• Damian Masterson

Brewster’s Millions: 35th Anniversary




The 1985 film, Brewster’s Millions, begins with an opening scrawl that reads: “This is the story of Montgomery Brewster, a relief pitcher in the minor leagues of life, who got handed the American Dream...on a very hot plate.” This movie was an old favorite during my childhood. It does hold up in many ways, but having just recently rewatched it for the first time in twenty years, what I was most struck by was this framing of the story as a tale of the “American Dream.”


There is a fantastical element to the story of someone being plucked from obscurity for a grand adventure, but it says something that this depiction of the American Dream consists solely in the joy of winning and spending a great deal of money. Simply having money is the dream here, rather than building a fortune through work, or using a fortune to further some other noble end, or even using financial security to achieve other more fulfilling life goals. What was a little dispiriting to realize is that for many - both in the era the film was made and now - this film captures the American Dream exactly.



Richard Pryor plays Montgomery Brewster, an aging minor league ballplayer who learns that a previously unknown great uncle has left him a convoluted inheritance. Not unlike a game show, Brewster is made an offer by the executors of his great uncle’s estate. He has the option of pocketing a million dollars with no strings attached, or taking a chance to receive $300 million. The catch is that in order for Brewster to receive the $300 million, he will first have to squander $30 million in 30 days. There are restrictions on how Brewster can spend the money to insure that he wastes it, along with a requirement that he tells no one why he’s doing what he’s doing. By midnight of the last day of the month, Brewster needs to be completely penniless in order to win his full inheritance.


As a story, this is an old one. Based on the 1902 novel of the same name, this is the seventh American film adaptation of this story. There have also been 3 additional Indian film adaptations. From version to version, many of the details of the plot change, but the core of the story is always our protagonist having to fritter away a small fortune in order to win a much larger one, without being able to tell anyone why they are doing it. To have been adapted so many times, suggests there must be something deeply resonant to this premise, which is part of what I was troubled by on this rewatch.



Our Brewster accepts the challenge to win the $300 million quickly and easily - so easily that it makes one wonder at including a choice in the narrative at all. Ostensibly, the lesson Brewster is supposed to take from this experience, - stated explicitly by his great uncle in his video will - is to learn to value money through becoming sick of spending it. How seriously the film takes this lesson is hard to tell, as Brewster is never established as having any sort of pre-existing issue being irresponsible with money. The lesson is presented as a rationale for why the great uncle is issuing the challenge, but it’s never brought home in the course of the film as a lesson for Brewster or the audience to learn.


In one sense, Brewster’s real antagonist in the film is the clock: can he spend the money in the time allotted? The token opposition to him in that goal are the two lawyers at the law firm managing his great uncle’s estate. They want to see Brewster fail so they can retain control of the estate’s assets. In this effort they will enlist one of the junior lawyers at their firm, Warren Cox, to withhold some of Brewster’s money in order to surprise him at the last minute.


At the outset, Warren is briefly portrayed as an upstanding figure, engaged to be married to the equally upstanding accountant assigned to help Brewster manage his financial records, Angela Drake. Warren’s character may be the one in the film that has a true arc, in that he transitions from being a moral figure to becoming a willing criminal, though a goodly part of that transition happens before he’s even finished with his first scene - as he immediately compromises a stated principle against drinking alcohol when he is offered a five-inch thick stack of cash as a charitable donation from Brewster. Warren shows us something of the corrupting power of money, but it happens so quickly you might miss it.



Angela Drake’s job is to track Brewster’s expenses. Unbeknownst to her, the purpose of this is to verify that Brewster is complying with the stipulations of the will. Her role in the story is to be the virtuous figure, cajoling Brewster for not doing more good with his money, yet falling for him anyway despite his never actually doing anything especially good with his money.


Brewster is aided in his task by his personal catcher and only friend, Spike Nolan, played wonderfully by John Candy. As soon as Brewster comes out of the meeting where he learns of his inheritance, Brewster hires Spike at a massive salary to help him with his investments. The small character development that Spike has in the film is a move from enthusiastically supporting his friend’s spending, to trying to intervene before his friend fritters his inheritance away. Angela Davis, also slowly comes to help Brewster over the course of the film, proving to be instrumental in foiling Warren’s plot against Brewster at the last minute.


The central joke of the story is that Brewster takes great pains to squander his money, but keeps getting foiled by unexpected success. When he gambles, he hits on all his long shot bets and his seemingly terrible investments all happen to turn an immediate profit. He does manage to sink a bunch of money putting on a vanity exhibition game between his old minor league team and the NY Yankees. This digression is one of the actual moments of character development for Brewster, as he discovers and briefly has to contend with not being quite as good a pitcher as he believed himself to be.


The winning strategy Brewster finally hits on to most effectively waste his money is the most cynical part of the movie. Brewster decides to run for office, but as the office itself would count as an asset, he runs to lose with a nihilistic campaign to get ‘None of the Above’ elected mayor of NYC.



The premise of Brewster’s mayoral campaign is that both candidates are corrupt, so the voters should opt for ‘None of the Above’. But the film isn’t interested in whether either of the candidates actually are corrupt. It's just taken as a given that politicians are inherently corrupt and Brewster proceeds from that assumption. Our happy ending on this plot line is that Brewster successfully nullifies the election. It doesn’t take much imagination to draw the throughline from this kind of cynical thinking to many of the gravest problems of the modern world.


The conclusion of the movie comes quickly. Brewster learns that he was betrayed by Warren. He punches Warren, who threatens to sue Brewster for everything he’s about to not have. This gives Brewster the opening to use the remaining money Warren has surprised him with to retain Angela as his lawyer in any legal case Warren might bring, getting a receipt for legal services from her right as the clock strikes midnight. Brewster wins his full inheritance. He gets the girl - though it’s unclear why that happens; he punches out his rival, and then walks off screen with no indication that he’s grown or learned anything from the experience at all. Behold the American Dream!


Despite the tone of everything above, I find I still enjoy the film, but I feel a little bad about that. Director Walter Hill, recently coming off of his success on 48 Hours, keeps the story moving at a brisk and interesting pace. This is the only pure comedy that Hill ever directed, in an otherwise long career as an action film director, and fittingly for this film in particular, he readily admits he only did Brewster’s Millions for the money.


The casting of the movie is great. John Candy brightens every scene that he’s in. Stephen Collins brings more emotional range to Warren Cox than seems present on the page. And Richard Pryor is a true joy throughout the film. It is a genuine pleasure to see Pryor’s Montgomery Brewster succeed, with the shame of it being how hollow that success is upon examination.


Brewster’s Millions is worth revisiting. It’s well made and enjoyable throughout as a story. In terms of message, it is an interesting time capsule of American values in the 1980’s, as well as providing a reference point to the degree to which those same values of shallow consumerism still loom large in American culture today.





Damian Masterson


Damian is an endothermic vertebrate with a large four-chambered heart residing in New Windsor, NY with his wife and two children. His dream Jeopardy categories would be: They Might Be Giants, Berry Gordy’s The Last Dragon, 18th and 19th Century Ethical Theory, Moral Psychology, Caffeine, Gummy Candies, and Episode-by-Episode podcasts about TV shows that have been off the air for at least 10 years.


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