Film
A Fool and His Money
- Comedy
- Light-hearted
A scrappy 1989 romantic comedy about a fired advertising executive who pivots to peddling a dubious product, with Sandra Bullock as his conscience-stricken girlfriend. It's buoyant and silly, the kind of film that swings for the fences with its satire but doesn't always connect. Made for people who like their romance tangled up with commerce and chaos.
Should you watch it?
Watch it if you enjoy satirical comedies about hucksters and ad-world cynicism, where a scheme gets sillier as it goes and the jokes land with a perfectly straight face.
Skip it if you need a romance to carry the film, because the love story stays thin while the satire and the stunts take most of the running time.
What it asks of you: It runs 81 minutes and moves in quick, broad bursts, so it asks you to go along with its cartoonish logic rather than settle in for slow character work.
Not sure? Find tonight's pick in a minute.
If you liked this
Working Girl1988
Melanie Griffith climbs the corporate ladder with charm and gumption in a film that celebrates ambition while poking fun at Wall Street excess. Sharper writing and stronger performances than you'd expect from a date-movie premise.
But The gender politics, though well-intentioned for 1988, feel dated now, and the film's endorsement of the system it critiques is ultimately soft.
Baby Boom1987
Diane Keaton ditches her Manhattan career for a small-town business venture. It's sweet and funny without being cloying, and genuinely interested in what happens when ambition recalibrates.
But The fantasy of escape-to-the-country is never complicated, and the film's resolution is almost aggressively tidy.
Eating Raoul1982
A deadpan satire about a straight-laced couple who discover there's money in murder. Paul Bartel's direction is wickedly precise, and the premise never overstays its welcome in 87 minutes.
But It's very dark, and the humour is surgical rather than warm—some will find it chilly rather than clever.
Not sure tonight? Get a pick in a minute, starting from A Fool and His Money
The wildcard
Something you would not have found on your own.
The Wolf of Wall Street2013
Both follow a man's moral compromise in pursuit of wealth, but where A Fool finds redemption through love, Wolf of Wall Street suggests there is no redemption—only the next high.
Scorsese's three-hour rager about a man whose hunger for money consumes everything—family, love, sanity. It's where A Fool and His Money's premise goes if you pull the thread without mercy. Funny and horrifying in equal measure.
But It's graphically violent, sexually explicit, and morally ugly. The film asks you to watch depravity without flinching or looking away.
More like this (8)
Ghostbusters II1989
Released the same year, it's equally goofy about capitalism and ambition, with Bill Murray delivering wisecracks about money and meaning. A comfort watch with genuine laughs.
But It retreads the first film's formula pretty heavily, and the supernatural plot is less interesting than the characters.
Do the Right Thing1989
Also from 1989, Spike Lee's film wrestles with commerce, community, and morality with a force and urgency that make it unforgettable. The heat in this one is real.
But It's a tragedy, not a comedy—devastating and unresolved. A different beast entirely, and the tonal shift may feel jarring if you're seeking lightness.
After Hours1985
Scorsese's fever dream of a film about a computer programmer's night spiraling into chaos. It's agile, surreal, and funny in ways that feel dangerous—closer to the energy of a scrappy satire.
But It's deliberately disorienting and cruel to its protagonist. The humour comes from genuine peril, which isn't for everyone.
Desperately Seeking Susan1985
Madonna and Rosanna Arquette in a fizzy caper about identity and reinvention. It moves fast, looks great, and finds real humanity underneath the high-concept premise.
But Madonna's acting is uneven, and the plot relies on coincidences that strain credibility even by '80s rom-com standards.
Splash1984
Tom Hanks and Daryl Hannah in a romantic comedy that actually earns its emotional beats. It's silly and touching without feeling manipulative—a genuine pleasure.
But The fantasy premise, while charming, doesn't leave much room for the kind of satirical bite that drives A Fool and His Money.
Troop Beverly Hills1989
Shelley Long as a wealthy woman learning life lessons through Girl Scouts. It's earnest and goofy in equal measure, and surprisingly warm-hearted about its satire of privilege.
But The humor is broad, the message is blunt, and it asks almost nothing of the audience intellectually.
The Pitch2012
Where A Fool and His Money treats the advertising hustle as a romantic comedy backdrop, The Pitch makes the pitch itself the whole story—what it looks like when people will sell anything.
A British mockumentary following desperate entrepreneurs pitching absurd products to investors. It captures the same energy of self-delusion and scrambling hustle, but with documentary precision that makes the satire even sharper.
But It's quietly uncomfortable rather than traditionally funny. The humor lives in the awkwardness, and it won't spell out the punchlines for you.
Synecdoche, New York2008
Both films are about a man's ambition derailing his relationship with a woman who loves him, but Kaufman strips away the rom-com machinery to show what that actually costs.
Philip Seymour Hoffman as a theater director whose ambition to create an art-world empire collapses his marriage and sanity. Charlie Kaufman's film is strange, exacting, and devastating—about how the pursuit of meaning can destroy the life you already have.
But It's deliberately obscure, three hours long, and offers no catharsis. If you want to feel better at the end, this is not the film for you.
People
Cast
Sandra BullockDebby Cosgrove
Jerzy KosińskiBettler
Jonathan PennerMorris Codman
George PlimptonGott- Gerald OrangeIan Clarity
- José TorresHimself
Directing
- Daniel AdamsDirector
Writing
- Daniel AdamsWriter
- Michael MailerWriter