Teen Idols Who Played Vile Villains - And Nailed It

Biggest Heartthrob Role: Patrick Verona in 10 Things I Hate About You

When He Went Dark: As you might surmise by the name Patrick Verona (read: Shakespeare's Romeo and Juliet setting), Ledger's 10 Things I Hate About You character is based on The Taming of the Shrew character Petruchio. As is often the case with teen rom-com leads, he's the kind of guy who's a bad boy with a heart of gold. (Pro tip for teens everywhere: This vibe does not exist IRL.)

Nine years later, Ledger took on the most iconic role of his career in The Dark Knight. Ledger's iteration of the Joker is one of the most celebrated versions of the character of all time. Sadly, the role ended up being his last fully finished acting job before his death that same year. 

Between the slight accent and his striking face paint, Ledger got so into character that you likely wouldn't even notice it was him without already knowing he was wearing the iconic purple suit. He manages to toggle between the unhinged portrayal of the Clown Prince of Crime while also nailing pseudo-board room scenes with his particular brand of chaos added to the mix.

When he's not killing a dude with a pencil, the Joker is goading Batman while he's dangling out of a high-rise building. The Clown Prince is as fearless as he is ruthless and the charisma Ledger brought to the role makes him stand the test of time. 

Biggest Heartthrob Role: Buffy Summers in Buffy the Vampire Slayer

When She Went Dark: In 1999, Sarah Michelle Gellar went from using crosses against vampires in Buffy to snorting coke out of one on-screen in Cruel Intentions. And yes, it's just as iconic as it sounds. 

The actress' debut in Buffy the Vampire Slayer changed the game for women in TV, giving fans a bada** female lead who dusts vampires in heels and peak '90s fashion. Naturally, Gellar had the whole being a heroin thing down, but two years into her role as Buffy, she got a taste of the wild side. 

Gellar's character Kathryn Merteuil is basically a high schooler's worst nightmare. Not only does she seduce and sexually gaslight her ex's new girlfriend in a long-winded attempt at revenge, but she's also the mastermind of a bet that her step-brother can't seduce an innocent girl. So, what's on the table for the winners? Glad you asked. Kathryn gets his Jag if she wins and Sebastian gets Kathryn. In his bed. You know, his step-sister. 

From there, things get even more twisted as the lines of family get blurred and Kathryn's warpath turns deadly. It's no surprise that Gellar nailed the role of feigning innocence while hiding a devious and controlling streak underneath. Buffy also required her to play a dual, faceted character. Though they're both on opposite ends of the spectrum in the villain and hero departments, there's definitely some overlap.

Biggest Heartthrob Role: Ted Logan in Bill & Ted's Excellent Adventure 

When He Went Dark: As is often the case when people are about to fail history, Keanu Reeves's Ted travels back in time for a hands-on history lesson in Bill & Ted's Excellent Adventure. Of course, he's too busy with his band to pay attention to school, but it's okay, because his band is the precursor for a future utopia, obviously. 

Though Reeves's most well-known early role is arguably The Matrix, that early one helped cement his foundation in Hollywood. Years later in 2015, Reeves quite literally put on a villainous trucker hat when he played Donnie Barksdale in The Gift. 

Though Barksdale isn't the main villain in the movie, he's an awful abusive husband. To make matters worse, he's an antisemitic and racist bigot. It's always impressive when a kindhearted guy like Reeves can take on such a despicable character. Barksdale's domestic violence is obviously hard to watch and hits way too close to home for these very real people who exist in reality. 

Biggest Heartthrob Role: Jack Dawson in Titanic

When He Went Dark: Fans have been trying to draw Leonardo DiCaprio like one of their French girls since 1997. The actor played Jack Dawson in one of the most tragic on-screen love stories of all time in Titanic. 

For anyone who lives under a rock (or a glacier), the movie (based on the real sinking of the Titanic), portrays the fictional relationship between wealthy girl Rose and poor boy Jack aboard the ship. It wasn't DiCaprio's first dance as a star-crossed lover, though. One year before Titanic, he played Romeo in Romeo + Juliet, the modernized adaptation of the classic play. 

