Cruel Intentions (1999)

These days, it’s very common to see same-sex couples and moments in movies and TV. However, even back in 1999, it was still relatively uncommon. So, you can imagine the uproar a steamy teen drama like Cruel Intentions. The film follows two wealthy socialite siblings, played by Sarah Michelle Gellar and Ryan Phillipe, who romantically and sexually toy with two young women, portrayed by Reese Whitherspoon and Selma Blair.

In one scene, Blair’s character admits she’s rather inexperienced with kissing. In response, Gellar’s Kathryn Merteuil offers to teach her how to kiss. The result is one of the most charged scenes ever put on celluloid – and plenty of fingers on the pause button.