It doesn't pay
Though it lacks the seriousness and the warmth of some of his best films, Small Time Crooks is the first Woody Allen film in roughly ten years to evince anything like a soul. It’s fun and funny, with a few perceptive moments and a hilarious performance by Elaine May.
The story, based on a Grimm’s fairy tale, is about a dorky, déclassé criminal couple who stumble on a fortune, only to be undone by the wife’s ambition. Ray Winkler (Allen) and his wife, Frenchy (Tracy Ullman), operate a cookie store as a front while Ray’s gang attempts to tunnel from the store’s basement to a bank vault two doors down. Everything falls through but the front: Frenchy, it turns out, bakes a mean cookie, and the store becomes a Starbucks-like overnight success. Ray and Frenchy get rich, but Frenchy, feeling inferior about her background, hires a rich jerk (Hugh Grant) to teach her how to be a cultured intellectual. Everything backfires. The moral of the story: be content with what ya got.
It may sound overly didactic or ironic-didactic; but we frequently forget the folksy charm of a good morality play, which Small Time Crooks is. Allen leavens the genre’s inherent predictability (we know as soon as she buys her first painting that Frenchy’s lust for class will come back on her) with jokes and diverting plot twists. Especially entertaining are Frenchy’s malapropisms and her disastrous taste in interior decor—old gags made new by Ullman’s comedic skill. Elaine May plays Frenchy’s batty sister and Tony Darrow, Michael Rapaport and John Lovitz offer able support as Ray’s cohorts. Allen gives himself one great scene, a moment of self-recognition, which seems like a sitcom equivalent of the moments of self-recognition in Sophoclean tragedy.