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* RomanceOnTheSet:[[invoked]] She and Anthony Michael Hall dated during the ''Film/SixteenCandles'' and ''Film/TheBreakfastClub''.
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* RomanceOnTheSet:[[invoked]] She and Anthony Michael Hall dated during the productin of ''Film/SixteenCandles'' and ''Film/TheBreakfastClub''.
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* ''Series/TheBear'' (2022) as Al-Anon Moderator
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* ''Series/FeudCapoteVsTheSwans'' (2024) as Joanne Carson
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* ''Series/{{Riverdale}}'' (2017-present) as Mary Andrews
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* ''Series/{{Riverdale}}'' (2017-present) (2017-2023) as Mary Andrews
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Cool Loser TRS cleanup, has been renamed to Unconvincingly Unpopular Character and is a YMMV audience reaction.
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* PlayingAgainstType:[[invoked]] Although one of her most famous roles, Claire of ''Film/TheBreakfastClub'' was different for her; she had previously played {{Cool Loser}}s and weird girls. Conflicting stories even say that she was meant to play Alison because of this, but she herself affirms that she wanted to be Claire because she was different from her usual roles.
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* PlayingAgainstType:[[invoked]] Although one of her most famous roles, Claire of ''Film/TheBreakfastClub'' was different for her; she had previously played {{Cool Loser}}s and weird girls. Conflicting stories even say that she was meant to play Alison because of this, but she herself affirms that she wanted to be Claire because she was different from her usual roles.
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* ''Series/TheStand'' (1994) as Frannie Goldsmith
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* ''Series/TheStand'' ''Series/{{The Stand|1994}}'' (1994) as Frannie Goldsmith
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* DyeingForYourArt:[[invoked]] She dyed her famous red hair black for ''Series/TheStand''.
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* DyeingForYourArt:[[invoked]] She dyed her famous red hair black for ''Series/TheStand''.''Series/TheStand1994''.
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* LargeHam: Good God, '''YES.''' ''Film/ForKeeps'', ''Malicious'', and ''Series/TheStand'' are prime examples.
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* LargeHam: Good God, '''YES.''' ''Film/ForKeeps'', ''Malicious'', and ''Series/TheStand'' ''Series/TheStand1994'' are prime examples.
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* ''Series/SingleDrunkFemale'' (2023) as Alice
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** She turned down roles in movies that could have saved her mainstream career. Including: Molly in ''Ghost'', Kim in ''Film/EdwardScissorhands'', Claire in ''Film/DaysOfThunder'', Kit in ''Film/ALeagueOfTheirOwn'' and Dorothy in ''Film/JerryMaguire''.
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** She turned down roles in some movies that could have saved her mainstream career. Including: career; these include Sandy in ''Film/BlueVelvet'', Vivian in ''Film/PrettyWoman'', Claire in ''Film/DaysOfThunder'', Molly in ''Ghost'', ''Film/{{Ghost|1990}}'', Kim in ''Film/EdwardScissorhands'', Claire in ''Film/DaysOfThunder'', Kit in ''Film/ALeagueOfTheirOwn'' and ''Film/ALeagueOfTheirOwn'', Dorothy in ''Film/JerryMaguire''.''Film/JerryMaguire'', and Sidney in ''Film/{{Scream|1996}}''.
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* ''Series/DahmerMonsterTheJeffreyDahmerStory'' as Shari Dahmer
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* ''Series/DahmerMonsterTheJeffreyDahmerStory'' (2022) as Shari Dahmer
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* ''Series/DahmerMonsterTheJeffreyDahmerStory'' as Shari Dahmer
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* ActorInspiredElement:[[invoked]] She decorated Samantha's bedroom in ''Film/SixteenCandles'' with some items from her own home.
* CareerResurrection: For the longest time, she was the only actor included on the CondemnedByHistory page because of how far from grace she'd fallen since her TeenIdol days. However, appearing in ''{{Series/Riverdale}}'' (and eventually becoming a regular) and ''Film/TheKissingBooth'' brought her back to the mainstream and allowed her to enjoy a new image in her forties.
* DyeingForYourArt:[[invoked]] She dyed her famous red hair black for ''Series/TheStand''.
* TheMuse: John Hughes wrote ''Film/SixteenCandles'' and ''Film/PrettyInPink'' specifically for her. The former was written based only on her headshot, and the latter after she asked him to write a movie based on her favourite song.
* OldShame:[[invoked]] The TeenPregnancy film ''Film/ForKeeps'', widely considered to be her StarDerailingRole. She had hoped to make a film that showed the realities of teen pregnancy, but numerous CreativeDifferences resulted in something that she felt glamorized it.
--> "I feel like it glamorized teen pregnancy. And the original script that I'd agreed to do did not. But whenever you do a movie, whenever you do anything, it's a collaborative effort, and sometimes the script that you agree to do turns into something else. And I was pretty much a teenager at the time, and it was this runaway train that I didn’t know how to stop. And so I was very unhappy about that, and I felt like the movie was, I won’t say unfairly criticized, because I agreed. I really did feel like it glamorized teen pregnancy."
* PlayingAgainstType:[[invoked]] Although one of her most famous roles, Claire of ''Film/TheBreakfastClub'' was different for her; she had previously played {{Cool Loser}}s and weird girls. Conflicting stories even say that she was meant to play Alison because of this, but she herself affirms that she wanted to be Claire because she was different from her usual roles.
