Take the Money and Run (1969)

What makes Take the Money and Run special is how it turns the crime genre into a deadpan, faux-documentary playground where every “big break” collapses under the weight of one man’s spectacular incompetence. Woody Allen’s Virgil Starkwell isn’t a charming outlaw so much as a walking malfunction, and the movie finds endless, inventive ways to let his ambitions trip over spelling, timing, basic physics, and human nature. The vibe is breezy, absurd, and gag-rich, with a scrappy late-’60s energy that makes even the smallest moments feel like they’re in on the joke. If you like your comedy broad, eccentric, and relentlessly silly (rather than warm or sentimental), this is the kind of film that can win you over in the first five minutes and keep surprising you all the way through.

Take the Money and Run is Woody Allen aiming for a mock-documentary crime farce about a would-be outlaw who’s spectacularly bad at everything, and when it lands, it’s delightfully silly. The catch is it often plays like a string of comedy sketches taped together, so the pacing can feel ragged and the momentum comes and goes. If you like tightly plotted comedies or want a story that builds to something bigger, this may start to feel repetitive and a bit tiresome by the end. But if you’re happy to dip in for quick, clever gags and deadpan absurdity—especially Allen’s early, scrappy style—you’ll probably find enough laughs to justify the time.