History YMMV / CruelIntentions

* AdaptationDisplacement: The film has gone on to become much more famous and popular than [[Literature/DangerousLiaisons the 18th century novel]] it was originally based on. Even now, few people even know ''Cruel Intentions'' is just a modernized remake of an old French novel written centuries ago.

* HilariousInHindsight:
** Fans of Series/{{Buffy|The Vampire Slayer}} might be a bit disturbed at seeing the actress play a mega bitch, until we get to the final two seasons. Made better considering Creator/SarahMichelleGellar auditioned for the role of Cordelia initially, making this a window into what she could have done with that role instead.
** Kathryn laments that she has to act like "Mary Sunshine" all the time. Three years later, a supporting actress in this film, Christine Baranski, would play that part in ''{{Film/Chicago}}''.
** Creator/ReeseWitherspoon's boyfriend Trevor is said to be backpacking around Europe. Years later, [[Film/{{Wild}} Witherspoon goes on her own backpacking adventure.]]
** Annette and Cecile's relationship becomes funny when you consider they were rivals turned friends in ''Film/LegallyBlonde''

* EvilIsCool: Kathryn and Sebastian.

* EvilIsSexy: Surprisingly averted quite a bit. Kathryn is certainly more alluring and overtly sexualized than the NiceGirl Annette... but only at first and even then in private. She explains that she needs to seem pure and nonsexual in public, to keep her reputation and maintain her private affairs. Once Annette becomes sexually active, she's very open about her sexuality, which may be why she's more popular from then on.
* FanPreferredCouple: There are very few fanfics for the canonical pairing of Sebastian/Annette around the internet. Most fans were rooting for Sebastian to end up with his scheming stepsister [[EvilIsSexy Kathryn]], due to the main instigating force being them making the bet, which involves Kathryn letting him sleep with her, and Kathryn getting the DracoInLeatherPants treatment due to being played by Creator/SarahMichelleGellar.

** The ending of the film hinges on the audience accepting that Sebastian, though a bad person, redeemed himself [[spoiler:before his death]] and Kathryn receiving LaserGuidedKarma for her actions. However, while at the time it would be hard to argue she was any worse then him, nowadays with more reflection and better understanding of sexual consent and SlutShaming, Sebastian commits ''far'' worse crimes than she ever did (though she's a ManipulativeBitch, she never commits sexual assault, and Sebastian out-right seduces women ''solely'' to ruin their reputations), and his "redemption" amounts to realising he genuinely loves Annette, yet this love doesn't stop him continuing to still treat her terribly. With how he's a sexual predator who's only saving grace is a MoralityPet he kicks, while Kathryn is merely an AlphaBitch with a FreudianExcuse, he's still ''far'' worse than her, and anything she does to him would more come off as KickTheSonOfABitch. It comes off as BlackAndGrayMorality while expecting the audience sympathy to lie with the ''black'' side.

** As pointed out by WebVideo/NeedsMoreGay, the film was released in that weird transitory period where it's very hard to tell if the homophobic lines from certain characters are supposed to make them look bad, or are just something considered more acceptable at the time. Though, considering how the issue of LGBT rights wouldn't completely gain more traction until the early to mid 2000s, it's more likely that Sebastian's gay slurs were simply a reflection of the 1990s, an era where homosexuality was much less acceptable than it is now. Notably, despite regularly using homophobic slurs, he never actually seems to be against the idea of homosexuality, even congratulating Blaine at one point for having an active sex life.
*** Obviously, the gay slurs were used simply to emphasize the characters' viciousness and would definitely not have been considered acceptable language at the very least. (Just imagine Kathryn saying "Trevor's a fag" in front of anyone but Sebastian.) The only difference between now and then is that Sebastian might have less leverage with which to blackmail Greg in today's culture. It's fairly certain Sebastian couldn't care less that Greg was gay[[note]]He's obviously friends (or as much as he is with anyone) with the ''very'' out-of-the-closet Blaine[[/note]]; he simply found a weakness that he could easily exploit for his own gains.
** Similarly, Sebastian is supposed to be more sympathetic and likable than his literary counterpart, but that his act of sex toward Cecile ''still'' qualifies as rape, and that society has become more acknowledging of this in the past fifteen years.

** Mrs. Caldwell. Racist elitist snob or concerned mother who truly did want to protect her daughter and other young girls from being taken advantage of by cads like Sebastian and older men like Ronald? While not the most pleasant character in the film, she was actually the one who warned Annette about Sebastian's womanizing ways and regardless of etnia , just about ANY parent would be furious to see their teenage daughter being seduced by a music teacher. It didn't help Sebastian's case that until his HeelFaceTurn where he genuinely fell in love with Annette, he was every bit the manipulative bastard Mrs. Caldwell thought he was. It really didn't help Ronald's case that as Cecile's music teacher, he was very likely older than her, in addition to the fact that despite supposedly being in love with Cecile, Ronald really didn't seem to mind going bed-hopping with other girls like Kathryn.

** Sebastian first time taking advantage of the drunken Cecile. Sure it's PlayedForLaughs but many people with a mental disability have been taken advantage of in such a way by people they've trusted.

* StrawmanHasAPoint: The story narrative portrays Mrs. Caldwell as being in the wrong for standing against Ronald and Cecile being together and is mentioned a few times as being a bigoted racist. But even with all that, she wasn't wrong in saying she was the one who hired Ronald to be Cecile's music instructor (even if she did say it in a very tone-deaf and ignorant way). Thus as a parent, she had every right to be furious that the man she hired was trying to romance her daughter. And as an employer, she had every right to fire Ronald for what she personally saw as him taking advantage of her and breaking her trust. Considering some of Ronald's personal failings that get exposed later on (with him trying to sleep with Kathryn despite supposedly being in love with Cecile and being so hot headed that he [[spoiler: gets into a fight with Sebastian that ends in his death]]), Mrs. Caldwell can come off as being much more right than wrong in her stance to not let Ronald be around her daughter, even if she was doing it for wrong, narrow-minded reasons.

* AmbiguousDisorder: Cecile is implied to have some sort of mental disorder, coming from her immature behavior and childish style of clothing.
** It's implied that she's been overly sheltered, if anything.
*** Don't know that "overly sheltered" explains her having to be reminded that she needs to keep her legs closed while sitting down in a short skirt ... mentally she comes across as being about six years old.

*** Don't know that "overly sheltered" explains her not knowing that she needs to keep her legs closed while sitting down in a short skirt ... mentally she comes across as being about six years old.