YMMV / Brewster's Millions (1985)

• Alternate Character Interpretation: 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 Upper-Class Twit?
• Aluminum Christmas Trees:
  • Among the many (unexpectedly successful) "investments" Monty makes is in a company that seeks to solve water shortages by towing icebergs to arid countries. Iceberg towing schemes have been around since the 19th century.
  • Rupert being locked in a closet until he finished cigars was an actual punishment for kids who smoked.
• Catharsis Factor:
  • 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.
• Harsher in Hindsight: Brewster's declaration, "You can get a [law] degree for $20,000!" is serious Black Comedy for anyone who's gone to law school since then.
• One-Scene Wonder: The legendary Hume Cronyn as Rupert Horn, Brewster's previously-unknown great uncle, makes quite the impression in his less than five minutes of screen time in the video will he left behind for Monty.
• Tear Jerker: While it's Played for Laughs, 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.
• Unintentional Period Piece:
  • A law firm without smartphones or computers is typical for the 1980s but kind of impossible in the 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.)
• Values Dissonance: 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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