Small Time Crooks (2000)

Small Time Crooks is one of those comedies that feels like a perfectly timed joke that keeps finding new punchlines: a low-rent crime scheme collides with accidental, irresistible success, and the movie delights in watching its characters scramble to keep up. Woody Allen keeps the tone breezy and mischievous, but it’s Tracey Ullman who gives the film its heartbeat—sharp, buoyant, and genuinely funny in a way that makes the upward spiral feel both triumphant and precarious. The humor isn’t mean so much as slyly observant, poking at money, taste, and social climbing with the light touch of a caper and the bite of a satire. If you like your crime comedies more chatty and character-driven than action-packed, this is a charming, easy watch that reminds you how funny “getting what you want” can be.

Small Time Crooks is trying to be a light, old-school caper comedy that pivots into a “sudden wealth” satire, and you can feel Woody Allen aiming for breezy, accessible fun rather than anything deep. The problem is it often plays like a thin sketch stretched to feature length: the heist setup is the best hook, but once the cookie-business success takes over, the momentum softens and the laughs get more hit-or-miss. If you want a sharp, escalating crime comedy with clever twists, this may feel conventional and a bit inconsequential, like it’s coasting on a cute premise. Still, Tracey Ullman brings real energy, and if you’re in the mood for a mild, low-stakes comedy with gentle jabs at social climbing, it can be an easy watch.