* CastingGag: Creator/MalcolmMcDowell as Principal Gibbons. [=McDowell=]’s StarMakingRole in his native UK was in ''[[Film/{{If}} If….]]'', playing a non-conformist boys’ school student who with his friends stages an armed revolt against his school.
* CreatorBacklash:
** Amanda Bynes hated how her performance in the film turned out, and was part of the reason why she temporarily retired from acting.
** Emma Stone herself revealed that she's never watched the entire movie to this day, stating that it was an incredibly stressful project and that it brought up bad memories for her.
* DawsonCasting: All the high school kids, to the point that the joke about Micah being several years older than the others does not work since they all look the same age. Made more jarring since they managed to get actual 14-year-olds for the flashback sequence, making it look like the characters aged 10 years from 8th to 12th grade.
* PlayingAgainstType: The movie stars Creator/AlysonMichalka and [[Series/AllThat Amanda Bynes]] as mean girls. Both (especially Bynes) are more known for playing nice characters. [[Series/LizzieMcGuire Lalaine]] also has a cameo.
* RealLifeRelative: Emma Stone's brother is a prominent extra at the party where Olive "does" Brandon.
* StarMakingRole: Put Emma Stone on the map (though some credit could be given to ''Film/{{Zombieland}}'').
* TheCastShowoff: Creator/EmmaStone is definitely not a bad singer.
* WhatCouldHaveBeen:
** The movie was initially written as a hard-R adult comedy which featured, according to the writer Bert Royal, [[ClusterFBomb 47 F-bombs]]. This gives a little more credence to [[FelonyMisdemeanor Olive's response to Nina]], knowing that "twat" was probably originally a case of CountryMatters -- it would certainly make the principal's reaction a bit more justified.
** Emma Stone's audition, included as a special feature on the DVD and Blu-Ray releases, reveals that the original script had ''Brandon'' as the source of Olive's middle-school crush, and he was the boy that she lied about kissing during "Seven Minutes of Heaven."

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