I’ve got a soft spot for Cruel Intentions—the original film has that je ne sais quoi blend of charm, scandal, and a twist of pure venom that only Kathryn Merteuil could perfect. While I’m ...

DEADLINE: So, you’re not playing Kathryn and Sebastian ... and just adding this new chapter in the Cruel Intentions universe. DEADLINE: What was the cruelest thing your characters did this ...

We talked on the way up, and she was a cool chick,” he remembered. Cruel Intentions cast Gellar against type as Kathryn Merteuil, a scheming heiress who makes an illicit wager with her step ...

Then, boy, do we have a bombshell for you: Cruel Intentions just turned 20 ... enter a bet with his step-sister Kathryn (Gellar) to seduce their headmaster’s daughter, Annette (Witherspoon).

The friends stayed socially distanced for the smooch, 20 years after they first won an MTV Movie & TV Award for the iconic kiss Benjamin VanHoose is a Staff Editor on the Movies team at PEOPLE.

A thrilling and relentless game of cat and mouse comes to life in Cruel Intentions: The Musical, when the gorgeously despicable step-siblings Sebastian and Kathryn set a wager on Sebastian's next ...