While is a director that has never avoided experimenting with style, although outside of a few radical diversions into very different genres, his films generally maintain a similar quality of being either outrageously funny comedies (particularly in his earlier career) or more self-reflective, complex existential films that blur the boundary between comedy and drama in a way that has become one of his most significant directorial trademarks, and one of the primary reasons he is so cherished as a modern storyteller. One of his more intriguing projects, albeit one that is not often discussed as one of his greatest films, is Deconstructing Harry, in which Allen tells the story of a neurotic novelist who undergoes a process of reflection while venturing to his alma mater to receive a major honour, looking back at his work and realizing how much of his writing has been inspired by his everyday life. A bitingly funny dark comedy that is not afraid of being slightly more serious, as well as one of Allen’s most scathing films in terms of explicit content (he has never been one to shy away from slightly more controversial subject matter, but the vulgarity and sexuality that pulsates throughout this film is quite a departure from his previous comedies, which used implication more than actually depicting these acts or discussing them frankly), Deconstructing Harry is a fascinating experiment from a director who was taking the opportunity to make something slightly more complex, while not entirely abandoning the style of film that he truly appreciated and enjoyed making. Hilariously funny (and often quite creatively crude), but never excessive in the way someone else may have approached this material, Allen achieves something quite remarkable with this film, especially in the areas that would normally be passed over in the hands of someone who wasn’t capable of directing something with as jagged a tone as this, which is precisely why we can view Deconstructing Harry as one of the director’s more ambitious projects, at least in terms of the themes being examined, and their execution, both of which are quite remarkable, even for the standards of a true master.

Throughout the film, Allen is questioning the nature of memory, showing the story of Harry Block through the people that were part of his life in both the past and present. Various characters are woven into the narrative, some of them people in his personal life, others characters drawn from his stories, who could essentially be real people based on how much of his career has been defined by taking inspiration from his life and reconfiguring it under his literary persona. Over the course of the film, we are invited to view brief interludes into the fictional stories that Harry has created, which usually take the form of flashbacks or moments of inserted abstraction, some of them becoming increasingly absurd to show the depths of insecurity and the effortless level of imagination that defines this character. Allen is clearly composing a film around a character that is not easily defined by his own merits, but rather becomes more notable in how his life is filtered through his experiences with others. There have been comparisons drawn between Deconstructing Harry and Wild Strawberries, especially in the over-arching narrative of an academic going on a (meta)physical journey to receive a prize, and along the way reflecting on the past. Allen has a firm reverence for Bergman, to the point where he outwardly mimics his style in creative ways throughout his career – and while each one of these pastiches are well-formed, and usually tends to focus on a single theme more than being outright attempts to parrot the great Swedish auteur’s style, their influence is abundantly clear, especially in this film, which owes a considerable debt to his work, at least in terms of being kickstarted by some of the ideas embedded in Bergman’s work. The primary propellant of Deconstructing Harry is the theme of memory – we all engage in the healthy but sometimes difficult act of self-reflection, thinking back on the past, whether it be in a moment of regret in relation to a particularly disturbing choice, or simply questioning the journey one had to take to get to this particular point in their life, it is often important to ruminate on the past, albeit not to the extent that it becomes a source of tension, whether internally or amongst those that surround you. This latter point is the main divergence between this film and the more serious, sobering dramas that inspired Allen – there is a lot of hostility embedded in this film, and while Harry is certainly one of Allen’s more level-headed characters, the film still takes advantage of the situation to develop him as much more than just a straightforward archetype, a protagonist that is simultaneously a figure of empathy and a tragic hero.

