'90s Heartthrobs Who Played Despicable Villains - And Nailed It

When Heath Ledger was selected to play the Joker for Christopher Nolan’s The Dark Knight, critics and moviegoers alike weren’t too sure the hyper-charming and handsome heartthrob could pull it off. Luckily for audiences everywhere, Ledger’s last performance before his tragic demise was perhaps his best - and put his range on full display.

Ledger’s fresh take on the classic character is undeniably vicious and manages to make swooning audience members everywhere forget just how handsome the Aussie was under his messy makeup. 

One could easily argue Leonardo DiCapro deserved an Oscar for his absolutely haunting and hateful turn as slave owner Calvin Candie in Quentin Tarantino’s Django Unchained. According to several interviews, the moment when Calvin smashes his hand on the dinner table, Leo crushed a small, stemmed glass with his palm and began to bleed. Instead of drawing attention to the injury, he stayed in character, and the take was used in the final print of the film.

Of course, it wasn’t always this way. After his performance as Jack Dawson in Titanic, this quintessential '90s heartthrob became a superstar overnight - and was single-handedly responsible for kick-starting puberty for thousands of millennials.

Christian Bale is well-known for his range, so it’s not too surprising that he was cast to play the homicidal Wall Street executive Patrick Bateman in the cult classic American Psycho, even if he was originally known for feel-good films like Newsies and Little Women. Bateman is a character so defined by appearance and vanity that the very British Bale (read: loves a pint and a cigarette with lunch) had to trade the pub for three-hour sessions with a personal trainer to bulk up to meet his character’s aesthetic.

It’s Bateman’s looks and status that keep him out of the spotlight (and prison) over the course of American Psycho, though by the film’s end, it’s unclear if Bateman has ever committed a single murder. At the very least, he's guilty of keeping a super creepy journal.

Skeet Ulrich broke into Hollywood in a big way in 1996 when he starred in Boys, The Craft, and his biggest role, Scream. Ulrich’s Billy Loomis is a pitch-perfect trope of the classic horror movie high school boyfriend. He pouts sexily as he complains that Sidney, his virginal girlfriend, won't give it up, and at one point tells her she's sulking too much over her deceased mother. What a nice guy.

Billy uses his good looks to his advantage, and his relationship to Sidney is a solid smokescreen... until he decides it’s time to reveal his master plan.

Best known as vampire-killing Buffy in '90s WB favorite Buffy the Vampire Slayer, Sarah Michelle Gellar lights up the screen as the dreadfully manipulative, downright sociopathic Kathryn in the beloved (and super dark) teen drama Cruel Intentions. Shedding her girl-next-door vibe for a much darker personality (and hair), Kathryn schemes and plots the downfall of a virginal Annette (Reese Witherspoon) with the help of her stepbrother Sebastian (Ryan Phillippe). If Sebastian succeeds in his seduction of Annette, thus handily destroying her reputation at school, then he'll get what he's always wanted: to sleep with his stepsister. Diabolical.

It only gets worse for Kathryn when Annette and Sebastian personally insult her by falling in love. Hell hath no fury like SMG scorned.

In The Bad Batch, a dystopian thriller written and directed by Ana Lily Amirpour, genuinely good guy and fan favorite Keanu Reeves uses his good looks in a pretty believable way - as a cult leader surrounded by a harem of young, pregnant women. He plays the Dream, a man in charge of his own town in a dystopian, cannibalistic, Mad Max-esque hellscape, yet his town of "Comfort" eventually reveals itself to be a lie.

Although the film can be a little self-indulgent and pretty slow, it’s a lot of fun to watch Keanu as the bad guy, especially when he goes into detail about his town’s plumbing. Yes, that's real.