Ray Winkler (Woody Allen), a small-time thief who has spent two years in prison, comes up with the "brilliant" idea of robbing a New York City bank by tunneling underneath it from a former pizza joint he has rented. The only obstacle is his yenta wife Frenchy (Tracey Ullman), who is against investing the $6,000 she's made doing nails into another one of her husband's crazy schemes. When she finally agrees, Ray and his three dim-witted partners (Michael Rapaport, Jon Lovitz, and Tony Darrow) make a mess of things by hitting a water pipe on their first day of drilling.
Writer and director Woody Allen returns to comedy in this clever film that makes the point that the biggest crime is not stealing something from others but pretending to be something you are not. Although Frenchy's cousin May (Elaine May) blows their robbery plans, it doesn't make any difference. Fate plays a dirty little trick on Ray and Frenchy by making them into multimillionaires. Her cookies, which she sells in the former pizza shop, become the latest rage in Manhattan. Soon Sunset Cookies has expanded into a wildly successful national franchise.
Frenchy, who once was an erotic dancer, decides to remake herself into a cultured person. But the art-and-opera crowd sees right through her. She then convinces David (Hugh Grant), a sophisticated art dealer, to teach her refinement. Meanwhile, the bored and restless Ray comes up with another moneymaking scheme once Frenchy jilts him.
The talented comedian Tracey Ullman carries this comedy with her élan and spunky contentiousness. Near the end, Frenchy abandons her upwardly mobile project and settles down into a more realistic assessment of her talents and gifts.