When an artist has been in the industry for long enough, it’s a challenge to not divide their career into different chapters, especially when their style and approach to filmmaking shifts over time. Not necessarily aligned with quality, but more in how they develop their ideas and the kinds of subjects that they pursue at different stages of their career, it is a fascinating process and one that can be quite enlightening when assessing a director’s shift throughout their filmmaking career. In the case of Woody Allen, there are clear delineations in terms of the kinds of stories he intended to tell, as well as the philosophical underpinnings. Everyone tends to have their favourite era when it comes to his work – some adore his gonzo comedies of the early 1970s or his more nostalgic and twee romps of the 2010s. However, his most interesting period has to be the roughly 15-year span between the late 1970s and early 1990s, where his work became much more dramatic (albeit still having a mostly comedic edge), and where he not only paid tribute to his cinematic idols such as Federico Fellini and Ingmar Bergman, but started to implement even more philosophy into his screenplays, many of which become quite layered in terms of the discourse contained within them. Perhaps the most celebrated film from this period (although this is a contentious point since there’s a lot of support for tremendous films like Hannah and Her Sisters and Stardust Memories) is the brilliant and engaging Crimes and Misdemeanors, in which Allen weaves two fascinating stories together – one a dark and deceptive narrative about a well-respected doctor who gets embroiled in a plot to murder his mistress once she threatens to reveal his infidelities, the other a quaint romance between a down-on-his-luck documentary filmmaker and the low-level producer that he soon finds himself falling for – and in the process creates perhaps his most complex and unsettling film, quite a bold statement for someone who produced many exceptional films over the years, with this being one of his crowning achievements for numerous reasons, both in terms of the tangible qualities and the more abstract characteristics that we find scattered throughout this film.

On a purely structural level, there is a certain quality to Crimes and Misdemeanors that makes it quite inventive from the start. It isn’t the first time Allen has told multiple stories within a single film, but it is one of his more experimental efforts, insofar as the film consists of two seemingly separate narratives that have very little in common outside of a few incidental characters that exist briefly in both, which tell entirely individual stories and even exist in different genres. You could make the argument that either of them could have been perfectly sufficient as a film on their own (and the idea that Allen had two concepts that he couldn’t flesh out into features feels like a misguided reduction), but take on an even deeper meaning when placed in contrast with one another. By the time we reach the final moments of the film, where the two protagonists, who had not encountered one another on screen until that moment, or perhaps at all, come together to wax poetic about their crises of identity and their recent experiences, we have witnessed a fascinating series of moments that exist in isolation from one another but have peculiar and intriguing parallels that may take some time to unearth at first, but which prove to be quite remarkable when we realize the connections between them, which prove to be exceptionally deep and quite provocative, both narratively and in terms of the underlying philosophy that drives the entire production. One aspect of Allen’s work that we find to be nothing but true is that he rarely inserts something into his films without reason, and the choice to present these two narratives in tandem with one another, having them intersect in small but intriguing ways, adds layers into the central themes that are being explored throughout, and prove the unimpeachable ingenuity that went into the creation of Crimes and Misdemeanors, a film that garners a substantial amount of emotional and intellectual impact through how it structures its narrative, presenting it has a complex series of moments that intertwine and form something far more engaging, which elevates two very simple, by-the-numbers tales into a more intricately-woven drama.

Crimes and Misdemeanors represents Allen at his most existential and essentially proves to be the coalescence of over a decade of philosophical inquiry scattered throughout his films, coming towards the end of a period where he was most invested in exploring the intricate minutiae of everyday life, and how ordinary people struggle to maintain their morality and sanity amid considerable changes to their lives, or the unfortunate realization that they are not as remarkable as their self-inflated egos much suggest, but instead are rather quite mediocre. The film presents two concurrent narratives that function as snapshots into the daily trials and tribulations of two hopelessly mediocre men as they undergo not only midlife crisis, but begin to question their faith as well as the path they chose, fending off the inevitable sense of regret anyone who has never quite felt like they followed the right path will encounter at some point. Allen has a firm interest in existential philosophy, so it isn’t a surprise that much of Crimes and Misdemeanors is centred around characters debating whether the choices they made are right, particularly in defending their actions and vocations as being more than just delusional attempts to hold onto whatever fragments of masculinity they have (although some may question whether either of them has ever truly encapsulated the idealistic image of what the typical strong, patriarchal figure represents in terms of American exceptionalism – this particular concept is one that the film begins to touch on, but doesn’t quite follow through with as a result of the many other prominent themes that exist throughout), and how their sanity begins to fray when they are confronted with the truth, much of it coming in a rather unexpected form. Crimes and Misdemeanors is a film that asks very challenging questions, and it deliberately doesn’t offer the right answers – the final moments, where we are informed, in quite frank and unfurnished terms, that the meaning of life is non-existent, and that the world is a cruel and bitter place made that way by the self-centred entity that is the human race, leaves very little space for ambiguity, and shows that not only is this one of Allen’s most existential films but also perhaps his most bleak and unnerving.

