Small Time Crooks (2000)
Film Overview
A hopeless former bank robber and his wife become unexpectedly wealthy when the cookie shop intended to disguise his latest criminal scheme becomes a spectacular success.
Woody Allen plays Ray Winkler, an ex-con working as a dishwasher and dreaming of one final big score. He persuades his wife Frenchy to use her savings to rent a shop near a bank, planning to tunnel from the basement into the vault.
Tracey Ullman plays Frenchy, who agrees to operate a cookie business in the shop as a front. While Ray, Denny, Tommy and Benny repeatedly lose their way underground, Frenchy’s cookies become so popular that the supposedly fake business rapidly becomes far more profitable than the robbery could ever have been.
Newly wealthy, Ray and Frenchy discover that having money creates a completely different set of problems. Frenchy becomes determined to acquire culture and social standing, while Ray finds himself increasingly uncomfortable with their new life.
Hugh Grant plays David, a sophisticated art dealer hired to educate Frenchy in painting, music, food and society. His attention encourages her growing conviction that she has outgrown Ray, although David’s interest in her is considerably less innocent than it appears.
Elaine May gives one of the film’s funniest performances as Frenchy’s cousin May, whose literal interpretation of almost everything said to her becomes an unexpectedly useful form of wisdom.
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My Review
The robbery that succeeds by failing
Small Time Crooks has one of those wonderfully simple comic premises that tells you almost everything you need to know about the characters: Ray Winkler devises a complicated bank robbery, while his wife accidentally makes millions selling cookies upstairs.
Ray is certain that crime is the path towards the life he wants. The joke is that the legitimate cover operation immediately proves more successful than anything he and his friends could achieve illegally. They cannot even tunnel in the correct direction.
Woody Allen plays Ray as a man with absolute confidence in abilities that have never produced much evidence of competence. He has been to prison, works as a dishwasher and remains convinced that the missing ingredient in his life is another criminal plan.
Frenchy understands him better than he understands himself. She knows the bank robbery is ridiculous, but years of marriage have apparently taught her that allowing Ray to discover this personally may be easier than attempting to explain it.
Ray spends weeks trying to break into a bank while Frenchy becomes rich selling cookies above his head.
Tracey Ullman is terrific because Frenchy changes enormously without ever becoming a completely different person. When the cookie business succeeds, the money does not merely allow her to buy expensive things. It gives her access to a world she had always assumed existed somewhere above her.
She wants paintings, music, fashionable friends and the confidence to enter rooms where she once imagined everybody would recognise that she did not belong. There is vanity in that, certainly, but there is also something understandable about wanting to discover what money has suddenly made available.
The problem is that Frenchy begins confusing culture with social approval. She does not simply want to learn about art because she likes it. She wants to become the kind of person who knows which art she is supposed to like.
Ray reacts in the opposite direction. The richer they become, the more he misses their old neighbourhood, familiar food and the uncomplicated version of their marriage that existed before anybody started talking about taste.
Frenchy thinks money will allow her to become somebody new. Ray discovers that money mostly makes him miss the person she already was.
Hugh Grant is perfectly cast as David because charm is his entire criminal method. He has none of Ray’s obvious roughness. He knows paintings, restaurants, manners and exactly which compliments Frenchy wants to hear.
The film’s title eventually applies to more people than Ray and his friends. They may be literal crooks, but their schemes are almost innocent beside the sophisticated people who understand how to separate wealthy newcomers from their money without ever looking vulgar.
David sees Frenchy’s insecurity immediately. He understands that flattering her taste is far more effective than openly flattering her wealth. She wants to believe she has acquired refinement, and he is willing to confirm that belief for as long as it remains useful.
The difference between Ray and David is therefore less moral than stylistic. Ray looks like a crook. David knows the correct fork.
Ray plans robberies in basements. David operates in galleries and restaurants. Only one of them has learned that good manners make theft look respectable.
Elaine May’s May is the film’s secret weapon. Her literal-mindedness creates some of the broadest jokes, but she also remains untouched by almost all the social anxiety consuming Frenchy.
May does not particularly care whether the room regards her as sophisticated. She listens to words, interprets them exactly as spoken and moves on. In a film full of characters performing versions of themselves for other people, that directness becomes oddly refreshing.
May also remains loyal to Ray when the rest of his life starts changing around him. Their conversations bring back the working-class comic world that the Winklers’ new wealth has temporarily displaced.
It is easy to see why Elaine May received so much critical attention for a comparatively small role. She never appears to be chasing the joke. The joke seems to arrive naturally whenever May tries to understand what everybody else is talking about.
Zhao Fei gives the film a warm, uncomplicated visual style that suits the broad comedy. After the period beauty of Sweet and Lowdown, this is contemporary New York photographed without the formal severity of Celebrity.
The locations are especially useful because the Winklers’ journey is partly geographical. Their original world of neighbourhood shops and ordinary streets gives way to larger apartments, fashionable restaurants and the cultural spaces Frenchy wants to inhabit.
Shea Stadium also becomes an ideal Ray location. Baseball and familiar pleasures make much more sense to him than the social education Frenchy has begun treating almost like a full-time profession.
