Pryor is Monty Brewster, an impoverished young man who inherits $30 million from a long-lost relative and also stands to further inherit $300 million. But the inheritance has a catch: to receive the $300 million, Monty must waste the entire $30 million in 30 days. He must end the challenge with no tangible assets whatsoever, with severe limits on possible outs like charity or purchasing items...and keep the arrangement a secret from everyone else. Monty wins the full inheritance if he pulls it off, but if he breaks any of the rules or fails to spend the $30 million in full, he gets nothing.
As Monty starts hemorrhaging money as fast as he can, he soon realizes a horrible truth: it's amazingly difficult to lose an incredible amount of money.note
John Candy plays Spike Nolan, Monty's best friend, and Lonette McKee plays Angela Drake, the paralegal assigned to accompany Monty and keep track of his spending.
This film contains examples of:
- Adaptational Villainy: In the original book, nobody tries to cheat Brewster out of the titular millions. In the film, the lawyers in charge of executing the will try to make Brewster lose the challenge so they can collect a fee for distributing the full inheritance to the charities chosen by Brewster's benefactor as alternative beneficiaries.
- All or Nothing: If Brewster fails the challenge, he gets nothing, and he has to give back whatever's left over of the $30 million.
- Amicable Exes: Monty hires Warren and his interior decorator ex-wife to decorate an apartment, and the two tend to get along well.
- Amoral Attorney: The lawyers in charge of executing the will are actively plotting to cheat Brewster out of his inheritance.
- Bail Equals Freedom: Subverted. Monty and Spike are arrested for a bar fight and given a choice between posting bail and showing up later for a trial or pleading guilty and paying a fine. If not for the lawyers looking for Brewster to inform him about an Unexpected Inheritance, they wouldn't be able to afford either option.
- Brick Joke: Monty is told that, after the thirty days, he can only have the clothes on his back or he loses the challenge. When the challenge ends, Brewster puts on the same baseball uniform he was wearing before the challenge started.
- Briefcase Full of Money: The first order Monty Brewster gives his newly hired head of security is for the man to go into the vault and collect $2 million in cash "for whatever expenses come up." The guard is later seen hauling around a single locked briefcase that he keeps handcuffed to his wrist.
- The Cameo: Rick Moranis puts in a brief appearance as "Morty King, King of the Mimics."
- Casual Sports Jersey: Exaggerated. When Monty is due to meet with the lawyers that control his deceased relative's inheritance in their boardroom, he wears his jersey and his cap.
- Composite Character: In the novel, Brewster has two benefactors: his grandfather, who leaves him the original small fortune with no strings attached, and his uncle, who leaves him the larger fortune on condition that he succeeds in the challenge to dispose of the smaller one. In the film, there's just one benefactor, Monty's great uncle Rupert Horn, and the small fortune is part of the challenge from the beginning.
- Consolation Prize: The will offers Brewster a million dollars with no strings attached, but as it's a "wimp" clause, he'd have to walk away from the challenge. If he accepts the challenge, it's All or Nothing, with no consolation prize.
- Defrosting Ice Queen: 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.
- Did Not Think This Through: 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.
- Eccentric Millionaire: Brewster's benefactor plays it straight, while Brewster himself merely invokes the trope, since he only appears to be extremely eccentric.
- Fat Best Friend: Spike.
- A Fool and His New Money Are Soon Parted: The challenge Brewster goes through for the full inheritance is meant as a lesson in how to avoid this trope.
- Gone Horribly Right: This is the case from Brewster's point of view when the hare-brained schemes he invests in end up succeeding.
- Hello, Attorney!: Angela Drake.
- Hidden Depths:
- 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.
- Most of Brewster's employees, save photographer JB Donaldo, avert being Fair Weather Friend by taking up a collection for him as they realize he's going bankrupt, which he must quickly find a carefully-worded way to refuse.
- Jerkass: JB Donaldo, the photographer. 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.
- Jerk With A Heartof Gold: Warren's ex wife Marilyn. While snobbish and haughty, she genuinely wants to decorate Monty's room to his liking and is saddened when he runs out of money and can't keep it.
- Just Between You and Me: Warren Cox spills the beans about the fix to Angela Drake in this manner; she then quickly informs Monty.
- Just for the Heli of It: Brewster flies his minor-league baseball team in on helicopters for a press event before an exhibition game between the team and the New York Yankees (which Brewster paid to make happen). The coach says the team will be tired after the trip—which was completely unnecessary because they're just over in New Jersey and could've gotten there faster on the bus—but Brewster says he did it to make an impression. (Of course he's not allowed to mention the real reason for taking the expensive option.)
- Letting Her Hair Down: When the movie begins, Angela is purely professional with her hair up, but near the end she sports a lady 'fro.
