* ActorInspiredElement:
** Cher has a tic of constantly flipping her hair out of her eyes, which is something Alicia Silverstone does a lot herself.
** Creator/PaulRudd based Josh's activism and aborted attempt at growing a beard on his own college experiences.
* CastTheExpert: Creator/WallaceShawn has a small role as a debate teacher. He had been a teacher prior to acting.
* CastTheRunnerUp: Creator/PaulRudd auditioned for the roles of Murray, Christian and Elton. Rudd assumed that the character of Murray was a white teenager trying to act like a rapper.
* DawsonCasting: To varying degrees.
** Creator/BrittanyMurphy was 17, slightly older than her character Tai (15, turning 16), but she was still the only one who was actually in high school and because of her age, she required a parent or guardian with her during filming.
** Creator/AliciaSilverstone was 18, playing Cher at 15 to 16.
** The oldest among the "high school" cast was Creator/StaceyDash, who was 27 and playing someone more than a decade younger than herself. She was actually older than Creator/PaulRudd, who himself provided a case of this (he was 25 and playing someone who's 18 or 19).
* DuelingShows: Of a sort. The TV adaptation had something of a rivarly with ''Series/SabrinaTheTeenageWitch,'' with ABC having more faith in the former show and giving it more promotion, only for the show with the adolescent sorceress to turn out to be a SleeperHit. Notably, three actors from the TV show transitioned onto ''Sabrina'': Elisa Donovan, David Lascher, and Donald Faison.
* ExecutiveMeddling: Subverted. 20th Century Fox tried to reduce the amount of female characters, but Amy Heckerling put the project in turnaround, and Paramount picked it up.
* GenreRelaunch:
** The movie was arguably responsible for (at least temporarily) reviving the "Teen Movie" genre, after it had faded in relevancy during the first half of the '90s[[note]]''Film/DazedAndConfused'' notwithstanding[[/note]]. ''Film/CantHardlyWait'', ''Film/NeverBeenKissed'', ''Film/AmericanPie'', and more all more or less owe their existence to this movie.
** The film also popularized a short-lived, bizarrely specific trend of teen movies loosely adapted from classic literature and given a SettingUpdate to a contemporary high school. In ''Clueless''[='=] wake, ''Film/TenThingsIHateAboutYou'' is based on ''Theatre/TheTamingOfTheShrew''; ''Film/{{O}}'' is based on ''Theatre/{{Othello}}''; ''Film/ShesAllThat'' is based on Shaw's ''Theatre/{{Pygmalion}}''; ''Whatever It Takes'' is based on ''Theatre/CyranoDeBergerac''; ''Film/CruelIntentions'' is based on ''Literature/DangerousLiaisons''; ''Film/ShesTheMan'' is based on ''Theatre/TwelfthNight''; and of course, there's Creator/BazLuhrmann's [[Film/WilliamShakespearesRomeoAndJuliet adaptation]] of ''Theatre/RomeoAndJuliet''. ''Film/EasyA''[='=]s homages to ''Literature/TheScarletLetter'' could also be seen as a tribute to this sort of movies.
* IronyAsSheIsCast:
** Alicia Silverstone described herself as extremely anti-materialistic at the time, and wearing the same casual outfit to every audition - and found it a little surprising that she was cast as TheFashionista like Cher.
** Tai derisively calls Cher a "virgin who can't drive". At the time, Brittany Murphy really was a virgin who didn't know how to drive.
* MissingTrailerScene: Some of the trailers had a scene with Cher, Dionne, and Amber in the girl's room. While Amber is checking out her '50s style hairdo in the mirror, Cher asks, "Did I miss something? Is big hair back?" causing Dionne to mockingly laugh at Amber.
* TheOtherDarrin:
** Alicia Silverstone did not return for the tv series, leading to Cher being recast with Creator/RachelBlanchard.
** Mel Horowitz was recast twice, going from Creator/DanHedaya in the film to Creator/MichaelLerner in the first season of the show before Doug Sheehan took over for subsequent seasons.
