If Woody Allen had stopped making movies right here, he’d still be a cult favorite just for this film’s absolutely bonkers absurdity. This is his first project as writer, director, and lead actor—not counting the overdub job on What’s Up, Tiger Lily?—and it’s so thin on narrative that it makes the old Marx Brothers movies look plot-heavy in comparison, but that’s okay. There are at least a dozen great belly laughs in this beautifully frivolous mock-documentary about the most inept career criminal on Earth. Great moments include the cello scene, the prison escape scene in which Allen sculpts a gun out of soap (a parody of an old story about John Dillinger), another prison escape scene where Allen runs away while attached to a bunch of other guys on a chain gang, and the two botched bank robbery scenes.
Allen originally approached Val Guest and then Jerry Lewis to direct his script (co-written with Mickey Rose), but neither of them worked out. He eventually decided to just direct it himself and got he got a small budget and full creative control from a new independent film company called Palomar Pictures.
In later years, Allen would return to the mock-documentary idea for Zelig and Husbands and Wives.