Wednesdays with Woody: Small Time Crooks (2000)

Ex-con Ray Winkler (Woody Allen) convinces his wife, Frenchie (Tracy Ullman), to front a cookie store so that he and his friends can tunnel into and rob an adjacent bank. The store becomes a wildly successful business, and while the robbery attempt fails, the cookie empire – to their surprise – makes them millionaires.

The film’s cast is excellent, each performer bringing their own quirky incarnations of idiocy, however, the prizes go to the women. Tracey Ullman’s delivery is right on the mark, resting somewhere between Fran Fine and Carmela Soprano. Screenwriter Elaine May is superb as May Sloane, whose naïve honesty and daft delivery of exceptional dialogue seems to shame the ensemble of professional comedians. Allen discards his obsessive, neurotic New York intellectual, for a man of proudly flippant taste (though still obsessive and neurotic) interested exclusively in eating fast food and watching television.

The second act begins with a delightful documentary interview, in which we are re-introduced to the characters in their new roles within the Sunset Farm Corporation. Ray and Frenchie undergo lessons in life, taught by Hugh Grant (put to much better use than in Mickey Blue Eyes) as David, a young and debonair art-dealer for whom Frenchie develops a crush. As she begins to “outgrow” him, Ray forms a new bond with May and Allen showcases his beloved Manhattan through their budding friendship.

The final act sees Frenchie’s cookie crumbling, while Ray returns to crime, planning to replace a priceless emerald necklace with a fake. Ray and May make an hilarious crime duo, and their chemistry is somewhat better than his with Ullman.

The film largely addresses the different guises and fronts that people adopt and how the genuine article can become obscured and unattainable by farce. Ray failed as a stick-up man because his whole crew wore Ronal Reagan masks. The cookie store was a sham that became a legitimate success. David jokes that there is a portrait of him ageing in a closet somewhere. Ray spends half the heist reading his own map upside down. When given the opportunity to arrest them, a policeman decides to go into business with them instead.

Crooks operate within all circles of society. Being a successful crook, in itself, presents a moral contradiction, and as all criminality requires an element of fakery or disguise, it is easy to confuse your true self with that which you aspire to. Small Time Crooks is another hollowed-out American dream, redeemed by love, and its one of Allen’s funniest films.

Read more entries in our Wednesdays with Woody feature!

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