** Josh, who only appeared in the first season, went from Creator/PaulRudd to David Lascher.
** Tai was recast from Creator/BrittanyMurphy to Heather Gottlieb before also being dropped after the first season.
* PlayingAgainstType: Alicia Silverstone had only done dramas before, and this was her first comedy.
* ProductionPosse: Amy Heckerling directed Alicia Silverstone and Wallace Shawn in ''Vamps'', and Stacy Dash and Paul Rudd in ''Film/ICouldNeverBeYourWoman''.
** Twink Caplan has appeared in every Amy Heckerling film since they first worked together on ''George Burns Comedy Week''. Caplan even played a teacher in Heckerling's ''Fast Times'', the TV show based on ''Film/FastTimesAtRidgemontHigh''.
* RealLifeWritesTheHairstyle: According to Creator/DonaldFaison, his character Murray gets his head shaved because [[PrematurelyBald his hair was already receding at 18]].
* RealLifeWritesThePlot:
** Breckin Meyer sprained his ankle rehearsing the half-pipe stunt, so many of his scenes had to be reworked to minimise his walking.
** The Mighty, Mighty Bosstones's performance was supposed to be outdoor, but had to be moved indoors because of heavy rain fall.
* RecycledTheSeries: ''Series/{{Clueless}}'', obviously.
* StarMakingRole: For Creator/AliciaSilverstone, Creator/PaulRudd, Creator/BrittanyMurphy, and Creator/BreckinMeyer.
* TechnologyMarchesOn: An odd example: Cher and her friends all have cell phones... which was meant to show how ridiculously ''wealthy and privileged they were''. Since nowadays every teenager regardless of social class has a cell phone, anyone watching the film today would simply comment on how dated the phones look. Likewise, the scene where the girls are [[ShortDistancePhoneCall talking to each other on the phone while walking side-by-side]] isn't quite so hilarious because, even if they're overwhelmingly texting each other rather than talking nowadays, it's entirely possible to see people doing this ''in real life''.
* ThrowItIn: Reportedly, Creator/AliciaSilverstone genuinely didn't know how to pronounce "Haitians", but the misread was so good that Amy Heckerling instructed her assistant director to discreetly inform the crew that if anyone corrected her, they'd be fired. One hopes that at least once the scene was completed she was informed.
* WhatCouldHaveBeen:
** The concept was originally to be developed as a TV pilot but, when Amy Heckerling switched agents, she was convinced to turn it into a film. What's more is that it wasn't originally planned as an ''{{Literature/Emma}}'' retelling; Amy just realised the similarities between Cher and Emma, and opted to make it a full-on SettingUpdate.
** Amy Heckerling met with Creator/AliciaWitt, Creator/ReeseWitherspoon, Creator/TiffaniThiessen, and Creator/KeriRussell for the role of Cher. Creator/AngelinaJolie and Creator/GwynethPaltrow were both considered for the role, but neither auditioned.
** Creator/BenAffleck and Creator/ZachBraff both auditioned for Josh.
** Creator/SethGreen and Creator/OwenWilson both auditioned for Travis.
** Creator/DaveChappelle and Creator/TerrenceHoward both auditioned for Murray.
** Creator/JeremyRenner auditioned for Christian.
** Music/LaurynHill auditioned for Dionne.
** Creator/SarahMichelleGellar was offered the role of Amber, but had to turn it down when ''Series/AllMyChildren'' refused to allow her time away, while Creator/ZooeyDeschanel was considered the role.
** Creator/JerryOrbach was offered the role of Mel Horowitz, but similarly could not get time away from ''Series/LawAndOrder'', while Creator/HarveyKeitel was deemed too expensive to be cast in the part.
* WorkingTitle: As Amy Heckerling is said to come up with a new title with each new draft, potential titles included ''No Worries'' and ''I Was A Teenage Teenager''.
* WriteWhatYouKnow: Amy Heckerling's grandparents had actually been step siblings, and she incorporated that into the Cher and Josh attraction.
* WriterRevolt: Amy Heckerling was told by 20th Century Fox that they wanted her to make something about "the in-crowd". She was sick of doing things about teenagers, so she only agreed with the intention of making fun of the culture.
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