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Irrational or Just a Small Time Crook?

SMALL TIME CROOKS, from left: Tracey Ullman, Woody Allen, 2000, © DreamWorks

It goes without saying – but we’ll say it anyway – that Woody Allen is one of the prolific directors in motion picture history. He’s written and directed a film virtually every year for well-over four decades. His most recent effort, Irrational Man, is his 46th film as writer-director. His most recent successes – including Match Point (2005), Midnight in Paris (2011) and Blue Jasmine (2013) – have been predominately dramas and without him in a featured role. This month’s Off-the Shelf choice is by no means among his great films. It is, however, arguably his last pure comedy and features what may well be the final memorable comedic turn of Woody Allen’s career.

In Small Time Crooks (2000), Woody Allen plays Ray Winkler, a lowly career criminal, who devises a plan with equally-inept cronies to rob a bank by tunneling from a leased building next door. Their cover is a newly-opened cookie shop run by Ray’s grating wife, Frenchy, played by Tracey Ullman. As expected, the robbery is a complete disaster… but the cookie business is an immediate success, leading to a multimillion dollar franchising operation for the Winklers.

Following the failed robbery plot and a slapstick tone in its first half, Small Time Crooks morphs into a satire of high society as the Winklers attempt to adjust to their newfound wealthy lifestyle. Their fortunes (literally) take another unexpected turn, after which Ray attempts one-last big score.


As usual, Woody Allen was able to attract a stellar supporting cast, including Hugh Grant, as well as Broadway stage legends Elaine Stritch and (in a very rare film role) Elaine May. Ray’s band of would-be thieves turned company executives includes characters played by Jon Lovitz and Michael Rapaport.

Elaine May’s film career was severely damaged as co-writer (with Warren Beatty) and director of 1987’s notorious failure, Ishtar.

In an unbilled role, Steve Kroft plays himself in a “60 Minutes” parody highlighting the successful cookie empire.

Despite multiple Oscar nominations over the years for Woody Allen films, Small Time Crooks was unjustly ignored by the Academy.

In a closing homage to the 1950’s sitcom classic, “The Honeymooners,” Ray embraces Frenchy and proclaims, “Baby, you are the greatest!”