DiCaprio is particularly drawn to period pieces, but he's not always partying in the ‘20s. In Django Unchained, the actor heads back to the few years before the Civil War to play horrid plantation owner Calvin Candie. To make matters worse, Candie calls his plantation “Candyland,” which just feels … gross in so many ways. The horrors don’t end there, though. The villain runs what is essentially a forced fight club between his male slaves that he charges spectators to watch. 

The most sinister component of this particular villain comes from the fact that he doesn't have any special powers and he's not simply a figment of a writer's imagination. History was and is full of deplorable men like this who use wealth to treat people like they're sub-human. Candie's typical soft-spoken Southern drawl is chilling as it calmly contrasts the character's brutality and lack of humanity. That is, when Candie isn't actively getting violent himself. 

Biggest Heartthrob Role: Troy Bolton in High School Musical

When He Went Dark: Zac Efron has long since proven himself since his Troy Bolton days singing in the East High halls, the school gym, the theater, the pool, a random rooftop greenhouse… really, is there any place in Albuquerque this dude hasn't belted in? Efron charmed the world with a unique combo of jock-meets-theater-nerd to appeal to everyone no matter which clique they sit (sing) with at the lunch table. 

In 2019, Efron took on the role of Ted Bundy, one of the most notorious serial killers of all time. Viewers were particularly unnerved by his performance in Extremely Wicked, Shockingly Evil and Vile as he effortlessly emulated the terrifying killer. 

Anyone who's done deep dives into Bundy has probably seen footage of the trial where he represented himself on the stand (also depicted in the film). There are several moments when real-life Bundy dropped his charismatic performance and there was just… nothing. It was almost like he was a blank vessel with no emotion or a drop of humanity - and it's something that continues to haunt people generations later. Watching those moments is just about the closest we can get to seeing the concept of having a soul (or lack thereof) present itself in a tangible way.

Efron had no problem toggling back and forth between the many facets (or illusions) of Bundy's personality - whether it's charming the masses, failing to hide his cold and angry side, or the somehow more sinister nothingness that sometimes slips through. While some people cited the movie as glorifying Bundy's killings, the movie is told from the point of view of Bundy's ex-girlfriend Liz (whose real-life counterpart was a part of the filmmaking process). 

Despite knowing precisely how this story ends, Efron's charm almost convinces you that his character is innocent - but that's the point. He's supposed to fool the audience for a second the way the real Bundy fooled everyone for years. It becomes abundantly clear that it's a facade and the character study dives deep into the psychopathy of a killer later on. No one is left thinking that Ted Bundy is anything but a callous killer at the end.

Biggest Heartthrob Role: Blane in Pretty in Pink

When He Went Dark: When it comes to rom-com love triangles, Andrew McCarthy's Blane in Pretty in Pink is one of the most controversial. Though plenty of fans root for Duckie to woo Andie, there's no denying that the movie helped launch McCarthy's heartthrob status even if his character was kind of a jerk. 

Content warning: Rape, domestic violence, and kidnapping

It's rare for a one-off villain in a series with over 26 seasons to make such an intense impact, but McCarthy's role as Randolph Morrow in Law & Order: Special Victims Unit has stood the test of time. He appeared in the episode “Slaves,” and the horror is pretty apparent by just the title. 

Not only was his character awful and abusive to his wife, but things get much, much more horrifying when he kidnaps a woman named Illena, keeping her as a sex slave. He forces her to live in a closet and under his bed, and she wasn't the first. He isolated the women and went as far as killing their loved ones. The series is generally hard to watch due to the perverse nature of the villains, but this was particularly brutal. McCarthy made this already heinous character even more formidable and he's stuck with viewers over 20 years later.

If you or a loved one is experiencing domestic violence or sexual assault, the number for the domestic violence hotline is 800.799.SAFE (7233) and the number for the sexual assault hotline is 800-656-HOPE (4673).