History Film / BrewstersMillions1985

* MoneyToBurn: Defied. Rupert makes it clear Monty can't burn any of his assets, nor buy a bunch of Piccaso painting and use them for firewood, or he'll lose the challenge.

* AlumninumChristmasTrees: 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]].

* MoneyToBurn: Defied. Rupert makes it clear Monty can't burn any of his assets or he'll lose th challenge.

** The stamp store owner is a downplayed version of this: it is implied he is prejudiced against black men. When Monty enters his store, the security guard hovers around him and he automatically assumes Monty would be too poor to afford his products...until he learns Monty is ''the'' Montgomery Brewster who loves spending his money.

* {{Jerkass}}: JB Donaldo, the photographer. [[spoiler:When the rest of Brewster's staff puts up a collection to help keep Brewster from being completely broke, Donaldo is against donating any of his money, lying about not having his wallet with him and being forced into helping.]]

* GuileHero: Gradually, Monty manages to find ways to blow his money: from mailing an expensive rare stamp (destroying its value while still getting a service from it) and then buying an incredibly overpriced political campaign.

* MoneyToBurn: Defied. Rupert makes it clear Monty can't burn any of his assets.

* GuileHero: Gradually, Monty manages to find ways to blow his money: from mailing an overpriced stamp (destroying its value while still getting a service from it) and then buying an incredibly overpriced political campaign.

** Hilariously inverted when the mayoral candidates are so sick of Monty's MaliciousSlander, they sue the pants off of him, unaware that this would help this real goal.

* PlagueOfGoodFortune: This trope seems to kick in for Brewster right when he doesn't want it to. Every time he turns around, he either is getting helped by his friends who think his bad decisions are the result of a gambling and drinking habit, or he's winning at the failed stocks he throws his money behind.

* ReasonableAuthorityFigure: Edward Roundfield officially acts as an independent observer with no claim or stake in the bet. The law firm overseeing the will brings him in to make sure the will's details are carried out to the letter. He makes a point of being impartial, but in practice, he's clearly fond of Brewster and more sympathetic to his dilemma, since Brewster's a down-to-earth nice guy. He casually mentions that the deadline is midnight on the last day, then accepts the final receipt for the last $20,000 ''as the midnight chimes are ringing'' on the clock he'd earlier glanced at.

* DefrostingIceQueen: Angela Drake subverts this trope: she shows a softer side when Brewster begins to act more charitably, but her overall personality never truly changes, and she doesn't enter into a relationship with Brewster despite his best efforts.

* DidNotThinkThisThrough: Brewster is reminded that the office of Mayor comes with a substantial salary, and his newfound popularity may make him win even if he drops out.

* WhenTheClockStrikesTwelve: Two lawyers at the firm representing Brewster's great-uncle try to cheat Brewster out of his inheritance so they can earn a rather sizeable fee from the full $300 million before it's divided up to various charities. As time runs out on Brewster's chance to earn the inheritance, Angela informs Monty of the scheme. The resulting confrontating results in Monty completing the challenge and earning his inheritance--just as the clock finishes striking midnight.

** Brewster comes across at first as a working-class schmuck, a minor-league baseball player with little money or prospects. Brewster's Uncle Rupert states openly that he's disappointed in Brewster but has to name Brewster in the will because "I'm stuck with you." But as time goes on, Brewster finds more and more creative ways to waste money, from financing an expensive exhibition game, to buying a rare stamp and then ''mailing it,'' to buying a supply of expensive wine and then opening the bottles and serving them. When he has a serious setback and thinks he has no chance of making the deadline, he comes up with a perfect way to drain his bank account -- run for Mayor, spend through the roof on his campaign then purposely tank the election so he doesn't win and collect the salary that the job offers.

** Brewster comes across at first as a working-class schmuck, a minor-league baseball player with little money or prospects. Brewster's Uncle Rupert states openly that he's disappointed in Brewster but has to name Brewster in the will because "I'm stuck with you." But as time goes on, Brewster finds more and more creative ways to waste money, from financing an expensive exhibition game, to buying a rare stamp and then ''mailing it,'' to buying a supply of expensive wine and then opening the bottles and serving them. When he has a serious setback and thinks he has no chance of making the deadline, he comes up with a perfect way to drain his bank account -- run for Mayor and spend through the roof on his campaign.

** Spike has a somewhat savvy head for finance, and is able to become modestly wealthy himself with the salary that Brewster pays him. He also repeatedly tries to help Brewster tone down his carefree spending and help him invest it(unaware that it is the conditions of his inheritance).

* AmicableExes: Monty hires Walter and his interior decorator ex-wife to decorate an apartment, and the two tend to get along well.

As Monty starts hemorraging money as fast as he can, he soon realizes a horrible truth: [[SpringtimeForHitler it's amazingly difficult to lose an incredible amount of money]].[[note]]Well, under the conditions outlined in the will, anyway.[[/note]]

** Brewster comes across at first as a working-class schmuck, a minor-league baseball player with little money or prospects. Brewster's Uncle Rupert states openly that he's disappointed in Brewster but has to name Brewster in the will because, "I'm stuck with you." But as time goes on, Brewster finds more and more creative ways to waste money, from financing an expensive exhibition game to buying a rare stamp and then ''mailing it,'' to buying a supply of expensive wine and opening the bottles and serving them. When he has a serious setback and thinks he has no chance of making the deadline, he comes up with a perfect way to drain his bank account -- run for Mayor and spend through the roof on his campaign.

As Monty starts hemorraging money as fast as he can, he soon realizes a horrible truth: [[SpringtimeForHitler it's amazingly difficult to lose an incredible amount of money]].[[note]]Well, under the conditions outlined of the will, anyway.[[/note]]

* LettingHerHairDown: Angela does this.

* PlagueOfGoodFortune: This trope seems to kick in for Brewster right when he doesn't want it to.

* WhenTheClockStrikesTwelve: Two lawyers at the firm representing Brewster's great-uncle try to cheat Brewster out of his inheritance so they can earn a rather sizeable fee from the full $300 million before it's divided up to various charities. As time runs out on Brewster's chance to earn the inheritance, Angela informs Monty of the scheme. The resulting confrontating results in Monty completing the challenge and earning his inheritance--just as the clock strikes midnight.