Cruel Intentions was one of my favourite movies as a teen – between the incredible cast, the on point soundtrack, and the extreme naughtiness of the plot, it had everything my adolescent heart could desire. But I haven't revisited it in years, so I thought I'd see how well it stood the test of time. Here's how the experience of rewatching it went down...
1. Omg “Every You Every Me” by Placebo! Suddenly I’m 13 again.
2. ~COZ THERE’S NOTHING LEFT TO DO. EVERY ME AND EVERY YOOOOOU.~
3. I never even realised this movie opens on a cemetery, before panning to Sebastian in his car. Talk about FORESHADOWING.
4. Ryan Phillippe is so pretty here. Between this and that shower scene in I Know What You Did Last Summer, he played a huge part in my sexual awakening.
5. *Ryan Phillippe mentions sex* *13-year-old me giggles*.
6. “You have killer legs. I would love to photograph them.” Oh my god, what a little creeper, hitting on this adult psychologist.
7. Who is terrible at her job btw.
8. I forgot Tara Reid was the psychologist’s daughter hahahaha. This is the greatest acting she’s ever done. (No offence, Sharknado 5.)
9. Fuuuck Sebastian leaked her nudes? I do not remember this. Wow. Wow. And we’re supposed to root for him?
10. “How could you be so stupid?” Way to victim-shame! This woman is not only a terrible psychologist, she’s also a terrible mother.
11. Damn, I thought this scene where she’s screaming at him was so funny as a teen. But he is an ASSHOLE.
12. An asshole with a cool car.
13. Brunette Sarah Michelle Gellar! She looks so good with dark hair. And blonde hair. She just looks good all the time.
14. Aw, baby Selma Blair!
15. “What are the boys like?” Cecile is a girl after my own heart.
16. “How are things down under?” Again, 13-year-old me thought this was hilarious, especially as an Australian (the fact my country was actually mentioned in a movie I liked was a revelation).
17. Ryan Phillippe needs to chill with the over-acting.
18. WoWoW this low-key racism.
19. Gossip Girl borrowed so much from this movie, hey.
20. Sarah Michelle Gellar is iconic in this role. That bustier alone is forever singed into my memory.
21. Fun fact: I had to sneak into the cinema with a friend to watch this, because they said we were too young, and now I finally understand why.
22. “Turn to page 64.” Missed opportunity to make that page 69.
23. Shit, there’s so much casual homophobia in this.
24. “You can put it anywhere.” This went way over my head the first time. I had no idea the catalyst for the whole damn plot was Sebastian wanting to have anal sex with his step-sister. Okaaaaay.
25. This bet is really, really fucked.
26. There was so much exposition dumped in that scene. Even as an adult, I’m not sure I fully comprehend the relationships between all these people, or why any of this matters beyond Sebastian and Kathryn just being selfish, manipulative jerks.
27. Hey, baby Reese Witherspoon!
28. “Sebastian must be home.” He doesn’t even live here?
29. I don’t believe for a second that Aunt Helen makes her own ice tea.
30. He’s accusing her of being a lesbian because she’s not interested in sex. Oh my GAWD this fuck boy.
31. Baby Reese is shutting him down, I love it.
32. These two do have such good chemistry. I remember being so invested in their romance, both on and off-screen.
33. Sarah Michelle Gellar’s facial expressions in this movie are so entertaining.
34. JOSHUA JACKSON. BLONDE JOSHUA JACKSON.
35. I forgot Cruel Intentions was the reason we had to suffer through Pacey Witter’s “frosted tips”.
36. “I fingered his girlfriend at homecoming last year.” The most high school line in this whole damn movie.
37. “Man’s got a mouth like a hoover.” I am now realising I completely didn't understand at least 55% of the dialogue when I was younger.
38. Every male in this movie is terrible.
39. Sarah Michelle Gellar is having a picnic in the park, but she’s dressed like she’s going to a funeral. What a queen.
40. I definitely bought sunglasses just like the ones she's wearing.
41. Here we go with the infamous same-sex kiss! I didn’t realise there was so much casual homophobia in here, and meanwhile they peddle out this kiss for titillation. Ugh.
42. Wait, was that it?
43. Oh, no, they’re going again.
44. “This time, I’m going to stick my tongue in your mouth. And I want you to massage my tongue with yours. And that’s what first base is.” *13-year-old me takes notes.*
45. There’s so much tongue on my screen right now.
46. THE SALIVA!
48. Sebastian is playing “Lovefool” for Annette. This soundtrack is actually the soundtrack of my youth. Well, this and also all the songs from 10 Things I Hate About You. With a bit of Dawson’s Creek thrown in for good measure.
49. That is a nice-ass backpack he bought her with her name engraved on it.
50. I remember thinking flip phones were SO COOL. What a time.
51. Sebastian is a sexual aggressor, I hate him.
52. But also this scene of him in the pool with Annette was definitely an important part of my sexual awakening. Hoo boy I feel so confused right now.
53. YES REESE. STAY AWAY FROM HIM.
54. Don’t fall for it, Reese. Don’t fall for these moves.
55. Ugh he is so hot though. I’m mad.
56. “Listing my qualities on your fingers is not going to get you anywhere with me.” DRAG HIIIIM REESE.
57. “Don’t get so huffy.” Oh man, I used to quote that at my friends all the time.
58. This whole scenario of blackmailing this guy by threatening to out him, and getting him to put in a good word for Sebastian with Annette, is so problematic.
