!!This movie contains examples of:
* AlternativeCharacterInterpretation: If you want to be more cynical about Bianca's HeelRealization, you could interpret her giving Cameron the BigDamnKiss as a convenient way to stop him from being mad at her. Or it could be genuinely wanting to make amends since a simple apology could be taken as manipulative. Or both.
* SugarWiki/AwesomeMusic:
** Jessica Riddle's "Even Angels Fall" playing during the prom as Kat walks away from Patrick.
** Letters to Cleo perform a very awesome cover of "I Want You To Want Me" over the end credits.
* CrossesTheLineTwice: Kat sneaking Patrick out of detention...by flashing the coach. The fact that this is a teenage girl doing so to an adult would normally raise eyebrows, but it's so hilarious that you don't care.
* DracoInLeatherPants: [=YouTube=] channel ''The Take'' framed Chastity as this. As detailed in both their [[https://www.youtube.com/watch?v=QQgmcQwbJew&ab_channel=TheTake "The Best Friend Trope, Explained"]] and [[https://www.youtube.com/watch?v=tmfG4OOh1v8&ab_channel=TheTake "The Becky Trope, Explained"]] videos, they paint her as a lonely girl who has to deal with AlwaysSomeoneBetter in comparison to Bianca (which is strictly head canon - Bianca is sought after because her father won't let her date). She's actually a FalseFriend who abandons Bianca at the party for Joey, laughs meanly at Cameron, and rubs it in Bianca's face that Joey only wanted her for the sake of a bet. She's arguably the closest thing the movie has to an AlphaBitch.
* EstrogenBrigade: With Joseph Gordon Levitt in the middle of his teen heartthrob phase, Andrew Keegan showing plenty of skin, and Heath Ledger's breakout role (and with a scene where he's walking around in tight leather pants) - it's unsurprising this ushered in puberty for many '90s/'00s girls.
* HilariousInHindsight:
** Kat reads books such as ''Literature/TheBellJar''. Creator/JuliaStiles was attached to play the protagonist in a film adaptation for years.
** Both Creator/HeathLedger and Creator/JosephGordonLevitt would go on to appear in ''Film/TheDarkKnightTrilogy''.
** A terrible sounding erotic novel written by a middle-aged woman? [[Literature/FiftyShadesOfGrey That will never happen in real life]].
** Kat apparently has a photo of Creator/JaredLeto in her room. Coupled with Creator/HeathLedger playing her love interest, she must have a thing for [[Film/SuicideSquad2016 the Joker.]] And ''Film/{{Joker 2019}}'''s SignatureScene is when the Joker dances on the stairs, and this film has a scene where Heath Ledger's character dances on stairs too.
** Watch ''{{Film/O}}'' right after this, which is another modernized Shakespeare play (in this case ''Theatre/{{Othello}}'') and stars Julia Stiles and Creator/AndrewKeegan. In both, [[spoiler: him not sleeping with her is a plot point]].
** 4 Years after this movie, Creator/GabrielleUnion would star in ''Deliver Us From Eva'', another adaptation of ''Theatre/TheTamingOfTheShrew'', but this time being the shrewish woman herself.
* JerkassWoobie: Kat seems like a straight-up {{Jerkass}} but she's dealing with her mother's departure, an overprotective father and [[spoiler: being dumped for not putting out]].
* MemeticMutation: Some fans of ''Series/TheWestWing'' make jokes about Mrs Perky really being CJ in a FallenOnHardTimesJob.
* NarmCharm: Patrick's singing "I Can't Take My Eyes Off Of You" to Kat during soccer practice. Cliched and silly yes, but damn if it works.
* OneSceneWonder:
** Creator/AllisonJanney as Ms Perky. Technically a Two Scene Wonder - but most of the fandom wishes she'd been in more.
** Mr Morgan, the CoolTeacher who takes no shit from Joey (or indeed Kat) has only about five minutes of screen time, but is another memorable part of the movie.
* RetroactiveRecognition: [[Film/TheDarkKnightTrilogy John Blake and the Joker]] went to high school together?
** If you're a scifi fan who can't put their finger on why Mr. Morgan looks and sounds so familiar, he was Tommy Webber in ''Film/GalaxyQuest'' around the same time.
* SignatureScene:
** The most memorable scene is the one where Kat reads out the titular poem, wells up with tears (an unscripted ThrowItIn from Julia Stiles), and runs out of the classroom.
** Closely followed by Patrick singing to Kat on the football field, one of the most iconic GrandRomanticGesture moments of the '90s.
* StrawmanHasAPoint: Walter gets annoyed at Kat when she drives into Joey's car after he blocks her way, and he has a point in that she intentionally damaged ''two'' cars that he's likely going to have to pay for, and his insurance won't cover actions like that.
* TearJerker:
** Kat discovering the bet is indeed quite a sobering moment, even if she's mostly snapping at Patrick. She believes he never cared about her and just saw her as a means to financial gain, while he's trying to convince her he does love her. She walks away, and you can then see Bianca appearing behind Patrick - feeling guilty for what her sister has just had to experience. Having "Even Angels Fall" playing over the scene doesn't help.
