less and less of her winning ways and more of her dark side. She not only used her gorgeous outfits and razor-sharp talk to show off her one-of-a-kind “diabolical diva” but also demonstrated her capacity to be a “comedic queen” as effortlessly with the same line of work.
9. Kay Francis in In Name Only (1939)
After being the good, victimized heroine for many years, Kay Francis only got the chance to portray a character on the wrong side of the fence, and she did it with absolute gusto. In Name Only features Francis as Cary Grant’s crafty and money-hungry wife who is willing to do whatever it takes to live a life of luxury. This play of her career repositioned her and made the audience see that Francis was not only the tragic beauty in a biased cut dress but also voluptuously wicked.
8. Robert Montgomery in Night Must Fall (1937)
Famous for his smooth Playboy and light-headed charmer roles, Robert Montgomery surprised MGM when he insisted on portraying a killer. The outcome? His ice-cold performance as Danny, a psychotic charmer who conceals his ugliness beneath a grin. Montgomery was so convincing that he was nominated for an Oscar and totally rewrote his screen persona. His performance is one of early Hollywood’s most unsettling depictions of charisma turned bad.
7. Jean Simmons in Angel Face (1953)
Jean Simmons might have loathed making Angel Face, thanks to the iron-fisted direction of Otto Preminger, but her acting is noir perfection. As the dainty-looking heiress Diane Tremayne, with a deadly secret, Simmons employs her innocent face as camouflage for raw danger. Together with Robert Mitchum, she’s both seductive and terrifying—a femme fatale for the ages.
6. Gregory Peck in The Boys from Brazil (1978)
Gregory Peck, Hollywood’s moral conscience after the triumph of To Kill a Mockingbird, was unexpectedly the opposite when he announced that he would portray Josef Mengele, the Nazi doctor, in The Boys from Brazil. It was very disturbing at the very core to watch the man who represents justice and humaneness allow himself to be drawn into the realm of evil. Peck was finishing up an intentional shift of the perception of himself as a character actor—but to viewers, it was like witnessing Atticus Finch setting fire to his own courtroom.
5. John Wayne in Red River (1948)
Before Red River, John Wayne was the very image of the good side of the wild west, with a strong and kind character. Nevertheless, as Tom Dunson, a cattle baron with a tyrannical streak and the need to control everything, Wayne revealed another, shadowy, but mature and richer side. He did so with such skill and finesse that even his methods of cruelty were turned into a side of his depth and complexity, and he ultimately proved that he was not just a one-trick cowboy. It was this one that even got John Ford to concede that Wayne was really an actor.
4. Ronald Reagan in The Killers (1964)
Long before the White House, Ronald Reagan stunned fans with his casting as Jack Browning, a ruthless gangster in Don Siegel’s The Killers. It was his final film, and his sole real villainous role, and he pulled it off. Reagan despised playing a slimeball, but the performance is chilling all the more because he’s so convincing as a man of authority with no conscience.
3. Henry Fonda in Once Upon a Time in the West (1968)
Few casting decisions in cinema history have stuck harder than Henry Fonda’s becoming Frank, the blue-eyed devil of Once Upon a Time in the West. From his traditional role of playing proper, all-American heroes, Fonda swallowed Sergio Leone’s bait and went all bad. The first time he kills a child on screen, audiences gasped—first because of the act, then because Henry Fonda did it. It was cinematic whiplash of the highest degree.
2. Andy Griffith in A Face in the Crowd (1957)
Before Mayberry and sermons on morality, Andy Griffith was Lonesome Rhodes—a manipulative drifter turned media populist. His introduction in A Face in the Crowd is a searing examination of glory, charisma, and corruption. Griffith’s brilliance is electric and terrifying, showing how quickly the adoration can turn to manipulation. Watching it now, it is still very relevant.
1. Tony Curtis in The Boston Strangler (1968)
At the top of this list is the charming Tony Curtis, the lovely face of cinema, who disappeared into one of the darkest and most unpleasant things of the 1960s. As the Boston Strangler’s serial killer Albert DeSalvo, Curtis stripped off the last traces of glamour. His low-key and disturbing acting, especially the frightful mime sscenestunnedde the critics. Director Richard Fleischer’s telegram after the premiere wrote it best: “I am vindicated.”
So these are the ten times when the heroes of the golden age of Hollywood switched to the dark side and proved that “nice” is not the same as “safe.” These roles not only shocked the fans but also prolonged the actors’ careers, broke down the fans’ stereotypes, and reminded everyone that the most unsettling villains are the ones who wear the friendliest smiles.