Today marks 15 years since the release of Cruel Intentions on March 5, 1999. A tale of teenage lust and deceit, the film’s considered a cult classic and managed to stand the test of time unlike other forgettable movies from that era.
And since we at TSS are suckers for nostalgia, we’ve decided to share eight reasons to watch this flick and be reminded how it was sex education for tender eyes. Grab your popcorn and let’s take a trip down memory lane.
1. Sebastian Cements Himself As A Legend
“You’re a very attractive woman. You have killer legs. I’d like to photograph them.”
Therapy can reveal how much of a dirtbag you are. Such is the case with Sebastian, played by Ryan Phillippe, during his final session of soul searching. Sebastian’s budding career as a racy photographer wouldn’t coincide well with the therapists upcoming book tour, that’s for sure.
2. The Bet
“In English, I’ll f*** your brains out.”
Being the ultimate womanizer that he is, it’s no surprise when Sebastian shares his goal of screwing his school headmaster’s daughter before the first bell for class rings with his step-sister, Kathryn, played by Sarah Michelle Gellar. Kathryn’s offer seems a little one-sided for our liking, after taking a second glimpse at Sarah Michelle in all of her seductive glory, we can honestly admit that’s an offer that many men couldn’t refuse, us included.
3. Girls Kissing Girls
There’s Cecile, an impressionable classmate who’s possibly the dumbest girl in recent cinematic memory, who’s never made it first base with a guy. Kathryn, being the ‘friend’ that she is, decides to offer a first hand tutorial in the art of lip locking, letting the world in on the secret that girls “do it all the time, how do you think we learn?”
A huge chunk of the TSS faithful were probably a bunch of horny teens when this scene first crossed our radars and on their behalf, we’d like to thank the directors for blessing us with one of our first glimpses of girl-on-girl action.
4. Sara Michelle Geller Being The Ultimate Tease
In the teen flick renaissance of the late ’90s, few teen stars were considered as hot as Sarah Michelle Gellar. Known for her girl next door appeal, this erotic scene gave the fellas even more reason to thirst. While many men felt Sebastian’s pain of being left hanging after the ride of his life, most still would’ve paid the admission, as Sarah, umm Kathryn, was a walking wet dream waiting to happen.
5. The Black Guy Gets Fired, As Usual
“Don’t give me any of that racist crap. My husband and I gave money to Colin Powell!”
Mrs. Caldwell goes all Paula Dean on Cecile’s music instructor Ronald after finding out about her daughter’s secret relationship with him. This scene is a hilariously accurate account of how some of the wealthy think of minorities and could be mistaken for a Chappelle Show skit if you weren’t paying attention.
FYI: His “Got me off the streets? I live on 59th and Park (Avenue)” retort will never fail to be hilarious.
6. The Secret Society Dance
“Cecile, you had an orgasm. You’re becoming a woman. I’m so proud of you.”
After getting her flower bloomed by Sebastian, Cecile decides to confide in Kathryn for advice. The seasoned slut that she is, Kathryn urges Cecile to continue these sexual clinics with Sebastian cause as they say, practice makes perfect. Comparing causal sex to a secret society is pretty spot on, but Cecile’s horrible dance celebrating her induction is definitely not.
7. The Queen B Wins
“I don’t f*ck losers”
While we’re all for fun and games, it takes a real petty person to purposely derail a chance at love for personal amusement, but that’s Katherine. Her rottenness aside, the look on Sebastian’s face is meme worthy to say the least.
8. Pay Back Is A Bitch
What’s done in the dark eventually comes to light, and Kathryn’s fuckery is no different. During Sebastian’s funeral, her deceitful ways come back to haunt her in the form of Sebastian’s journal, converted into a book for her classmates reading pleasure. Her cherished reputation destroyed and with her coke-filled cross no longer a secret, Kathryn ends her run as one of the most notorious b*tches of this generation.