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* ActorSharedBackground: Laura Allen attended Wellesley and graduated with a sociology major.

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* ActorSharedBackground: Laura Allen attended Wellesley and graduated with a sociology major. And after the film was criticised for its misrepresentation of the college and historical inaccuracies, she expressed regret about appearing in the film.



* WhatCouldHaveBeen: Chloe Sevigny was considered for the role of Giselle, but was reeling from the backlash of ''Film/TheBrownBunny'' - where she performed un-simulated fellatio on screen.

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* PlayingAgainstType: It was unusual at the time to have Kirsten Dunst play an AlphaBitch, though admittedly one who goes through CharacterDevelopment.
* RealLifeRelative: Julia Roberts was married to Daniel Moder, who was the film's second unit director. Dominic West felt quite awkward at filming love scenes with her while he was watching.
* WhatCouldHaveBeen: It was reported that Chloe Sevigny was considered turned down for the role of Giselle, but Giselle because she was reeling from the backlash of ''Film/TheBrownBunny'' - where ''Film/TheBrownBunny''. However, she performed un-simulated fellatio on screen.actually turned the role down in favour of that film, finding ''Mona Lisa Smile'' "faux feminist". She didn't regret her decision after the film's critical thrashing. Creator/MelanieLynskey also auditioned for that and the role of Connie.
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* RetroactiveRecognition: Creator/GinniferGoodwin has a small role as Connie in only her second film. Krysten Ritter - who would later achieve fame as the eponymous ''Series/JessicaJones2015'' - and Lily Rabe - of ''Series/AmericanHorrorStory'' fame - are extras in the art history class.
* WhatCouldHaveBeen: Chloe Sevigny was considered for the role of Giselle, but was reeling from the backlash of ''Film/TheBrownBunny'' - where she performed un-simulated fellatio on screen.

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* RetroactiveRecognition: Creator/GinniferGoodwin has a small role as Connie in only her second film. Krysten Ritter - who would later achieve fame as the eponymous ''Series/JessicaJones2015'' - and Lily Rabe - of ''Series/AmericanHorrorStory'' fame - are extras in the art history class.
* WhatCouldHaveBeen: Chloe Sevigny was considered for the role of Giselle, but was reeling from the backlash of ''Film/TheBrownBunny'' - where she performed un-simulated fellatio on screen.screen.
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** Julia Styles, a natural brunette, lightened her hair to blonde.

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** Julia Styles, Stiles, a natural brunette, lightened her hair to blonde.
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* RetroactiveRecognition: Creator/GinniferGoodwin has a small role as Connie in only her second film. Krysten Ritter - who would later achieve fame as the eponymous ''Series/JessicaJones'' - and Lily Rabe - of ''Series/AmericanHorrorStory'' fame - are extras in the art history class.

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* RetroactiveRecognition: Creator/GinniferGoodwin has a small role as Connie in only her second film. Krysten Ritter - who would later achieve fame as the eponymous ''Series/JessicaJones'' ''Series/JessicaJones2015'' - and Lily Rabe - of ''Series/AmericanHorrorStory'' fame - are extras in the art history class.
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* ActorSharedBackground: Laura Allen attended Wellesley and graduated with a sociology major.
* DyeingForYourArt:
** Kirsten Dunst, a natural blonde, darkened her hair to brown.
** Julia Styles, a natural brunette, lightened her hair to blonde.
* EnforcedMethodActing: All the actresses had to go through two weeks of finishing school to prepare for their roles.
* FakeAmerican: Like so many of his other roles, Dominic West is British playing an American.
* RetroactiveRecognition: Creator/GinniferGoodwin has a small role as Connie in only her second film. Krysten Ritter - who would later achieve fame as the eponymous ''Series/JessicaJones'' - and Lily Rabe - of ''Series/AmericanHorrorStory'' fame - are extras in the art history class.
* WhatCouldHaveBeen: Chloe Sevigny was considered for the role of Giselle, but was reeling from the backlash of ''Film/TheBrownBunny'' - where she performed un-simulated fellatio on screen.

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