Based on the nature of the narrative, the part of Harry is one that Allen clearly holds affection towards, even if it isn’t quite based on his own life. There is still a rabid debate around who was the primary inspiration for this character – some just assume that it is based on Allen himself (since he had previously made quite a similarly self-reflective film in the form of Stardust Memories nearly two decades earlier), while others see similarities between Harry and authors like Philip Roth and Ernest Hemingway, who often used their fictional works as a springboard to discuss their own lives, using fictional personas to represent real events or genuine philosophical quandaries that both inspired and unsettled them throughout their careers. There is even a possibility that Harry is not based on a single person, but rather serves as an amalgamation of many different artists, Allen borrowing from a range of individuals and combining them to create this character. By design, the role is inherently very funny, and Allen certainly puts in enough effort to make him three-dimensional, elevating him beyond the neurotic milquetoast usually found in these roles. It was important the characterization of Harry was given priority, since our investment as viewers is entirely dependent on our ability to find some aspect of this character that we find interesting or motivating. Allen does well to develop the role, writing the script around the character so much that he is always in focus, although not in the sense that he doesn’t allow space for the other characters to grow and develop. Allen is a terrific filmmaker, and while his writing is slightly more crude and rough around the edges, Deconstructing Harry represents some of the sharp insights he has to offer, with the witty humour combined with a slightly more melancholy tone, allowing the film to be both funny and thought-provoking, especially when it is developing on ideas such as the experience of ageing, the process of falling in and out of love, the artistic process and, the great inevitability that is human mortality, with this film being one of the more potent examinations of death that Allen has made, even though it is a relatively incidental theme. All of these ideas combine to create a vibrant and captivating story of an individual’s journey to self-realization – but as is the case with many Allen comedies, whether or not the character learns his lesson is entirely a matter of individual interpretation.

However, despite being the titular character, most of Deconstructing Harry is told not directly through Harry’s perspective, but rather through the people – both real and fictional – that he encountered throughout his life. As a result, the film is precise in how it constructs its characters, each one needing to be well-written and delivered with complete authenticity but the actors that are cast in the film. We encounter one of Allen’s most eclectic and fascinating ensembles, with the director himself turning in one of his better performances (which is likely due to the fact that he was actually playing a character, with his initial plan to have another actor play the part), delivering one of the more intricate portrayals of artistic malaise and bittersweet complexity we have ever seen from him – this film is undeniably a comedy, but had Allen chosen to make it a drama, he would have been just as strong, and it makes us wonder how he would fare in a straightforward, sobering drama. The rest of the cast is exceptional, with so many standouts that it is impossible to discuss all of them without leaving others out. Whether we have Kirstie Alley, Elisabeth Shue and Amy Irving playing his wives or love interests, or Billy Crystal (in a small but incredible performance) and Bob Balaban as his friends who play an integral role in his journey of self-discovery, or the several actors that take parts as his fictional constructions, the entire cast is splendid, without a single weak link amongst them, which is quite an achievement considering how large this ensemble is, and how not everyone could be afforded as much time as others to share their interpretation of these roles. Allen has always had a way with actors, and the very structure of this film requires him to place a lot of faith in his performers, who are all uniformly terrific, handling the dialogue-heavy script with prowess and elegance, never going for the low-hanging fruit while still being outrageously funny, but still making these characters appear human, which is of vital importance in the overall experience of working our way through this story.

The perfect examination of what it means to be an artist, conducted in a series of moments of self-reflection by a director who embodies so many fascinating themes in his work, Deconstructing Harry is one of the quintessential Allen masterpieces that we often tend to overlook because it seems quite routine on the surface, but in reality it is far more complex and invigorating than perhaps anyone may have anticipated. On the surface, the film seems like a conventional Woody Allen project – it focuses on the daily trials and tribulations of coastal elites as they navigate petty problems relating to their careers, families and identities, with the majority of the story taking place in either stunning Manhattan apartments or in idyllic Upstate New York settings, which may make it slightly more difficult to feel sympathy for these characters on a conceptual level. Yet, Allen has always strived on subversion, and this film feels like one of the more complex depictions of these themes, whereby it is still a comedy, but the humour is much more subtle and nuanced than it appears on the surface, and a lot of effort is put into developing these characters beyond just mere archetypes. Deconstructing Harry has many brilliant ideas, and whether we want to fixate on the performances delivered by this incredible cast, or perhaps the more intricately-woven narrative components, its almost undeniable that this film knows how to handle some challenging subject matter, executing this with a blend of dark humour and deep introspection, which work together to create this astonishing, wildly entertaining philosophical drama. There isn’t much in Deconstructing Harry that Allen didn’t touch on in later films, but the approach taken to some of these themes is extremely original, and easily makes this one of the director’s more underpraised films, and one that will likely be rediscovered by future generations and reappraised as one of his masterpieces.