The comedy works best when those worlds collide — when somebody who has recently become extremely wealthy discovers that wealth has not automatically supplied the vocabulary expected at the dinner table.
The Winklers acquire money overnight. Everything else the rich are supposed to know turns out to take rather longer.
The soundtrack plays with the same idea. With Plenty of Money and You is such an obvious choice that it becomes perfect, while Stompin’ at the Savoy, Harry James, Carmen Cavallaro and classical selections accompany the Winklers’ movement into wealth.
Johann Strauss and Rachmaninoff sit beside Tequila and older dance music, creating the musical equivalent of Frenchy’s attempt to absorb culture by surrounding herself with it.
The film never argues that culture itself is fraudulent. David genuinely knows more about art than Ray does. What it questions is the assumption that knowledge automatically makes somebody morally or intellectually superior.
Taste can be learned. Character remains another matter.
Inevitably, the money disappears. The cookie fortune is lost and the fashionable people attached to it vanish with remarkable efficiency. Frenchy discovers exactly how durable her new social identity was once the financial reason for maintaining it has gone.
Ray, meanwhile, has already begun understanding that the part of his life he wanted back was Frenchy rather than poverty itself. Their reconciliation is sentimental, but the film earns it because the marriage has always been more convincing than either character’s fantasy about money.
Frenchy then reveals one final surprise connected to a valuable necklace, suggesting that after spending the film surrounded by criminals and sophisticated opportunists she may have learned something useful after all.
Small Time Crooks is not trying to be a profound study of class, and that is part of its appeal. It is a fast, generous comedy built around the satisfying discovery that the most successful business plan in the film was the one nobody intended to succeed.
Ray wanted one big score. He eventually discovers that getting rich was much easier than knowing what to do once it happened.
Cast and Characters
Woody Allen
An ex-con and dishwasher who remains convinced that one properly planned bank robbery will finally transform his life.
Tracey Ullman
Ray’s wife, whose cookie business becomes enormously successful and opens the door to a wealthy social world she is determined to master.
Elaine May
Frenchy’s wonderfully literal-minded cousin, whose apparent simplicity often gives her a clearer view of events than the supposedly clever people around her.
Hugh Grant
A cultured art dealer hired to educate Frenchy who quickly recognises the financial opportunities created by her desire for sophistication.
Michael Rapaport
One of Ray’s criminal partners, equally enthusiastic about the bank scheme and equally incapable of making it work.
Jon Lovitz
Another member of Ray’s wonderfully ineffective criminal team, recruited for a robbery whose cover business quickly becomes the real source of money.
Money arrives to the sound of swing, standards and borrowed sophistication
The soundtrack moves from Hal Kemp and Benny Goodman to classical music, mirroring the Winklers’ sudden journey from neighbourhood life into a world of wealth and cultural aspiration.
With Plenty of Money and You
Hal Kemp and His Orchestra perform a song whose title captures the central fantasy of the film perfectly. Ray and Frenchy get the money; discovering what the “and you” part means proves rather more complicated.
A soundtrack climbing the social ladder with Frenchy
Benny Goodman, Harry James and Carmen Cavallaro bring familiar American swing and popular music into the film.
Johann Strauss, Rachmaninoff and Bach appear as Frenchy’s new life begins surrounding itself with the cultural markers of wealth.
Stompin’ at the Savoy
Goodman’s orchestra provides the kind of effortless swing Allen has repeatedly used to give New York comedy its rhythm.
Cocktails for Two
The elegant standard fits naturally into Frenchy’s increasingly elaborate social education.
Voices of Spring
The waltz belongs to the more formal musical world Frenchy begins embracing once money gives her access to it.
Tequila
A considerably less refined musical pleasure that feels much closer to the uncomplicated world Ray would happily return to.
Locations
Small Time Crooks stays firmly in New York, moving from neighbourhood streets to the more polished Manhattan world that opens up once the Winklers become wealthy.
Shea Stadium
The former home of the New York Mets appears as part of Ray’s more familiar and comfortable version of New York life.
Doyers Street
The distinctive curved Manhattan street was one of the real New York locations used during production.
Mott Street
Mott Street adds another recognisable downtown location to the film’s neighbourhood geography.
Riverbank State Park
The Hudson-side park was also used during the New York production.
Neighbourhood New York
The storefront and surrounding streets establish the ordinary world from which Ray and Frenchy’s completely unintended business empire grows.
Uptown Manhattan
Galleries, apartments and fashionable social spaces become the visual expression of the life Frenchy believes money should allow her to enter.
Awards and Recognition
Tracey Ullman Nomination
Ullman was nominated for Best Actress in a Motion Picture — Musical or Comedy for her performance as Frenchy.
Elaine May Wins
May won the National Society of Film Critics award for Best Supporting Actress.
Out of Competition
The film screened out of competition at the 57th Venice International Film Festival.
Tracey Ullman
Frenchy gives Ullman one of her richest film roles, moving from neighbourhood comedy to social ambition without losing the character’s warmth.
Elaine May
May’s understated delivery turns a supporting role into one of the film’s most memorable comic elements.
A Return to Broad Comedy
After the period jazz world of Sweet and Lowdown, Allen moved back towards the fast, plot-driven comic style associated with some of his earlier films.