- Mythology Gag: If Monty chooses not to take the challenge, he walks away with one million dollars, the consolation prize specified in the "wimp" clause. In the novel, Brewster also has the option to decline the challenge and walk away with one million dollars, but in that case (minus eight decades of inflation) the one million dollars is the entire amount he was challenged to spend.
- Nice Job Fixing It, Villain!: The film features crooked lawyers who are trying to screw Brewster out of the deal. The junior partner of the firm, Warren Cox, "fixes" things twice: he informs Brewster's paralegal of the true nature of the inheritance (since Brewster isn't the one who tells her, the conditions of the will are not breached), then he threatens to sue after Brewster punches him in the face. Because the deadline had not yet been reached, Brewster hires his now-aware paralegal and uses all of the money that he had left over as a retainer fee. If Cox had just kept his mouth shut for a few more minutes, Brewster would have lost. (In addition, Cox was not supposed to have known about the deal, which meant Brewster would have won by default anyway.)
- Nice to the Waiter: Brewster's generosity earns him the admiration of his many employees, but this only means they want to help him when he starts going under.
- N-Word Privileges: In the Video Will, Brewster's white great-uncle snarks if Brewster is surprised his long lost relative was a honky.
- The Oner: The scene where Monty hysterically re-emerges from the office and everyone follows him into the elevator, and Spike's delayed reaction to news of the inheritance.
- On One Condition: And it's a doozy of a condition. A few smaller conditions come with it, but they're meant to prevent Loophole Abuse: Brewster can't have any assets after the challenge (except for anything he owned before it began); he can't tell anyone what he's doing or why; he must get value for the services of anyone he hires; he can only spend a predetermined small percentage on charities and gambling; and he can't buy expensive goods, then destroy them or give them away.
- Plague of Good Fortune: 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.
- Plot-Triggering Death
- Punctuated! For! Emphasis!: This is how Monty's great-uncle concludes the Video Will.Rupert Horn: [You] can go for the big one, Brewster. The three hundred million. But if you fail ... you don't. Get. DIDDLY!
- Race Against the Clock: This happens for most of the story, but it's openly invoked in the final scene as Angela writes a receipt for her services as a lawyer before the clock strikes midnight.
- Race Lift: Richard Pryor as Brewster, which leads to this line from Horn: "What's the matter? Didn't know your great-uncle was a honky?"
- Radish Cure: Giving someone millions of dollars and forcing them to spend it all within a short period of time might make them sick to the back teeth of both money and spending it. Monty's uncle, Rupert Horn, says he was given a Radish Cure by his father to discourage a possible smoking habit. Horn used this experience as motivation for creating Monty's challenge. And since nobody helped Rupert with the Radish Cure, he forces Brewster to avoid telling his friends about the condition (as they'd help Brewster win the challenge).
- Random Events Plot: The film follows a series of various humorous attempts to get rid of an exorbitant amount of money in a short amount of time.
- Reasonable Authority Figure: 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.
- Silly Will: Brewster inherits $30 million, 10% of the estate, and he must spend all of it within a month to get the remaining 90%. The hurdle is that he can't acquire assets, donate, or simply throw the money away, and nobody else may know what he's doing. He spends the movie hiring assistants, renting hotels, and baffling his friends who think money drove him insane.
- Springtime for Hitler: Brewster tries to blow a load of money by betting on longshots, but the longshots storm home and make him even more money. When he tries to lose money by investing in a worthless stock, the stock's value skyrockets after everyone else buys in. He tries to waste it on a frivolous political campaign, but the voters are attracted to his message and almost vote for him (which would have left him with a job and a salary, thus nullifying the inheritance), so Monty convinces people to vote for "None of the Above" and eventually drops out of the race.
- The Tape Knew You Would Say That: The editing in the video will scene makes it seem as if the two are sharing a direct back-and-forth dialogue.Rupert Horn: [in the video will] So, here's my proposition: you have thirty days in which to spend thirty million bucks. If you can do it, you get three hundred million!
Monty Brewster: [to himself] There's gotta be a catch.
Rupert Horn: Of course there's a catch!
- Unexpected Inheritance: The millions come from a relative he didn't even know before being informed of the inheritance.
- Unwanted Rescue: Since Brewster can't tell his friends why he's trying to lose money, they engage in well-meaning attempts to stem the flow by investing or saving it sensibly (much to Brewster's dismay).
- Video Wills: Brewster's great-uncle uses one to deliver his challenge.
- When the Clock Strikes Twelve: 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.
- Writers Cannot Do Math: This is excusable to make it easy for the audience. People around Brewster tell him repeatedly that he has wasted thirty million dollars when he has had at least ten million added onto that total. Saying "forty million" would be more accurate. But the audience is in on the bet, so the film avoids possible confusion by only using the "thirty million" number.