* RomanceOnTheSet:[[invoked]] She and Anthony Michael Hall dated during the ''Film/SixteenCandles'' and ''Film/TheBreakfastClub''.
* OldShame:[[invoked]] The TeenPregnancy film ''Film/ForKeeps'', widely considered to be her StarDerailingRole. She had hoped to make a film that showed the realities of teen pregnancy, but numerous CreativeDifferences resulted in something that she felt glamorized it.
--> "I feel like it glamorized teen pregnancy. And the original script that I'd agreed to do did not. But whenever you do a movie, whenever you do anything, it's a collaborative effort, and sometimes the script that you agree to do turns into something else. And I was pretty much a teenager at the time, and it was this runaway train that I didn’t know how to stop. And so I was very unhappy about that, and I felt like the movie was, I won’t say unfairly criticized, because I agreed. I really did feel like it glamorized teen pregnancy."
* PlayingAgainstType:[[invoked]] Although one of her most famous roles, Claire of ''Film/TheBreakfastClub'' was different for her; she had previously played {{Cool Loser}}s and weird girls. Conflicting stories even say that she was meant to play Alison because of this, but she herself affirms that she wanted to be Claire because she was different from her usual roles.
* RomanceOnTheSet:[[invoked]] She and Anthony Michael Hall dated during the ''Film/SixteenCandles'' and ''Film/TheBreakfastClub''.
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* WhatCouldHaveBeen: She turned down roles in movies that could have saved her mainstream career. Including: Molly in ''Ghost'', Kim in ''Film/EdwardScissorhands'', Claire in ''Film/DaysOfThunder'', Kit in ''Film/ALeagueOfTheirOwn'' and Dorothy in ''Film/JerryMaguire''.
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* WhatCouldHaveBeen: WagTheDirector:[[invoked]]
** In ''Film/TheBreakfastClub'', only Claire was supposed to dance, but Molly felt uncomfortable dancing in front of everyone. So John Hughes had the other characters dance too. Ironically she later felt this hurt the movie, finding the group dance to be overly choreographed.
** She insisted on wearing the hat at the beginning of ''Film/SixteenCandles'', against the wishes of the costume designer. After the movie's success, it became a fashion trend among young women.
* WhatCouldHaveBeen:
** She turned down roles in movies that could have saved her mainstream career. Including: Molly in ''Ghost'', Kim in ''Film/EdwardScissorhands'', Claire in ''Film/DaysOfThunder'', Kit in ''Film/ALeagueOfTheirOwn'' and Dorothy in''Film/JerryMaguire''.''Film/JerryMaguire''.
** She also expressed interest in doing sequels to ''Film/SixteenCandles'', but turned many of them down. In 2005, she mentioned being impressed with one titled '32 Candles', and wished that one could have been made.
** In ''Film/TheBreakfastClub'', only Claire was supposed to dance, but Molly felt uncomfortable dancing in front of everyone. So John Hughes had the other characters dance too. Ironically she later felt this hurt the movie, finding the group dance to be overly choreographed.
** She insisted on wearing the hat at the beginning of ''Film/SixteenCandles'', against the wishes of the costume designer. After the movie's success, it became a fashion trend among young women.
* WhatCouldHaveBeen:
** She turned down roles in movies that could have saved her mainstream career. Including: Molly in ''Ghost'', Kim in ''Film/EdwardScissorhands'', Claire in ''Film/DaysOfThunder'', Kit in ''Film/ALeagueOfTheirOwn'' and Dorothy in
** She also expressed interest in doing sequels to ''Film/SixteenCandles'', but turned many of them down. In 2005, she mentioned being impressed with one titled '32 Candles', and wished that one could have been made.
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* ''Film/TheKissingBooth'' (2018) as June Flynn
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* ''The Kissing Booth'' series as June Flynn
** ''Film/TheKissingBooth''(2018) as June Flynn(2018)
** ''Film/TheKissingBooth2'' (2020)
** ''Film/TheKissingBooth3'' (2021)
** ''Film/TheKissingBooth''
** ''Film/TheKissingBooth2'' (2020)
** ''Film/TheKissingBooth3'' (2021)
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* ''Film/TheKissingBooth2'' (2020)
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* TrademarkFavoriteFood[=/=]BizarreTasteInFood: Famous during the Creator/BratPack years for going to at all the trendiest restaurants and ordering onion rings with the onions removed.
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* TrademarkFavoriteFood[=/=]BizarreTasteInFood: Famous during Onion rings drenched in ketchup. Not so unusual at first thought, but what would make it odd was that she would ask that the onions be removed after the onion rings came out of the fryer. During the Creator/BratPack years for going to years, she would order this at all the trendiest restaurants and ordering onion rings with restaurants, some of which took to calling it the onions removed."Ringwald Special."
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* ''Film/JemAndTheHolograms'' (2015) as Aunt Bailey
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* ''Film/JemAndTheHolograms'' ''Film/JemAndTheHolograms2015'' (2015) as Aunt Bailey
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* WhatCouldHaveBeen: She turned down roles in movies that could have saved her mainstream career. Including: Molly in ''Ghost'', Kim in ''Film/EdwardScissorhands'', Claire in ''Film/DaysOfThunder'', Kit in ''Film/ALeagueOfTheirOwn'' and Dorothy in ''Film/JerryMaguire''.