Guilty Pleasure No. 92: Brewster’s Millions (dir. by Walter Hill)

Posted on December 12, 2025 by Arleigh

Walter Hill’s Brewster’s Millions (1985) isn’t a perfect movie by any stretch, but it’s the kind of film that sneaks up on you. It may not be sharp enough to qualify as great satire or consistent enough to hit every comedic note, but it has an undeniable charm that pulls you in regardless. It’s loud, uneven, and often ridiculous, yet few comedies from the 1980s are as weirdly entertaining when they’re firing on all cylinders. For many movie fans, it’s that quintessential “guilty pleasure”—a film you know has problems, but that somehow feels impossible to turn off once it starts. And in many ways, that’s exactly where Brewster’s Millions finds its lasting appeal.

The setup alone is too fun to resist. Richard Pryor stars as Montgomery Brewster, a minor league baseball pitcher who unexpectedly inherits the opportunity of a lifetime—to claim a $300 million fortune from a distant relative. The catch? Before he can get it, he has to spend $30 million in 30 days under a bizarre set of conditions that make financial ruin easier said than done. He can’t give the money away, can’t destroy it, can’t buy assets or investments that retain value, and can’t tell anyone why he’s doing it. Fail, and he gets nothing. Succeed, and he becomes one of the richest men alive. It’s the sort of gleefully absurd premise that could only have come from Hollywood in the 1980s, and it’s immediately clear that the film wants audiences to sit back, grab some popcorn, and watch Pryor tear through cash in increasingly funny and desperate ways.

Richard Pryor is, without doubt, the heart and soul of the movie. He imbues Montgomery Brewster with equal parts manic energy and human frustration, giving the character a real emotional arc beneath all the comic spectacle. Pryor’s talent for blending humor with exasperation makes Brewster’s predicament believable, even when it’s insane. Watching him scramble to lose money while the world keeps rewarding him is strangely satisfying. Pryor understood how to play ordinary men caught in extraordinary circumstances, and that quality grounds the film when it could have easily spiraled into total silliness. In scenes where he loses his patience with accountants, schemes wild spending sprees, or watches his good intentions backfire, Pryor’s comic timing keeps the chaos enjoyable.

John Candy adds another layer of charm as Brewster’s best friend and teammate, Spike Nolan. Candy brings warmth, loyalty, and that unmistakable good-heartedness that made him one of the decade’s most beloved comedic actors. The chemistry between Pryor and Candy keeps the film buoyant even through its weaker stretches. Their friendship defines the film’s tone—it’s loose, goofy, and full of bro-ish camaraderie. Without Candy’s infectious energy, the movie’s more hollow comedic beats might have hit the floor with a thud. Together, they create a dynamic that feels real, even inside a premise that’s totally absurd.

As a director, Walter Hill feels like an odd fit for this kind of broad comedy, but that’s part of what makes Brewster’s Millions interesting. Hill, better known for tough, kinetic action films like The Warriors and 48 Hrs., approaches this farce with a surprising amount of structure and visual precision. The film looks slicker and sharper than most comedies of its kind, which gives the excess on-screen an unintentionally epic flair. Hill’s direction keeps the story moving, and though he’s not naturally a comedic filmmaker, his grounded style adds a peculiar edge to all the craziness. It’s chaos with discipline—an aesthetic that somehow works in the movie’s favor.

Still, Brewster’s Millions can’t quite escape its shortcomings. The pacing is uneven, especially in the middle, where the film loses some steam as Brewster cycles through increasingly repetitive spending gimmicks. The story flirts with satire but rarely commits, brushing up against deeper commentary on wealth, politics, and capitalism before retreating to the comfort of broad comedy. The “Vote None of the Above” subplot, where Brewster’s money-wasting political campaign taps into voter cynicism, is one of the smartest parts of the film—but it’s introduced and resolved too quickly to leave a mark. And while the movie is full of lively energy, not every gag lands; a few supporting performances veer into caricature, and some jokes feel very much of their time.

Yet these flaws are partly what make Brewster’s Millions such a delightful guilty pleasure. It’s the cinematic equivalent of junk food—high on calories, low on nutritional value, but deeply enjoyable all the same. Pryor’s constant exasperation, the sheer absurdity of trying to “waste” money legally, and the exaggerated set pieces (like the overblown parties or his failed attempts to lose at gambling) make for irresistible entertainment. Even when the humor dips into predictable territory, the concept keeps pulling you back in. There’s a giddy satisfaction in watching Brewster try—and fail—to lose money, especially because the universe just won’t let him.

