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* AcceptableTargets: The popular crowd are seen as shallow, vain and unworthy of any sympathy.
* CrowningMusicOfAwesome: "Kiss Me" by Music/SixpenceNoneTheRicher and EarWorm-worthy "The Rockefeller Skank" by Music/FatboySlim.
* DeaderThanDisco: Used to be a very popular film, but the end of the 90s and increasing parodization have reduced it to prime SnarkBait.
* HilariousInHindsight: Rachel Leigh Cook being in a LoveTriangle is amusing for ''VideoGame/FinalFantasyVII'' fans. She would later voice Tifa in the Compilation. Tifa is involved in one of the biggest love triangles still debated by fans to this day/
* HollywoodHomely: Granted, Zack's major concern was over Laney's personality, but a lot of emphasis is put on her physical makeover. WHO could possibly think Rachael Leigh Cook was unattractive? This has since become the most famous part of the movie, and an infamous example of this trope at work.
* IdiotBall: The third act has most of the characters grasping it for all its worth. Zack spends the prom with Taylor even though he has no interest in her whatsoever, and doesn't approach Laney due to obstacles that at most would require mild rudeness to overcome. When Jesse overhears Dean in the bathroom, instead of following him to Laney and then telling her, he runs to Mac, then both of them go to Zack, and even when they get to him, Mac waits about two whole minutes for Jesse to catch his breath instead of just telling Zack herself.
* IdiotPlot: Dean's [[SarcasmMode inspired]] choice for the bet. A girl who looks like Laney as opposed to people who weren't single, deeply unattractive or you know ''lesbian''. Any number of girls would have presented a greater challenge.
* NarmCharm: The BeautifulAllAlong moment is cliche and almost impossible to take seriously - due to rampant parodies and mocking on the internet. But damn if Rachel Leigh Cook's nervous grin as she reveals herself isn't endearing. And then she [[MomentKiller trips on her heels]].
* TrueArtIsIncomprehensible: The Jester Theatre scene.
* UnintentionalPeriodPiece: The movie is very obviously made in the 90s. Out of universe, it's yet another SettingUpdate of a classic work of literature following ''{{Film/Clueless}}'''s lead, and made during the period where teen high school comedies were all the rage. In-universe, Taylor dumps Zack for a guy famous for being on ''Series/TheRealWorld'', characters burst into spontaneous rap sequences and Creator/SarahMichelleGellar has a random cameo at the height of her popularity. Even the title and tag line ("hip, smart, hilarious") dates the movie to the 90s.
* UnintentionallyUnsympathetic: We never find out exactly why Laney is hated or considered unpopular, other than her father being the pool man. There's also a confrontation between Laney and Taylor at the party that implies some kind of bad blood between them, but it's the first time they interact in the movie. Laney just acts like a bitch to several people for no reason, and seems no nicer than the popular crowd.
* UnnecessaryMakeover: A famous example, going hand in hand with Hollywood Homely. While Rachel Leigh Cook does look nice after the makeover, the idea that she was in need of one is hard to take seriously. The girl who even helped her change {{lampshade|d}}s this by saying that she's "new, [[BeautifulAllAlong but not improved]]".
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