We often tend to think of Woody Allen as a director who mastered the art of cinematic comedy – his generational run from the late 1960s to the present day has provided us with some of the most extraordinary, complex works of humour ever seen on screen. Yet, there can be a point where Allen wanted to be taken more seriously as a dramatic director. This was clear in films like Love and Death and Annie Hall, which were mostly comedic but had a few moments of tenderness that implied that he was interested in venturing into drama at some point. It began with Interiors, and throughout the coming decade, he’d oscillate between comedy and drama – and towards the end of the 1980s, we find September, one of his most sombre and quiet affairs. Having paid tribute to the likes of Ingmar Bergman and Federico Fellini, this was Allen’s opportunity to show his love for Anton Chekhov, undeniably one of the greatest playwrights to ever live, and someone whose work has always influenced Allen, even at his most eccentric. The film is a relatively simple affair, following Lane, who has moved back to her home in Vermont after a suicide attempt – it is in this childhood home that she begrudgingly welcomes a variety of visitors, including neighbours Peter (with whom she wishes to entert a romantic relationship, something he secretly does not reciprocate) and the older and fatherly Howard, and accompanied by her best friend Stephanie, who is in need of a break from the bustling city herself. Lane’s parents have also arrived, but are far too concerned with their personal quibbles to realise their daughter is quietly crying out for help. This reaches an apex over the course of a weekend, when the tensions mount, and the interpersonal relationships begin to deteriorate rapidly, leading to some severe realisations that none of these people is willing to acknowledge. A quiet but forceful work of humanistic drama that finds Allen doing some of his most challenging work to date, September is a fascinating character study that finds the director at his most blistering and sardonic, exploring the dynamic between a group of people who are all at their wit’s ends, desperately grasping onto what remains of their sanity, not realising that they are already in complete freefall from reality.

September does seem to follow a relatively conventional structure at the start – we are invited into the stately home of someone who is struggling to maintain her own sanity, let alone being able to take care of this house, and gradually we find more people entering, which complicates the situation as the pleasantries eventually erode and all we are left with are the painful truths and the unresolved tensions that make it extremely uncomfortable to watch. This is the impetus for the film, and the quality that Allen borrows most heavily from Chekhov, who was known to write plays that were set in a single location and followed the dynamics between various characters, with the dialogue revealing every bit of information we need to understand the context. The themes that Allen chooses to explore are quite interesting in their own right – this is more than just a story of a love triangle or the challenges that come with dealing with a dysfunctional family, especially the difficulties in navigating a relationship with overbearing parents. Instead, its a harrowing examination of mental health and the obstacles that stand in the way when trying to recover – this countryside home goes from Lane’s sanctuary to the location of what seems to be her next nervous breakdown (and perhaps the one that will ultimately push her over the edge – Allen ends the film on a hauntingly ambiguous note), all because she allowed the influence of people who she believed would be able to aid in her recovery overtake her own attempts to improve her mental state. It walks a very narrow boundary between themes, carefully examining the complexities that often arise when self-centred desires overtake basic empathy and compassion. Allen has a knack for exploring various aspects of the human condition, and September is a perfect embodiment of the complexities that exist at the heart of his films, using this story as a means to unpack the various relationships that emerge when half a dozen people, all of whom have their own lives in complete disarray, assemble for a weekend, the prospects of pleasant conversation being almost immediately extinguished as they become more comfortable sharing their innermost existential quandaries.

The extent to which September nestles itself in a more sombre atmosphere is almost admirable – the fact that Allen consistently avoided resorting to comedy, despite the plot having many moments where a stray joke or bit of sardonic wit could have been inserted, is actually quite impressive, and it seems as if he was actively trying to avoid aiming for the obvious approach, which would be to design the film as a more comedic affair. No one would have been even vaguely surprised had he chosen the path of levity, so part of the appeal of September is seeing the extent to which Allen is willing to go to explore these ideas through a dramatic lens. He has as much skill at doing something entirely serious as he does his comedic works – and it all comes down to a matter of intention, approaching the film with a precise attention to detail, each decision made by these characters being intensely compelling and deeply complex and speaking towards a much more profound sensibility. It almost seems as if Allen was actively trying to see if a film like this could be made without any humour at all – this is a story of a dysfunctional family, so it seems easier to fill it with awkward and outrageous moments – the brilliance comes in how he refuses to do the obvious, stripping away every ounce of irreverence and replacing it with the echoes of deep melancholy that become increasingly more common the further we come to understand what was being said throughout. Divorcing the story of a family who are constantly at each other’s throats with the inherent comedy, we’re left with a disquieting, unsettling depiction of people falling apart at the seams, where every interaction seems to be taking place on the verge of complete eruption, and where the future is beyond uncertain for every one of these characters.

In a career spanning over sixty years, Allen certainly worked with his fair share of incredible actors, most of whom were more than willing to take on any role that the director offered to them, under the knowledge that working with him was something of a rite of passage, especially when even the most questionably talented actors were at least partially guaranteed a career-best performance as a result. Yet, only a small handful truly made his work sing in the sense that it felt entirely natural – Diane Keaton and Mia Farrow, both of whom are universally considered to be his muses. September features the latter in one of her greatest performances (if pressed, I’d probably be bold enough to say that this is her best work overall), as a woman who is struggling to realise that her life is not going to get any better until she puts in the effort to change it herself. This becomes almost impossible once she realises it’s easier to get solace from the unseen ghosts that linger around her (whether metaphorically or literally, the film is quite vague about whether her efforts to communicate with those who have passed are real or just her mania-induced illusions), leading to her eventual psychological collapse. She’s joined by a cast of exceptional other actors – legends Sam Waterson, Denholm Elliott and Jack Warden bring warmth and candour, while Elaine Strich (in one of her only major dramatic roles, proving she could be just as incredible when playing in a more sombre tone and Diane Wiest bring so much heart and soul to a film that often challenges us to look beneath the surface, truly trying to understand specifically what it is that drives this narrative. Farrow anchors the film, and the supporting cast offers the right amount of edge to create a memorable depiction of people trying to make sense of a world they know they’ll never truly understand until it is far too late.

It certainly is not difficult to see why September is not well-remembered in comparison to a lot of Allen’s other more dramatic endeavours – it doesn’t have the sincerity of his earlier attempts at drama, and feels slightly unwieldy when sitting alongside some of the later works. It’s not a failure in any way, but certainly requires much more patience than most of his other films, which is not always what we expect from someone whose rapid-fire filmmaking has been his trademark. Needless to say, the film is very good and has many moments of genuine brilliance, scattered in between a dense, dialogue-driven narrative that can sometimes be impenetrable, but is worth the effort once we are able to unearth the secrets lingering beneath the surface. There are some extraordinary performances scattered throughout this film, which is truly ambitious and often skirts around the edges of the human condition in deeply surprising and challenging ways, never giving us all the answers, but also not proposing solutions to subjects that were perhaps most appropriately left open to interpretation. It’s worth it just to see this extraordinary cast of actors, all of whom take the time to develop these characters to be more than one-dimensional archetypes, committing wholeheartedly to the premise that Allen gives to them and working closely with him to make sure every moment is authentic. It’s neither some superb work of comedy, nor an unimpeachable masterpiece of drama, but September is a well-crafted, provocative exploration of humanity and our tendency to default to madness, delivered by a director who was never satisfied with doing the bare minimum, and would always push himself and his collaborators to find some fascinating new truths lingering beneath the surface of everything that we consider to be familiar.