** The scene where Kat read the poem at the top of the main page in class. More specifically it was meant for Patrick. Kat starts to get tears in her eyes and cries as she's reading, and the camera goes to Patrick (Creator/HeathLedger) and you see he got kind of upset too. That would be because the script didn't call for tears, [[ThrowItIn but she actually started crying anyway]]. Most likely, that was also Heath's reaction to seeing her cry.
* TestosteroneBrigade: Larisa Oleynik playing a GirlyGirl whose beauty is displayed in every scene, and Julia Stiles showing off a more tomboyish yet still incredibly alluring persona (and some gorgeous long hair) and a beautiful young Gabrielle Union - male moviegoers had plenty to enjoy.
* UnintentionalPeriodPiece: The film would qualify only for the clothes and casual use of the word 'retarded', but Kat is also a huge fan of Creator/JaredLeto and other characters reference ''Series/TheRealWorld'' and ''Series/DawsonsCreek''. The original script had many references to the Washington Riot Grrl music scene that was big at the time, but the film does still name drop bands like The Raincoats and Bikini Kill. Letters to Cleo feature prominently - one year before they disbanded in 2000. The WildTeenParty comes about when invites are distributed via flyers instead of the internet, and Bianca and Cameron have to search Kat's room to find out what her interests are rather than just look at her social media. The poster for graduation even displays the slogan "Blasting into the year 2000".
* UnintentionallySympathetic:
** Despite the Stratford dad being cartoonishly overprotective, lines of dialogue say that the mother just up and left - and doesn't seem to be involved in their lives at all. As he's also a doctor, he's likely in over his head trying to raise two teenagers on his own. And let's face it - Kat is not the easiest girl to live with. [[spoiler: Mercifully he has a HeelFaceTurn by the end]].
** Patrick gets framed by the movie as having "embarrassed" Kat when he refused to kiss her after Bogey Lowenstein's party, and he's told by Cameron and Michael that he needs to make it up to her. However, at the time, ''Kat was drunk'' and was implied to not be in the right state of mind. As noted in ValuesDissonance, if Patrick had kissed Kat in that instance, it would be seen as him taking advantage of her. Patrick arguably did the responsible thing in that situation when he refused her advances and told her "Maybe we should do this another time." Even before this, he's the one who was telling Kat at the party to take it easy on the alcohol (which she ignored) and later helped her after she bumped her head on the chandelier because he was worried she might have gotten a concussion. It doesn't help tha Kat had already vomited that night, and pragmatically, Patrick perhaps just didn't want to kiss a girl whose breath smelled like puke. Played with in that their advice is less 'You did the wrong thing' and more 'She feels like she embarrassed herself in front of you, here's how to make her feel better' — it's contrived, but also understandable that a closed off person like Kat would withdraw when feeling exposed after embarrassing herself.
* ValuesDissonance:
** 'Retarded' is used casually by a couple of characters, as it was not widely considered a slur in the '90s.
** While scandalously hilarious, you'd probably not get away with a scene in which a teenage girl flashes her coach being PlayedForLaughs.
** It's also surprising that Kat gets annoyed at Patrick for ''not'' kissing her back while she's drunk. Her reasons are in fact more nuanced than QuestionableConsent but it's a surprising plot point all the same.
** While it's not entirely surprising that a sensitive guy like Cameron might be overly defensive about sounding gay, as it is generally sensitive guys who are labelled that way, with increasing awareness of how there is absolutely nothing wrong with being gay, his defensiveness can seem a little OTT by modern standards.
* ValuesResonance:
** It's been noted that the English teacher snapping at Kat is an early example of criticizing the idea of 'white feminism' focusing solely on the problems of privileged straight white women over people of color, disabled people, LGBT etc. This can also be applied to how [[https://www.teenvogue.com/story/standard-issues-white-supremacy-capitalism-influence-beauty Bianca]] [[https://www.npr.org/sections/codeswitch/2019/02/06/685506578/is-beauty-in-the-eyes-of-the-colonizer and]] Chastity are contrasted in terms of desirability within the story with the former only getting the Big Man on Campus ''only'' after the white Bianca is no longer available given how there is more serious attention to the [[https://gal-dem.com/if-you-exclusively-fancy-white-girls-thats-not-a-preference-thats-racist/ disparity in beauty standard preferences towards Black women]].
** Kat herself is a very layered character who subverts many tropes associated with {{Tomboy}}s or {{Straw Feminist}}s - especially for the time period. Years later, people still point to her as a relatably unconventional female lead. Likewise, Bianca is shown to be quite deep and layered while being completely different to her sister - [[RealWomenDontWearDresses with her femininity not being shown as a lesser trait]].
* TheWoobie: Cameron, particularly in the scene at the party when Bianca walks away from him...

!!The series contains examples of:
* BadassDecay: Patrick is initially ShroudedInMyth but later intimidates Cameron into accepting delivery of a Snuggy for him.
* EnsembleDarkhorse: Cameron and Bianca. The former due to being a LovableNerd and the latter to being much nicer than her movie counterpart.
* LesYay: Bianca and Dawn play this up in their webshow to get viewers. Walter is not pleased.
* HilariousInHindsight: Kat saying "I really did believe you kissed a girl and liked it" sounds funny after seeing Creator/LindseyShaw in ''Series/PrettyLittleLiars''.
* RetroactiveRecognition: [[Film/TheAmazingSpiderMan Flash Thompson]] as Joey!
* TheWoobie: Cameron and Bianca both alternate as this.
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