Exploring the filmography of Woody Allen is always a fascinating endeavour, and the further we go back in his career, the more we see how he’s changed as a filmmaker. Whether or not his change in style is indicative of growth or regression depends on how one feels about these different stages of his career. His first real directorial effort (in terms of containing original footage), Take the Money and Run, would be the film that defined most of the upcoming decade in terms of featuring Allen’s more abstract, high-concept approach to comedy, where the director is making exceptionally strange films that lay off the beaten track, often presenting scathing commentary on form, flourishing into the kind of humour we take for granted nowadays. Perhaps not a film that sees Allen at his creative peak, and rather one that sees him still developing his filmmaking capacities, his work in this film is certainly undeniably memorable, with his outlook on the subject, and his provocative approach to the craft already showing that Allen possessed an incredible prowess for filmmaking, long before he became as revered a filmmaker as he would in subsequent decades. Jagged in style, rough in storyline but still featuring traces of brilliance, Take the Money and Run is exactly what we’d expect from a filmmaker who, at this point, was still testing the cinematic waters before making a splash.

Presented as a true-crime documentary (which makes this film even more resonant today, especially considering the contemporary cultural obsession with making entertainment out of sordid crimes), Take the Money and Run is centred on Virgil (Allen), a hapless petty criminal with an addiction to theft – whether it be mugging strangers on the street, or robbing banks, he’s compelled to continue stealing, despite the fact that the only thing he is more incompetent at that committing crimes is getting away with them. He becomes increasingly familiar with the inside of some of America’s finest penitentiary, which proves to be incapable of holding him, as he frequently manages to stage escapes, which turn out to be his only talent, even though each attempt only succeeds out of pure luck. Every time he tries to give up his devious ways, whether through getting a decent job or starting a family, Virgil fails miserably and finds himself resorting to his old tricks once again, hoping that this time would be different – but his hopeless incompetence proves to be far more of an obstacle than he anticipates, as his life becomes a cycle of committing crimes and getting caught, almost beginning to enjoy the thrill of being on the outskirts of decent, hardworking society. Rehabilitation seems impossible for Virgil, who finds himself drawn to the idea of making a living as a fugitive, even if the consequences aren’t particularly as attractive as the benefits to him.

Take the Money and Run is a remarkably simple film, which is why it manages to be as surprisingly effective as it is. The underlying storyline is not one that normally facilitates the kind of broad comedy Allen has come to be known for – his style normally looks at socially-awkward outcasts who live decent lives, but still struggle to achieve much. Virgil, while one of the quintessential Woody Allen creations, goes against many of the qualities that make these characters so familiar (and dare we say, predictable). The film works because it doesn’t aim for the big laughs in the way most modern comedies would – it takes a relatively straightforward storyline (a pathetic career criminal keeps getting caught), and compounds absurd situations upon a relatively common premise, which gives the film a certain unexpected charm, where Allen is either leading us down a path of complete surreal narrative anarchy or playing it completely straight, which often tends to be the moments that are the funniest. It isn’t a perfect film by any means – it very often resorts to cheaper tricks to keep the audience entertained, and some of the film tends to be quite predictable, as well as overstuffed with sight gags and broad humour that occasionally distracts from the more subtle moments of comedic genius – but it all works out when we consider how this was an early work from a director still finding his footing, and developing his style – there are worse early directorial efforts that often make the mistake of doing too much too often, and while Take the Money and Run does feel a bit too exhausting in its approach, it works out splendidly when we simply surrender ourselves to its offbeat charm.

It’s a challenge to resist the quirky nature of Take the Money and Run – it’s a film that remains true to all of its intentions, and never tries to be bolder than it actually could be. Arguably constructed as a series of vignettes strung together by similar thematic content, the film does feel somewhat fragmented, almost as if Allen wove together various sketches relating to crime, and asserting the common character of Virgil on them as if to convey the idea that this was a coherent story in the first place. It isn’t a method that is entirely unsuccessful – the film does have moments of outright genius throughout. Yet, it serves to be more of an experiment than anything else, and Allen’s roots as a stand-up comedian, operating from the structure of setting a joke up and delivering the punchline in rapid succession, is very clear – not that this necessarily lessens the experience of watching this film. Take the Money and Run is an incredibly original homage (or rather, a heartfelt parody) to a sub-genre that has always been oddly popular, with the director putting in the adequate effort to elevate it beyond simply mocking the cliches, and instead lovingly paying tribute in a way that the intentions are good, but the execution is exceptionally sardonic, to the point where the absurdity overtakes the passion. Yet, the deficiencies can easily be considered as directorial growing pains, with the final product perhaps lacking tact, but making up for it in raw audacity, which is something that Allen seemed to lose in the latest stages of his career, with the exception of a few instances.

Ultimately, Take the Money and Run is a cinematic representation of pure ambition – Allen was not an established director yet, but rather just a popular young comic trying to enter into filmmaking, which is certainly a difficult notion to consider now, knowing what an influential director he would go on to become. Offbeat and quaint, this is certainly a film that benefits from suspending disbelief and just giving yourself over to the director’s alternative stylings, which certainly result in something thoroughly memorable, if not occasionally underdeveloped, especially when the initial storyline begins to lose momentum, and Allen has to scramble to get enough content in to satisfy the feature-length specifications. Strange, silly and often uncompromising in how it approaches the comedy, Take the Money and Run is an entertaining true-crime parody that reflects on many issues far deeper than it appears to have intended to, and while the filmmaking is certainly evidence of a filmmaker still in his creative infancy, the final product is a delightfully irreverent comedy that never takes itself, nor the subject matter it aims to mock, all that seriously. It’s abstract, bizarre and unforgettably hilarious, which is always a great sign for a film such as this, which has to thrive on the outright audacity to get it made in the first place.