* 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.
* FridgeLogic: 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.
* 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.
* TrueArtIsIncomprehensible: The Jester Theatre scene.
* 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.