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  • Accidental Aesop: Let a guy you barely know decide how you should look. You'll be happier.
  • Alternate Character Interpretation: It's often theorised that Laney was forced into the makeover. But since it happens almost entirely off-screen, you could be charitable and say that she and Mac worked together to pick a style that Mac approved of that Laney also wanted.
  • Angst? What Angst?: Off-screen in the third act, Dean was apparently coming on so strong to Laney, she had to use a fog horn to repel him. The whole thing is Played for Laughs and Laney doesn't seem bothered that she was nearly date raped.
  • Awesome Music: "Kiss Me" by Sixpence None the Richer and catchy "The Rockefeller Skank" by Fatboy Slim.
  • Harsher in Hindsight: A joke is made to the effect of "sexual harassment is still a big deal these days", and the film was produced by Miramax. Yikes.
  • Hilarious in Hindsight:
    • Rachael Leigh Cook being in a Love Triangle is amusing for Final Fantasy VII 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.
    • Roger Ebert heaped praise upon the unknown script doctor who worked on the movie, stating that their choice to add zingers into an otherwise pedestrian teen comedy kept his interest and made seeing the movie a worthwhile experience. The unnamed script doctor turned out to be M. Night Shyamalan, who ended up becoming one of Ebert's archenemies later in his career.
  • Hollywood Homely: 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.
  • Narm Charm: The Beautiful All Along moment is cliche and almost impossible to take seriously - due to rampant parodies and mocking on the internet. But damn if Rachael Leigh Cook's nervous grin as she reveals herself isn't endearing. And then she trips on her heels.
  • Never Live It Down: The film has never quite managed to shake off it's reputation for being the film that tried to convince everyone that Rachael Leigh Cook in glasses and with a slightly unflattering ponytail and wardrobe was somehow unattractive and in need of radical changes. Even now, it's still the first thing many bring up when talking about it, even in positive reviews and retrospectives.
  • Retroactive Recognition: Dean is Paul Walker before The Fast and the Furious.
  • Squick: Zack making two bullies who messed with Simon eat a pizza that they covered with pubes, complete with a closeup of the first bully biting into it and getting a hairy mouthful.
  • Took the Bad Film Seriously: The film is considered cookie-cutter 90s teen fluff, but Rachael Leigh Cook really does her best with the part of Laney and gives her lots of charm and has terrific chemistry with Freddie Prinze Jr. She makes some of the more problematic parts of the script and character work, or at least easier to accept. And her reaction upon discovering that Zack only took an interest in her to win a bet is genuinely heartbreaking.
  • Unintentional Period Piece: The movie is very obviously made in the 90s. Out of universe, it's yet another Setting Update of a classic work of literature following 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 The Real World, characters burst into spontaneous rap sequences and Sarah Michelle Gellar 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.
  • Unintentionally Unsympathetic: We never find out exactly why Laney is hated or considered unpopular, other than her father being the pool man and even then, she seems to live a comfortably middle-class life. 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.
  • Unnecessary Makeover: A famous example, going hand in hand with Hollywood Homely. While Rachael 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 lampshades this by saying that she's "new, but not improved".
  • Values Dissonance: The movie runs into this when trying to modernise Pygmalion. In the original text, Eliza's makeover is mainly about her behaviour rather than looks, and is heavily dependant on the class system - she's a poor Cockney girl who has to blend in with high society ladies. In a modern high school, Laney has Informed Poverty, is just as cute as the other girls and her unpopular status doesn't carry as much weight.
  • Values Resonance: The two goth girls who bully Laney, Misty and Savannah, are portrayed as unrepentant brats and aren't eventually shown to be any nicer or better than the more traditional mean girls. This arguably sends a message that anyone - even people who pride themselves on being outsiders - can be a bully. Given that they are nasty enough to tell Laney to kill herself, some viewers think they come off as even worse.
    • In a sense, the fact that Lainey is bullied and looked down upon despite being very attractive, coming from a fairly well-off background and not having any gripes with anyone shows that bullying isn't due to something a person does nor does it necessarily have a simple reason: Some people bully others for no other reason than that they are horrible.

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