With The Gray Man now available on Netflix, Chris Evans shared that the Russo brothers made playing a villain a lot more fun. Of course, his latest role deviates from Evans’ “good guy” image after playing the patriotic and heroic Captain America for eight years.
Even before his role as Lloyd in the latest action thriller, Evans also played the antagonist in 2019’s Knives Out, which further shows the actor’s efforts to demonstrate his versatility in much darker roles. Evans is not the only actor to break away from this “good guy” typecast, with actors like Robin Williams and Denzel Washington challenging themselves on meatier roles and subverting the audience’s expectations.
Sarah Michelle Gellar – Cruel Intentions (1999)
Sarah Michelle Gellar is arguably still best known for her heroic role as the titular monster hunter in Buffy the Vampire Slayer, but she also made a name for herself as a slasher movie scream queen in movies like Scream 2 and I Know What You Did Last Summer. She also took on the revamped role of Daphne for the live-action Scooby-Doo films, learning how to kick-butt against the monsters she faces.
Somewhere in between these though, Gellar starred as Kathryn Merteuil in the teen drama Cruel Intentions. Kathryn is a cruel and manipulative woman, far removed from roles like Buffy or Daphne. Cruel Intentions has gone on to gain a cult following, in large part due to Gellar’s villainous turn.
Iwo Uwais – The Night Comes For Us (2018)
Exploding onto the movie scene with genre-defining The Raid: Redemption, Iko Uwais quickly made a name for himself as one of the best martial arts actors of the generation. Many of his films to date have played Uwais as the hero, even if one with a morally dubious past.
However, The Night Comes For Us asks the question of how terrifying would it be if Uwais were the “bad guy.” Uwais plays an assassin at odds with The Raid co-star Joe Taslim in this unrelentingly violent film and makes him surprisingly sympathetic and scary at the same time. Uwais holds nothing back as the ambitious gang enforcer and makes sure that the action can stand alongside the best fight scenes from The Raid.
Robin Williams – One Hour Photo (2002)
A household name in comedy, Robin Williams needs little introduction. Endearing himself to generations of fans with movies like Mrs. Doubtfire, Jumanji, and Aladdin, Williams managed to mix heartfelt moments with pure comedy in almost all of his movies. He did branch out into dark roles a few times though, most notably with One Hour Photo.
In the film, Williams plays a somewhat disturbed man who works as a photo technician. While he seems to be a friendly, albeit lonely person, he slowly becomes more obsessed with a seemingly idyllic family and begins stalking them. It could be argued that Williams is not a true “villain” per se, but it was strange to see such a beloved comedian in an almost horror movie.
Kurt Russell – Death Proof (2007)
Kurt Russell has been a Hollywood favorite for years, often as the rugged and charismatic leading man in everything from The Thing and Tombstone to Escape From New York and Used Cars. Kurt Russell’s filmography has always been varied, but his role in Quentin Tarantino’s Death Proof was a departure even for him.
Russell plays a murderous stuntman in the throwback to old exploitation movies, particularly hunting down and murdering young women in his supposedly “death proof” car. Russell plays the role with typical coolness but with a hint of malice underneath, not often seen in his other work.
Bryce Dallas Howard – The Help (2011)
Bryce Dallas Howard is known now mostly for leading the Jurassic World franchise and for her directing, and most of her acting roles have been either as protagonist or love interest in movies like The Village, Spider-Man 3, and Black Mirror. She had played a villain in the Twilight series before, but it was The Help that really put her into the antagonistic spotlight.
Howard plays Hilly Holbrook, a rich and racist socialite who spends the film terrorizing the other characters, including her celebrity look-alike Jessica Chastain, with her status and childlike behavior. Hilly was a far cry from Howard’s usual likable characters, and though The Help has received some criticism in years past, its performances are very highly regarded.
Gregory Peck – The Boys From Brazil (1978)
Gregory Peck was one of Hollywood’s leading men for decades and has gone down in history as one of the greatest movie stars of all time. He is best known for his wholesome or strongly principled characters in movies like Roman Holiday and To Kill A Mockingbird.
Peck’s role in The Boys From Brazil, however, could not be more different. In this spy thriller, Gregory plays none other than Josef Mengele, the Nazi doctor behind the atrocities at Aushwitz. Peck plays a sinister and manipulative villain in Mengele and even won a Golden Globe for his performance. It was a surprisingly effective change of form for such a beloved actor.
Denzel Washington – Training Day (2001)
Training Day is one of the more well-known examples of an actor branching out into a villainous role, with Hollywood heavyweight Denzel Washington stepping into the shoes of corrupt police officer Alonzo Harris. Washington, known mostly for his leading roles in dramas and thrillers, crossed over to the other side of the law in this role.
Washington’s dramatic skills translated phenomenally to the role, as his portrayal of Harris is intimidating, charismatic, and thrilling to watch. The role earned Washington an Academy Award for Best Actor, a rare feat for an actor playing a film’s antagonist instead of its hero.
Steve Carrell – Foxcatcher (2014)
When most people think of Steve Carrell, they likely think of The Office’s bumbling but well-intentioned Michael Scott or one of his other great comedic roles. What they likely do not think of is Foxcatcher, in which Carrell turns in a chameleonic performance as eccentric millionaire John du Pont.
Carrell is almost unrecognizable as du Pont, and the film follows him as he builds up his questionable wrestling empire to his real-life murder of wrestler David Schultz. du Pont is not the typical villain, portrayed as more dangerously troubled than truly evil. But it is still a stark contrast to the rest of Carrell’s work and landed him an Academy Award nomination for Best Actor.
Rodney Dangerfield – Natural Born Killers (1994)
Rodney Dangerfield was a beloved comedian and actor who could bring laughs out of just about every situation. Most of his film roles played as extensions of his stage persona and never strayed too far from comedy. That all changed with his role in Natural Born Killers.
In what is surprisingly one of Dangerfield’s best roles, he gives a satirical and disturbing performance as Mallory’s abusive father. His introductory scene is shot as a sitcom, and at first, Dangerfield seems to be his typical goofy caricature until his true, horrible dark side is very quickly revealed. After Natural Born Killers, few will be able to look at Rodney Dangerfield the same way again.
Henry Fonda – Once Upon A Time In The West (1968) 
Arguably the most famous good-guy-turned-villain acting performance of all time, Henry Fonda massively broke form in Sergio Leone’s western classic Once Upon a Time in the West. Fonda was legendary for his morally upright characters in movies like 12 Angry Men and The Grapes of Wrath.
In Once Upon a Time in the West, Fonda does a complete heel turn. Instead of his usual good-natured hero, Fonda’s villainous Frank is a sadistic outlaw with penchant for murder and betrayal. The opening scene of an entire family being killed only to reveal Henry Fonda behind the gun has gone on to become a famous twist in the genre.