As was the case with most of his films, particularly during this era of his career, Allen enlists quite a strong ensemble to bring this story to life, which allows for a fantastic blend of recognizable stars and more obscure, working character actors, many of them plucked from the New York theatre world (to which Allen seemingly had unfettered access), who form the basis for this tremendous cast. Crimes and Misdemeanors is led by Allen in one half of the story, and Martin Landau in the other, which proves to be an unexpected pairing of protagonists, but one that works perfectly, especially since this is a story about two men struggling to overcome their existential crisis, working through the sudden realization that they are hopelessly mediocre, and will never amount to anything that they used to believe was possible when they looked at this bitter and cynical world through more idealistic, opportunistic eyes. The two actors are wonderful – Allen is playing a typically neurotic, insecure nebbish, not doing anything particularly noteworthy, whereas it is Landau who is most surprising, taking on this complex, layered character that required an actor of a particular stature, someone who could skirt around the darkly comedic edges without contributing to it, and who we genuinely can imagine having their life fall apart as a result of a few poor decisions. This film proved that Landau could rise above being merely a reliable character actor, and while he essentially only occupies half of the film, he is the de facto star of the project, being by far the most memorable aspect, so much that not even Allen in one of his very best performances, nor the supporting cast (which includes the likes of Mia Farrow, Alan Alda and Anjelica Huston) could even come close to achieving such extraordinary results from a character this unique and challenging. There is a very real possibility that Landau delivers the best performance across any of Allen’s films, but that’s an entirely separate conversation.

However, if we put aside the more serious elements of the story, we soon learn that Crimes and Misdemeanors is a genuinely very funny film, and contains the exact kind of sardonic, existential wit that Allen has proven to be capable of infusing into just about any story. It’s important to not allow the more complex aspects of the plot to distract us from a film that is as much about exploring morality and crises of identity as it is about observing the sometimes meaningless intricacies of everyday life. Arguably, most of the humour comes from the half of the story occupied by Allen’s character, since it’s almost impossible for him to not be funny on screen, or at least take advantage of his distinctive self-deprecating persona for the sake of revealing different ideas within the story. His masterful ability to oscillate between tense philosophical drama and heartfelt comedy is a great skill, and it leads to the realization that the reason Crimes and Misdemeanors work so well is because of the tone. The film is mostly driven by atmosphere, both in terms of the individual stories that constitute this story, and the juxtaposition that emerges between them. It’s not all that easy to categorize this film, and any attempt to shoehorn it into a particular genre isn’t likely to yield many notable results. Instead, we find that the mood is what keeps the film so fresh and invigorating, since not only are we unable to fully unpack precisely where the story is heading, but several surprises are lurking around each corner of the film, some of them genuinely delightful, while others are darker and more sinister, forcing us to assess our understanding of the plot – what we at first thought was hilarious observational comedy about these characters soon turn into the foundation for some profoundly tense and unsettling commentary, and the film’s gait proves to be a tremendous strength, particularly in forming something so incredibly concise and meaningful at the same time, a peculiar comparison that works exceptionally well in the context of the film and its sometimes overzealous approach to the human condition, a fascinating trait that becomes one of its defining qualities as the narrative progresses in sometimes unconventional ways.

There is an argument to be made that Crimes and Misdemeanors is Allen’s greatest film, with a steady stream of support making it clear that many consider it to be the epitome of his work as a director. It is certainly the final entry into this particular chapter in his career, where he spent the decade exploring the inner lives of complex characters, placing them side-by-side with teachings from the philosophers and artists that he revered. He would attempt to return to this kind of storytelling with films like Coup de Chance and Irrational Man (both also very clearly existential works revolving around morality and the ethics of pursuing your ambitions, even at the expense of those who may become victims to one’s egocentric and perhaps even violent delusions), but they were barely as successful, particularly because Crimes and Misdemeanors came about at a time when the director was experiencing his most inspired burst of creativity, leading to several exceptional films, this being amongst the very best. The qualities that make it so intriguing and complex are not difficult to understand – primarily, this is a film built from genuine attempts to understand subjects such as morality and the more challenging aspects of being human, which are very much in line with a lot of the director’s other work, which often took shape through asking particular questions. Then layers of humour and melodrama are added onto this, creating a vibrant and captivating dark comedy that is as provocative as it is entertaining. Superbly well-written and driven by a sense of authentic philosophical pondering, as well as not being afraid to push a few boundaries for the sake of making its point, Crimes and Misdemeanors is one of Allen’s crowning achievements, a nuanced and brilliant character study that may seem simple on the surface, but which proves to be far more complex than we would initially expect, making it one of his smartest and most insightful works, and a film that is as resonant today as it was 35 years ago when audiences were first witness to this bizarre and captivating tale of forbidden love, existential dread and the sometimes pitiful hilarity that comes with simply being alive.