In about two weeks, we will be celebrating the fiftieth anniversary of one of the most audacious and influential documentaries premiering at the New York Film Festival. Portrait of Jason is one of the most unheralded films ever made, a documentary that is so astounding in its simplicity, but so broad in its multitude of themes, it is impossible to not be moved. Portrait of Jason is a film that I waited a very long time to see, it serving as a cinematic Holy Grail of thoughts, hopelessly out of my reach. However, once I saw it, I decided it was perhaps the most extraordinary film I have ever seen, and much like the work of Agnès Varda (of whom I am never afraid to hide my utter adoration), Portrait of Jason and its creator, Shirley Clarke, motivate me to want to make documentary films as extraordinary as this. Needless to say (leaving the bouncing praise behind for a moment), I adore this film and everything about it

Two filmmakers, a camera, an apartment, a high-supply of alcohol and one very charismatic man are the only elements of Portrait of Jason. To call this a simple film is to say too much. Portrait of Jason is a nearly two-hour discussion with Jason Holliday (real name Aaron Payne), an obscure homosexual, African-American cabaret performer and comedian who has a seemingly endless supply of anecdotes and stories to tell. When Shirley Clarke and Carl Lee set out to make this film, all they needed was Jason to start talking, and let me tell you, he talks. For the entire duration of this film, the camera lingers on Jason as he progressively becomes more and more intoxicated, telling stories about his past, present and hopefully his future. As he gets deeper and deeper into his narrative, Clarke and Lee start to provoke him, and the growing hostility between the filmmakers and the subject becomes evident, resulting in a breakdown that is the single most extraordinary explosion of emotion I have ever seen in a film, fictional or not.

Portrait of Jason is a film that will doubtlessly seem incredibly boring – and on the surface, it certainly doesn’t have any appeal other than the fact that it is a considered a seminal piece of independent documentary filmmaking. If I may play devil’s advocate, Portrait of Jason is a film that just doesn’t seem all that exciting – many people won’t even watch a full interview with a notable cultural or political figure, let alone some obscure, unknown cabaret performer that was not remarkable in the traditional sense either before or after this film. For the most part, Portrait of Jason is just a set of ramblings from a likely alcoholic as he lets out his frustrations, and his filmmaker friends take advantage of his inebriation to let out their own frustrations and provoke him for the sake of exploiting his clearly fragile (but well-hidden) emotional state simply because it makes for riveting cinema, because as Jason says, “people love to see you suffer, and believe me, I’ve suffered” – this is a film that builds on the intensely human desire, the schadenfreude,  to see people at their lowest moments. Everything about Portrait of Jason should be equal parts fascinating and revolting.

However, the truth is that Portrait of Jason, while ethically dubious, is one of the most incredibly complex films ever made. There is a belief that for a film to be profound, it needs to have several motifs and a sense of allusions and imagery pertaining to some hidden grand narrative. With Portrait of Jason (as well as her previous films, namely The Connection and The Cool World), Clarke proved that this notion wasn’t exactly truthful. All she needed was perhaps the most charismatic man to ever be committed to film, a camera (and quite a bit of film to record him on) and a little provocation. Throughout this intensely personal odyssey into the mind of Jason Holliday, Clarke manages to explore themes that existed throughout her films and the films of her contemporaries that were making similar (although not quite analogous to Portrait of Jason) films at the same period in time.

Portrait of Jason is a bohemian odyssey. Jason is an African-American, homosexual cabaret performer that (by his own admission) has found himself in a variety of jobs, moral and immoral. Through his testimony, Clarke captures the raw zeitgeist of the bohemian mindset that existed in the period of the Civil Rights Movement. She takes a truthful and often very disturbing approach in how this film was edited (because it would be odd to say that she crafted the progression of the story, because, with the exception of the filmmakers in trying to direct the narrative towards a particular direction, everything about this film begins and ends with Jason and his remarkable ability to tell a story). Issues of race, homosexuality and class struggle shine through in Jason’s stories, as he tells stories that apply to him, but speak to a large set of problems that existed at the same time. Portrait of Jason thus manages to be a deeply personal testimony, as well as a statement on the underlying problems that existed in society at that time, through the eyes of someone who experienced it first-hand.

Jason himself is such an odd figure. Normally, anyone that is given the opportunity to have an entire film like this made about them is someone of notable standing – someone recognizable and who people would actively seek out to spend two hours of their lives listening to (that speaks to the very troubling concept of celebrity worship, but that’s an issue for another day). However, it becomes quite an interesting anthropological study to make a film about someone obscure and unknown, with the audiences first (and likely only) interaction with those individuals being in the confines of the film. It is something that Clarke was particularly good at, and what the likes of the aforementioned Agnès Varda and the patron saint of these kinds of voyeuristic explorations into human nature, Errol Morris, have mastered. Yet, neither has ever been able to achieve what Clarke did here, which was putting probably the most charismatic individual onto film in such a way.

