Ray (Woody Allen) and Frenchy (Tracey Ullman) are a married couple. Ray wants to lease an old restaurant with some friends of his so he can tunnel from the basement of the restaurant to a nearby bank.
Frenchy covers what they are doing by selling cookies from the restaurant. Ray hires the most inept crooks ever and the bank robbery scheme is a miserable failure. but selling cookies makes them millionaires. They even franchise the business.
Frenchy throws a big party and overhears people making fun of their decorating taste and lack of culture. She asks a man named David (Hugh Grant) to train her and Ray so they fit in society.
Ray hates every minute of it but Frenchy likes their new culture.
David is really just using Frenchy to get money for art projects he wants to do. Ray finally gets fed up and leaves Frenchy. David and Frenchy go to Europe for more cultural enlightenment and while there, she gets a call and finds out she's been defrauded by her accountants. She's lost everything including her cookie company, her home and possessions. David immediately dumps her.
Meanwhile, Ray has gone back to being a crook and tries to steal a valuable necklace at a party. He has had a duplicate made and through a series of circumstances gets the duplicate and real one mixed up. At the party he finds out that Frenchy is broke so he leaves and goes to see her. He consoles her by saying he stole the valuable necklace and shows it to her. Her new cultural enlightenment enabled her to tell the necklace was a fake. Ray had gotten the wrong one. But, she produced a cigarette case that she had given to David as a gift and stole back from him when he dumped her. It once belonged to the Duke of Windsor.
They reconcile and decide to sell it and go together to Florida.
Ullman was nominated for a Golden Globe for Best Performance by an Actress in a Motion Picture - Comedy/Musical for her performance and Elaine May won Best Supporting Actress at the National Society of Film Critics Awards for her performance.
Small Time Crooks was the highest grossing film directed by Allen at the North American box office between 1989's Crimes and Misdemeanors and 2005's Match Point with a gross of $17.2 million. However it was also one of the few later Allen films which did less well outside the U.S. and Canada, and its global gross was $29.9 million.
The plot of the film is very similar to 1942's Larceny, Inc. (the business in that film is a luggage store rather than a bakery), but Allen has never commented on whether there was a connection