The romance subplot with Lonette McKee’s character, Angela Drake, adds just enough heart to balance the absurdity. McKee gives a grounded, intelligent performance that prevents the love story from feeling tacked on, even if it never fully takes center stage. Her presence keeps Brewster tethered to some kind of reality, and the moral through-line—learning that not everything valuable can be bought—lands gently rather than preachily. It’s not profound, but it fits the breezy tone perfectly.

As a comedy of excess, Brewster’s Millions is very much a product of its time. The slick suits, the gaudy parties, the blind faith in wealth, and the Reagan-era optimism about money’s moral neutrality all ooze from every frame. That time-capsule quality is part of its modern appeal. Watching it today, you can’t help but smile at how on-the-nose it feels—a movie from the “greed is good” decade that accidentally ends up mocking the very mindset it sprang from. It’s self-aware only in flashes, but those flashes are enough to make you recognize the movie’s satirical edge hiding beneath its loud surface.

In the end, that’s what makes Brewster’s Millions endure as a lovable guilty pleasure. It has flaws you can’t ignore—uneven pacing, scattershot tone, underdeveloped ideas—but none of them outweigh its charm. Pryor’s comic genius makes even the weakest joke land better than it should. Candy’s warmth keeps the film light. And Hill’s straightforward direction infuses the lunacy with just enough realism to make it believable. The result is a movie that’s too silly to take seriously but too fun to dismiss. You watch it, laugh at its audacity, shake your head at the logic gaps, and yet somehow come away smiling.

Brewster’s Millions may not be a comedy classic, but it’s easy to see why people keep revisiting it. It’s comfort food cinema—lighthearted, clumsy, and endlessly watchable. And like all the best guilty pleasures, it doesn’t need to be perfect to make you happy. Sometimes, seeing Richard Pryor outsmart the meaning of money for two hours is more than enough.

Previous Guilty Pleasures

Retro Television Review: Miami Vice 3.2 “Stone’s War”

Posted on October 7, 2024 by Lisa Marie Bowman

Welcome to Retro Television Reviews, a feature where we review some of our favorite and least favorite shows of the past! On Mondays, I will be reviewing Miami Vice, which ran on NBC from 1984 to 1989. The entire show can be purchased on Prime!

This week, another friend of Sonny’s gets killed.

Episode 3.2 “Stone’s War”

(Dir by David Jackson, originally aired on October 3rd, 1986)

Sonny Crockett’s old friend, journalist Ira Stone (Bob Balaban), returns to Miami and he’s in trouble once again.

The last time we saw Stone, he appeared to be dying as the result of being severely wounded by Col. William Maynard (G. Gordon Liddy). I guess Stone survived because this episode opens with him and a cameraman in Nicaragua, filming anti-Communist rebels opening fire on a village. They even gun down a priest! However, it turns out that the rebels have got some help from some men who appear to be American. Stone’s cameraman is shot. Apparently leaving him to die, Stone grabs the tape of the attack and then flees to Miami.

In Miami, Stone tracks down Sonny, who is reluctant to get involved with Stone. However, when it becomes obvious that some agents of the government are not only following Stone but also trying to assassinate him, Crockett changes his mind. It turns out that the men in Nicaragua do indeed work for Col. Maynard. Maynard makes a return appearance, showing off a necklace of ears that have been chopped off of communists in an attempt to get businessmen to invest in his army. This episode drops some very obvious hints that Maynard is now working for the U.S. government.

In their efforts to help Stone get his tape to the public, Crockett and Tubbs get a few people killed. Local reporter Alica Mena (Lonette McKee) is murdered after Maynard’s men break into her office to search for the tape. In the end, Stone himself is once again wounded by Maynard’s man and this time, he actually dies on-camera. As for Maynard, he once again boards a private plane and escapes. The episode ends on a properly cynical note, with Crockett listening to reports blaming the death of the priest on the Nicaraguan government.

Actually, this whole episode feels a bit cynical. On the one hand, this episode criticizes the American government for being so anti-communist that it tries to overthrow the governments of other counties. On the other hand, a good deal of the episode’s running time is devoted to showing off Sonny’s new car, a 1986 Ferrari Testarossa. There’s even an extended chase scene that seems to exist largely so the show can work in as many close-ups of Sonny changing gears as possible. It’s a cool car but just try to get one in Nicaragua, Venezuela, or Cuba. (Or, I should say, try to get one without being related to someone who is in power.)

