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* UnintentionalPeriodPiece: A law firm without smartphones or computers is typical for the 1980s but kind of impossible in the 2020s.

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* UnintentionalPeriodPiece: UnintentionalPeriodPiece:
**
A law firm without smartphones or computers is typical for the 1980s but kind of impossible in the 2020s. 2020s.
** Inflation would make it much, much easier for Brewster to spent $30 million dollars in the allotted time span today. (This is precisely why the challenge amount goes up every time the movie gets remade; in the original version, the challenge was to spend 1 million dollars ''in a year.'')

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* AluminumChristmasTrees: Among the many ([[SpringtimeForHitler unexpectedly successful]]) "investments" Monty makes is in a company that [[ZanyScheme seeks to solve water shortages by towing icebergs to arid countries]]. [[https://www.theatlantic.com/technology/archive/2011/08/the-many-failures-and-few-successes-of-zany-iceberg-towing-schemes/243364/ Iceberg towing schemes have been around since the 19th century]].

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* AluminumChristmasTrees: AluminumChristmasTrees:
**
Among the many ([[SpringtimeForHitler unexpectedly successful]]) "investments" Monty makes is in a company that [[ZanyScheme seeks to solve water shortages by towing icebergs to arid countries]]. [[https://www.theatlantic.com/technology/archive/2011/08/the-many-failures-and-few-successes-of-zany-iceberg-towing-schemes/243364/ Iceberg towing schemes have been around since the 19th century]].century]].
** Rupert being locked in a closet until he finished cigars was an actual punishment for kids who smoked.


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* ValuesDissonance: Even in the 1980s, Rupert's childhood punishment for smoking a cigar, being locked in a closet until he finished a whole batch, was seen as problematic. Nowadays, that kind of punishment would get Rupert's father ''at least'' a mandatory parenting course.
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* CatharsisFactor:
** Monty buying an overpriced stamp and then mailing it to Rupert's lawyers for being an incredible move by a working-class guy.
** Monty punching Warren over his deception, completing the challenge with Angela's help, and Edward immediately planning to sue Rupert's lawyers for fraud is oh-so-satisfying after all the trouble and pain Monty's had to go through.
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* TearJerker: While it's PlayedForLaughs, Monty has to make himself look like a reckless idiot in front of his friends to do the challenge, and he can't tell them why.

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* OneSceneWonder: The legendary Creator/HumeCronyn as Rupert Horn, Brewster's previously-unknown great uncle, makes quite the impression in his less than five minutes of screen time.

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* OneSceneWonder: The legendary Creator/HumeCronyn as Rupert Horn, Brewster's previously-unknown great uncle, makes quite the impression in his less than five minutes of screen time.time in the video will he left behind for Monty.
* UnintentionalPeriodPiece: A law firm without smartphones or computers is typical for the 1980s but kind of impossible in the 2020s.
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* AlternateCharacterInterpretation: Is Rupert trying to torment Monty with his challenge out of sheer contempt for Monty's lack of success? Or is he trying to prevent Monty from ending up like him: fabulously wealthy, but with no family or friends to share it with, in some Jacob Marley-esque warning from beyond the grave to not only care about getting more money?

to:

* AlternateCharacterInterpretation: Is Rupert trying to torment Monty with his challenge out of sheer contempt for Monty's lack of success? Or is he trying to prevent Monty from ending up like him: fabulously wealthy, but with no family or friends to share it with, in some Jacob Marley-esque warning from beyond the grave to not only care about getting more money? Or does he want to prevent Monty from being an UpperClassTwit?
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* FunnyAneurysmMoment: Brewster's declaration, "You can get a [law] degree for $20,000!" is serious BlackComedy for anyone who's gone to law school since then.

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* FunnyAneurysmMoment: HarsherInHindsight: Brewster's declaration, "You can get a [law] degree for $20,000!" is serious BlackComedy for anyone who's gone to law school since then.
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Added DiffLines:

* AluminumChristmasTrees: Among the many ([[SpringtimeForHitler unexpectedly successful]]) "investments" Monty makes is in a company that [[ZanyScheme seeks to solve water shortages by towing icebergs to arid countries]]. [[https://www.theatlantic.com/technology/archive/2011/08/the-many-failures-and-few-successes-of-zany-iceberg-towing-schemes/243364/ Iceberg towing schemes have been around since the 19th century]].
Is there an issue? Send a MessageReason:
None


* AlternateCharacterInterpretation: Is Rupert trying to torment Monty with his challenge out of sheer contempt for Monty's lack of success? Or is he trying to prevent Monty from ending up like him: fabulously wealthy, but with no family or friends to share it with, in some Jacob Marley-esque warning from being the grave not to only care about money?

to:

* AlternateCharacterInterpretation: Is Rupert trying to torment Monty with his challenge out of sheer contempt for Monty's lack of success? Or is he trying to prevent Monty from ending up like him: fabulously wealthy, but with no family or friends to share it with, in some Jacob Marley-esque warning from being beyond the grave to not to only care about getting more money?
Is there an issue? Send a MessageReason:
None


* AlternateCharacterInterpretation: Is Rupert trying to torment Monty with his challenge out of sheer contempt for Monty's lack of success? Or is he trying to prevent Monty from ending up like him: fabulously wealthy, but with no family or friends to share it with? And is part of that plan to make him so sick of money, he won't put it above things like personal relationships?

to:

* AlternateCharacterInterpretation: Is Rupert trying to torment Monty with his challenge out of sheer contempt for Monty's lack of success? Or is he trying to prevent Monty from ending up like him: fabulously wealthy, but with no family or friends to share it with? And is part of that plan with, in some Jacob Marley-esque warning from being the grave not to make him so sick of money, he won't put it above things like personal relationships?only care about money?
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* AlternateCharacterInterpretation: Is Rupert trying to torment Monty with his challenge out of sheer contempt for Monty's lack of success? Or is he trying to prevent Monty from ending up like him: fabulously wealthy, but with no family or friends to share it with? And is part of that plan to make him so sick of money, he won't put it above things like personal relationships?
Is there an issue? Send a MessageReason:
None

Added DiffLines:

* OneSceneWonder: The legendary Creator/HumeCronyn as Rupert Horn, Brewster's previously-unknown great uncle, makes quite the impression in his less than five minutes of screen time.
Is there an issue? Send a MessageReason:

Added DiffLines:

* FunnyAneurysmMoment: Brewster's declaration, "You can get a [law] degree for $20,000!" is serious BlackComedy for anyone who's gone to law school since then.
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