Small Time Crooks is a 2000 American crime-comedy film written and directed by Woody Allen. It stars Allen, Hugh Grant, Elaine May and Tracey Ullman.
Small Time Crooks received positive reviews from critics. Ullman also received a nomination for a Golden Globe Award for Best Actress – Motion Picture Comedy or Musical, and May won the Best Supporting Actress citation at the National Society of Film Critics Awards.
Career criminal Ray (Woody Allen) and his cronies want to lease a closed pizzeria so they can dig a tunnel from the basement of the restaurant to a nearby bank. Ray's wife Frenchy (Tracey Ullman) covers what they are doing by selling cookies in the restaurant. The robbery scheme soon proves to be a miserable failure, but, after they franchise the business, selling cookies makes them millionaires.
In the film's second act, Frenchy throws a big party and overhears people making fun of their poor decorating taste and lack of culture. She asks an art dealer named David (Hugh Grant) to train her and Ray so they can fit in with the American upper class. Ray hates every minute of it, but Frenchy likes their new culture.
What Frenchy does not know is that David is really just using her to finance his art projects. 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 has been defrauded by her accountants. She's lost everything including her cookie company, home, and possessions. David turns on her right away and 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-found cultural enlightenment enables her to tell the necklace is a fake; Ray has gotten the wrong one. But she produces a very expensive cigarette case that she once had given to David as a gift but stole back after he dumped her. It once belonged to the Duke of Windsor. They reconcile, decide to sell it, and retire to Florida.Woody Allen as Ray Winkler
Tracey Ullman as Frances "Frenchy" Fox-Winkler
Elaine May as May Sloane
Elaine Stritch as Chi-Chi Velasquez Potter
Hugh Grant as David Perrette
Michael Rapaport as Denny Doyle
Tony Darrow as Tommy Walker
Jon Lovitz as Benjamin "Benny" Bukowski
Brian Markinson as Officer Ken DeLoach
George Grizzard as George Blint
Larry Pine as Charles Bailey
Kristine Nielsen as Emily Bailey
The film received generally positive reviews from critics. Review aggregator Rotten Tomatoes records that the film received 67% positive reviews, based on 99 reviews. Metacritic reports the film has an average score of 69 out of 100, based on 32 reviews.
Ullman was nominated for a Golden Globe Award for Best Actress – Motion Picture Musical or Comedy 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 film's plot is very similar to that of the 1942 comedy Larceny, Inc.. Allen has never commented on whether this was deliberate or if his film was in any way inspired by Larceny, Inc. The plot also parallels episodes of at least two American TV series: Gomer Pyle ("Dynamite Diner") and Car 54, Where Are You? ("The White Elephant").