Over time, we’ve seen the development of a very specific kind of cinematic cliche – a stand-up comedian makes their way to the stage and begins to tell their story, which is usually filled with tragedy or some kind of serious subject matter that they are hoping to filter through a more comedic lens. It aligns with the common adage of “dying is easy, comedy is hard”, which is a charming sentiment that has inadvertently led to a flurry of works in which the idea of someone who dabbles in the art of making people laugh is also enduring considerable stress and pain in their personal life, their endeavours in comedy being a kind of therapy. One of the most recent examples of this comes in the form of I Used to Be Funny, the directorial debut of Ally Pankiw, who tells the story of a young amateur stand-up comedian who finds herself growing distant from her friends, family and career after a series of events causes her to not only question her place in the world but ultimately sink into a deep depression, the result of several obstacles that ultimately proved to be her breaking point. From the premise alone, it is clear that this film is retreading common themes, just replacing the central conflict with something different from previous instances, and ultimately reaching the same conclusion, the most expected and predictable ending imaginable. There is nothing particularly notable or special about this film – it is a simple project that offers very little in terms of clear character development, plot progression or insights into the lives of these people and their challenges. It tends to be very obvious in its message (a fatal flaw for any comedy, especially one promoting itself as supposedly more daring than many others), and its contributions are minimal, to say the least. There are a few positive elements scattered throughout, which prevent it from being an overly disastrous affair, but the lack of nuance and clear attention to detail are ultimately some of the reasons it does not live up to expectations or the more intriguing works that populate this genre, leading to a relatively underwhelming and prosaic affair.

The criticism surrounding this film should not be seen as an endorsement for all of the themes it explores, nor an attempt to nullify the importance of the material. I Used to Be Funny is a film that tackles some very serious subject matter and introduces complex ideas that carry an air of importance, especially since they tend to be very relevant to the current social and cultural environment that is driving much of the discourse surrounding gender-based discrimination, substance abuse sexual violence and mental illness, all of which are themes woven heavily into the fabric of the film. There is a gravity to this film that cannot be dismissed, and which we can consider to be the foundation for the narrative. The director was invested in telling a story that touches on these themes, and for that reason, we can understand her perspective since there are many strong components in terms of the theoretical foundation that essentially defines this film. The message the film intends to convey is very clear – life is challenging for anyone, but it becomes even more difficult to navigate when you are a young woman not only in an industry known for its sexism and discrimination but also in a society where women are often at the receiving end of violence and aggression, especially those who refuse to subscribe to the demure, submissive image that insecure men prefer to be around. The foundation of I Used to Be Funny is undeniably strong, and Pankiw has very strong ideas, and a good sense of direction as far as these more important elements are concerned. It is the process of putting them into practice and finding an appropriate entry-point into the story where they can be introduced that begins to prove to be a problem, and we begin to wonder whether it would have worked better as a more straightforward story of a young woman trying to navigate the world, since the comedic storyline adds very little nuance or complexity to the story, and rarely makes much of an impression.

I Used to Be Funny is marketed on the surge of popularity that Rachel Sennott has been receiving for the past few years, since she has proven herself to be an original and compelling screen presence, the embodiment of that crossover between millennials and Generation Z, particularly in the existential angst that comes from being born in between these two generations. This film is promoted as a more serious, complex character study that allows Sennott to play a more grounded, realistic character, which should be appealing to those who advocate for her talent but yearn to see her take on a more layered role, rather than one that depends entirely on her comedic persona. Unfortunately, this is not a gamble that particularly pays off in any substantial way – she is objectively very good and she does her absolute best to make this character seem realistic and fully formed, but it’s not a performance that feels all that special or anything out of the ordinary, and her more subdued approach doesn’t help elevate the part above being merely conventional. Instead, she seems to be just as confused about the tone the film takes, which doesn’t give her much to do – the moments where she is asked to be funny feel awkward, and the more intense sequences don’t resound with any real sense of sincerity, at least not as they are written. Sennott is fully committed to the part, but the film doesn’t offer her too much in terms of complexity beyond the most obvious qualities and doesn’t quite honour the extent of her talents. The supporting cast doesn’t fare much better – not even the outrageously funny Caleb Heron can break through and make this dour film any more compelling since the characterization is not entirely aligned with the overall motives of the film, which ultimately does hamper the experience and prevents it from having as much impact as it could have had with a more solid, consistent approach to the material.

There are promising elements at the heart of I Used to Be Funny, but they begin to fall apart very early on when it becomes increasingly clear that this film is ill-equipped to handle more than one idea at a time, which is troubling considering how much of the story is centred around a tragicomic account of the challenges faced by a young comedian as she attempts to balance her professional career with personal crises, leading to a complete breakdown at which point she is forced to take stock of her mental health and find a way forward. This film is quite simply beyond inconsistent, and it never manages to settle on a particular tone and rather attempts to oscillate between comedy and drama, to very poor effect. It would not be the first time such a subject was addressed in a way that attempts to blur the boundaries between the two – we can think of films like Funny People and All About Nina, which are both incredibly poignant films that look at the backstage life of comedians and how their day-to-day existence can be mired by layers of tragedy. The reason those films can succeed, whereas this one fizzles almost immediately, is because it knows where to draw the line between heartfelt comedy and the more sombre subject matter, which is surprisingly quite far into the process, something that Pankiw is incapable of doing with this film, which becomes far too dour to be entirely convincing when it comes to exploring the healing power of humour, or even viewing it as a form of emotional catharsis. After some time, we begin to question how this film can even consider itself a comedy when it is too bleak and austere, which not only does an immense disservice to the people involved in the filmmaking but also those who they are striving to represent. The complete absence of effort in terms of finding the balance between the moods is ultimately one of the many aspects of the film that falters and becomes such a one-dimensional, overly frustrating experience that holds very little relevance or consistency in whatever vision it claims to be focused on exploring.

As much as we may try and scramble to find long-lasting merits, I Used to Be Funny is not a particularly strong film, for several reasons that become abundantly clear the more we look at the story and the approach the director takes to telling it, which includes a sometimes overly dour tone that betrays the efforts to be an equal blend of comedy and drama. The concept of pairing very serious subject matter with stand-up comedy is beyond overdone by this point, and there is very little this film does to be original or insightful on either subject, ultimately becoming nothing more than a one-dimensional and sometimes quite shallow film that doesn’t quite know what it wants to be or even how to achieve the most fundamental understanding of its character, or the correct way to explore these themes without it becoming hopelessly overwrought. It feels inappropriate to be too overly critical about such a film, especially considering the material with which it was working, and the themes being covered – but yet we also cannot blindly heap insincere praise on something that takes a bold swing but doesn’t quite land in the way it hoped. There is a great film in here somewhere, it is just hidden under layers of mostly unconvincing and heavy-handed storytelling that contributes nothing entirely original or insightful, Squarely is a middle-of-the-road offering that does the bare minimum and hopes that the strength of the story will sustain it, I Used to Be Funny squanders its potential and just generally feels uneven and inconsistent, hampering what could have been a potentially brilliant and exciting introduction to a talented cinematic voice, who will hopefully make some improvements to her forthcoming work.