A Fool and His Money (1989)

A Fool and His Money is the kind of scrappy, sly comedy that sneaks up on you: it starts as a romantic tale of ambition and insecurity, then sharpens into a surprisingly pointed satire about greed and the things people will believe if you sell them with enough confidence. Set against the hustle of New York and powered by the audacity of an ad man who treats life like a campaign pitch, it has an offbeat, inspired energy that keeps the laughs coming while quietly needling the culture of money-worship. George Plimpton’s presence adds a wonderfully wry credibility, the sort of performance that makes the absurd feel just plausible enough to sting. It’s not for everyone—its humor can be oddball and its edge a little mischievous—but if you like comedies that take big swings and have something to say beneath the grin, this one’s worth your time.

A Fool and His Money wants to be a scrappy New York rom-com satire about hustle culture, where a slick ad man chases a shady get-rich-quick scheme and risks the relationship he already has. The problem is it’s assembled with such weak acting, clunky dialogue, and bargain-basement production that the “comedy” often lands like dead air and the story barely feels like it’s moving. If you need a coherent plot, believable chemistry, or even basic polish, this will feel like a chore rather than a charming oddball discovery. The only real appeal is as a curiosity for bad-movie collectors who enjoy watching a sincere idea fall apart in real time.