59. It’s like the plot of Love, Simon, but so much worse.
60. The Gregster is an asshole though.
61. Cecile does not remotely resemble a real teenage girl, no matter how sheltered.
62. Now Sarah Michelle Gellar is wearing snakeskin dress. SYMBOLIC.
63. Okay. This scene between Kathryn and Sebastian also played a significant part in my sexual awakening. Like, I did not fully understand what was happening the first time I watched it, but I was into it.
64. Why is Reese Witherspoon putting hand cream on her elbows like she’s a bored sitcom housewife?
65. Oh great, more racism.
66. “Email is for geeks and pedophiles.” 1999 was such a different time.
67. “We’re destroying an innocent girl, you do realise that.” Ooh look Sebastian is already ~changing~.
68. “God forbid I exude confidence and enjoy sex… I’m the Marcia fucking Brady of the Upper East Side.” This speech is AMAZING and ICONIC. Best part of the movie tbh.
69. Wait, so Sebastian got Cecile drunk and is now guilting her into sexual activity, and it’s being played for laughs, and he hasn’t changed much after all, and oh my god this movie is a mess.
70. I AM SO UNCOMFORTABLE.
71. This bit at the retirement home is kind of amusing. Mostly because Sebastian is suffering.
72. Don’t fall for this, Annette!
73. Oh, she isn’t. I love her.
74. She’s pulling faces to make him smile! Dammit, this is cute, and I’m grinning against my will. Much like Sebastian.
75. The hand grab while he’s driving! WHY AM I SMILING AT THIS, HE IS THE WORST.
76. This conversation between Kathryn and Cecile about the latter’s encounter with Sebastian is so off. I’m clutching my pearls for my own younger self, learning about orgasms THIS WAY.
77. Cecile is just casually chilling with a bowl of cherries. Not on the nose at all.
78. This kiss between Sebastian and Annette is so awkward. Is it meant to be hot? He’s eating her face.
79. I wonder if Ryan and Reese’s kids have ever watched this movie.
80. “I just can’t take your games anymore.” Fuck this guy.
81. “You make me feel inadequate.” FUCK THIS GUY.
82. Nothing in the plot has justified either of them being in love yet, but okay.
83. I’m so sad she fell for his manipulative turdburgers.
84. Even though when I was a teen, and she locked that door, I was like YESSSSS.
85. He can't sleep with her. Thank god. I thought this was when their first time happens and I was about to scream.
86. Poor Annette. But also, you escaped, bb.
87. Oh NOW he loves her. I'm gonna strain my eyes from rolling them so much.
88. I am really not here for sexual predator assholes being redeemed. Which is actually the whole premise of this movie. Sigh.
89. OH MY GOD THE ESCALATOR SCENE!! NOW I’M CRYING! DAMMIT.
90. “I’m impressed.” “Well, I’m in love.” MY HEART.
91. This movie is sucking me right back in smdh.
92. They’re ~making love~ and Sebastian is asking if she’s okay and that’s character growth I guess.
93. Katherine is piiiiissed.
94. Ronald, you disappoint me.
95. “There’s some fucked up shit in this house.” You can say that again, Ronald.
96. “I wanna fuck.” Okay this is a great moment. It's still so rare to see a teen girl character show sexual agency and explicitly express sexual desire. It’s such a shame the treatment of Kathryn is as a total villain, meanwhile actual sexual predator Sebastian gets a redemption arc and dies a hero. Siiigh.
97. Sarah Michelle Gellar seems like she’s having such a great time in this role, though, and I love it.
98. Oh I forgot Sebastian dumps Annette because Kathryn manipulated him. Toxic masculinity, so fragile.
99. I love that Annette consistent calls him out. She's a great character.
100. I remember reading in TV Hits at the time that Ryan Phillippe vomited while filming this scene where Reese has to slap him. 13-year-old me thought that was so romantic.
101. Baby Reese Witherspoon is acting her little heart out. I adore her.
102. Sebastian is messy bitch who lives for drama.
103. This movie really reinforces the whore/virgin dichotomy and I’m so glad young me didn’t internalise too much of this crap.
104. How did Sebastian’s diary actually change Annette’s mind though? Like, surely it would put her off him even more.
105. Oh no they’re all converging in the middle of a busy New York street, I am STRESSED.
106. 13-year-old me is so emotional right now. And 31-year-old me also, a little bit. HE JUST FOUND LOVE AND IT CHANGED HIM. IT’S NOT FAAAAAAIR.
107. (Except like, fuck him, for real.)
108. How is this the first time Annette and Kathryn have ever met?
109. This bathroom scene is iconic, honestly.
110. HERE COMES “BITTERSWEET SYMPHONY”. YES.
111. “He’d want me to say, ‘Kathryn, I’m sorry’.” I’ve always wondered if Kathryn was meant to fuck up that line or if Sarah Michelle Gellar did it by accident.
112. The way this scene plays out is incredible. I mean, as an adult, I find the narrative really troubling. We’re supposed to feel triumphant that Kathryn finally gets her comeuppance. But it feels very out of character for Annette to do this? And I hate that Sebastian is a martyr while Kathryn is a demon. But, even recognising those problems, I still can’t help but enjoy the fuck out of it.
113. Aaand the movie comes full circle with Annette driving Sebastian’s car with his diary by her side, just as he drove it in the beginning.
114. How did she get his car though? Were his parents just like, “sure thing, we don’t know you, but take our dead son’s car”?
115. Well. Cruel Intentions has definitely not aged well. But I can see why I was so obsessed with it as a teen.
116. (It was all the sex.)
117. (And also the soundtrack.)
118. (But mostly the sex.)