Wearing his thick bifocals and a smart-casual suit popular with cabaret performers of the time, and occasionally utilizing a hat or two, Jason Holliday becomes a part of our lives, armed with his seemingly bottomless glass of liquor, and making sure to use his powerful weapon of incessant wit, Jason worms his way under your skin and remains there, a welcome stranger in our lives. There isn’t much redeeming about Jason, other than the fact that he is despicably charming to the point where you are persuaded to feel sorry for his plight, while still somewhat taking the side of the provocative filmmakers who push Jason to the point of near-existential despair at his poor life-choices. If there is one word to summarize Jason Holliday, it would be this: human. He is a deeply human, flawed individual who has earthly vices and real temptations that show him as a virtuous sinner. He forms a connection with the audience that just never fails to create the image of someone who is so extraordinarily larger-than-life, yet so grounded in reality. His quasi-downfall at the hands of the filmmakers is painful yet sadly fascinating to watch.

At first glance, Portrait of Jason is nothing more than the increasingly drunken ramblings of a charismatic raconteur. It’s low-budget independent sensibilities are only accentuated by the fact that this film made over a few hours in Clarke’s penthouse apartment. This is a film about Jason, but it is also a film that goes into thematically dark places, even if it was completely unintentional. This film is a tragicomic account of the rise and decline of someone who longed for fame and glory but has sunk so low, he is at the point where he needs to writhe on the floor in existential agony while some filmmakers, or rather exploitative voyeurs, record every nuance of his growing breakdown. This is a great social film because we can see the plight of the gay and African-American communities reflected through Jason – because beneath his upbeat, classy persona is a hustler who has struggled with the social, political and economic climate of the United States during a very polarizing moment in history.

The prejudices that came with being part of two very marginalized groups in a period of social unrest, where everyone was against you based on characteristics that you could not change, as well as the challenges of simply being unique and having your own individual talents, are all reflected in Jason’s heartbreaking (albeit very entertaining and lighthearted at times) narrative. There are even some slight elements of stand-up comedy present in this film, because Jason clearly takes the opportunity to use this film as a showcase for his own unique talents and abilities, never failing to prance about like he was performing on stage in one of his nightclub performances – this may seem like it would be quite entertaining to watch, but it makes his breakdown towards the end of the film just so much more heartbreaking – he is just someone who tried to make it but had other factors holding him back from ever being a star. There is a moment in Portrait of Jason where he comes to the realization that this film is his only chance of ever performing for the widespread audience that he always dreamed of – and seizes the opportunity, which results in a heart-wrenching attempt to show the world his talents, while knowing he’ll never reach the fame he thinks he deserves.

Portrait of Jason is a film that will bewilder a very many people. It isn’t a particularly exciting film, and it requires a vast amount of patience. It also needs the audience to have some interest in the human condition, and the ability to get lost in the words of Jason. His stories are very often hilarious, but also deeply personal and very often depressingly bleak. There is a certain joy gained from watching Jason giggle at his own jokes or position himself as some notable cultural figure that has an opinion far superior to those of others, as well as a life much more interesting than your average gay, black hustler in the New York City of the 1960s. It is an odd, riveting and beautifully made film that serves to be a great precursor to the cinéma vérité movement that would give birth to reality television. The only difference is that with Portrait of Jason, Clarke doesn’t construct an ideal reality, but rather allows Jason to tell the story of his life in his own way, and while it is sometimes very difficult to follow, as Jason’s inebriated state (through his frequent alcohol and marijuana intake) makes his stream-of-consciousness narrative extraordinarily fascinating, but ultimately abstract and almost incoherent. It is the one true joy of this film, that we are able to see an individual dissected by his own words, opening up his past fully and explicitly for all to see. It almost goes beyond reality.

Portrait of Jason is a beautifully complex film, with a flawed but entertaining figure at the center who lets us into his life, where he shares his most joyful memories as well as his darkest secrets and anxieties. It is a beautiful one, and certainly one of the very best documentary films ever made. Now, fifty years on, it is important to look back at such an important film and look at Jason as both a unique individual who imparts unconventional wisdom based on his own life, as well as a prophetic figure who makes some scathing statements about society. One aspect of Portrait of Jason that I found of deep interest was the fact that half a century later, it remains relevant to the current social, economic, political and cultural state of our world, and you can come to your own conclusions as to whether or not that is a good thing or not. More than anything else, Portrait of Jason is a deeply human story that will leave you with conflicting emotions of laughter and distress, as one watches the story of Jason Holliday unfold with angst and joy, until his mind is laid open for us to inspect, the man himself a broken and complex individual who has nothing to give expect his past. Such a beautiful, unheralded film from a true pioneer of documentary filmmaking.