Ira Stone was a bit more compelling in his previous appearance on the show. In this episode, Balaban’s performance is almost too low-key. It lacks the manic instability of his first appearance, in which Stone was portrayed as being almost as mad as Maynard. This time out, he’s just another independent journalist who is convinced the government is out to get him. Fortunately, G. Gordon Liddy returns to Maynard and takes so much obvious joy in the role that he’s fun to watch. As I mentioned when Liddy last appeared on this episode, my father had a “G. Gordon Liddy for President” bumper sticker. As far as Watergate felons are concerned, Liddy was certainly less annoyingly self-righteous and more honest about his amorality than John Dean has turned out to be.

As a whole, this wasn’t a bad episode. Like last week’s episode, it was serviceable but it still seemed to be lacking the spark that distinguished the show’s first two seasons. For the second week in a row, Miami Vice puts more emphasis on its guest stars than the main cast and, perhaps as a result, the main cast seems to largely be going through the motions. (Zito and Gina don’t even appear in this episode. Castillo is barely present, which is interesting considering that the character is supposed to have connections in U.S. intelligence that would have perhaps been a bit helpful this time around.) Still, it was good to see both Stone and Maynard return to the show and remind the viewers that the vice in Miami is often the result of conflicts happening elsewhere.

A Movie A Day #264: The Cotton Club (1984, directed by Francis Ford Coppola)

Posted on September 29, 2017 by Jedadiah Leland

The time is the 1930s and the place is New York City. Everyone wants to get into the Cotton Club. Owned by British gangster Owney Madden (Bob Hoskins), the Cotton Club is a place where the stage is exclusively reserved for black performers and the audience is exclusively rich and white. Everyone from gangsters to film stars comes to the Cotton Club.

It is at the Cotton Club that Dixie Dwyer (Richard Gere) meets everyone from Dutch Shultz (James Remar) to Gloria Swanson (Diane Venora). Shultz hires Dixie to look after his girlfriend, Vera (Diane Lane). Swanson arranges for Dixie to become a movie star. Meanwhile, Dixie’s crazy brother, Vincent (Nicolas Cage), rises up through the New York underworld. Meanwhile, dancing brothers Sandman and Clay Williams (played by real-life brothers Gregory and Maurice Hines) are stars on stage but face discrimination off, at least until Harlem gangster Bumpy Rhodes (Laurence Fishburne) comes to their aid.

The Cotton Club was a dream project of the legendary producer, Robert Evans, who was looking to make a comeback after being famously charged with cocaine trafficking in 1980. Having commissioned a screenplay by his former Godfather collaborators, Mario Puzo and Francis Ford Coppola, Evans originally planned to direct the film himself. At the last minute, Evans changes his mind and asked Coppola to direct the film. After working with him on The Godfather, Coppola had sworn that he would never work with Evans again. (When he won an Oscar for The Godfather‘s screenplay, Coppola pointedly thanked everyone but Robert Evans.) However, by 1984, a series of box office flops had damaged Coppola’s standing in Hollywood. Needing the money, Coppola agreed to direct The Cotton Club.

Evans raised the film’s $58 million budget from a number of investors, including Roy Radin. Roy Radin was best known for putting together Vaudeville reunions in the 70s and being accused of raping an actress in 1980. Radin and Evans were introduced to each other by a drug dealer named Lanie Jacobs, who was hoping to remake herself as a film producer. During the production of The Cotton Club, Radin was murdered by a contract killer who was hired by Jacobs, who apparently felt that Radin was trying to muscle her out of the film production.

While all of this was going on, Coppola fell into his familiar pattern of going overbudget and falling behind schedule. This led to another investor filing a lawsuit against Orion Pictures and two other investors, claiming fraud and breach of contract. When the film was finally released, it received mixed reviews, struggled at the box office, and only received two Oscar nominations.

With all of the murder and drama that was occurring offscreen, it is not surprising that the film itself was overshadowed. The Cotton Club is a disjointed mix of gangster drama and big production numbers. As always with post-Apocalypse Now Coppola, there are flashes of brilliance in The Cotton Club. Some of the production numbers are impressive and visually, this movie has got style to burn. However, among the leads, neither Richard Gere nor Diane Lane seem to be invested in their characters while the talented Hines brothers are underused. The supporting cast is full of good character actors who are all in a search of a better script. A few do manage to make an impression: James Remar, Bob Hoskins and Fred Gwynne as veteran gangsters, Nicolas Cage as the film’s stand-in for Mad Dog Coll, and Joe Dallesandro as Lucky Luciano. The Cotton Club is sometimes boring and sometimes exciting but the onscreen story is never as interesting as what happened behind the scenes.