Behind every massively successful comedic actor, there is usually a brilliant writer who works closely with them to help develop material. Very rarely do we find comedians being entirely independent when it comes to producing work – even if they craft their own material, there is usually someone who assists in shepherding those ideas or refining them. In the case of Will Ferrell, he has collaborated with many tremendous writers throughout his career, but perhaps the most important is a name very few have seemingly come across, despite it being present in many of his most notable works. Harper Steele, as she is now known, met Ferrell in the 1990s when they were both working at Saturday Night Live, their connection was immediate, and they became close friends, forging a bond that lasted thirty years. However, this is only the foundation of the present discussion, since in 2022, Harper announced to her friends and family that she was going to live her life as a transwoman, which came as a surprise to many of her closest confidantes, who nonetheless supported her decision, even without entirely understanding the scope of what led her to come out or the challenges she has faced over the years. Ferrell was one of these friends who she told initially, and this is essentially the impetus for a project the pair decided to pursue, in which Harper, a self-professed devotee of the open road, would travel throughout the United States, this time as an openly transwoman, accompanied by Ferrell, who would serve as a buffer for places where she may no longer feel safe. In the process, Ferrell takes the opportunity to learn about the transgender experience through openly asking questions, which Harper is more than willing to answer, knowing that they come from a good place of genuinely wanting to learn. This has all been collected into Will & Harper, in which director Josh Greenbaum takes the raw footage of this cross-country trip, which took the pair just over two weeks, and carves a stunning documentary that touches on many issues, some of which are more pressing than others, creating a film that is both essential and wonderfully charming, a combination we don’t often encounter.

One of the great misconceptions that come with discussions around the themes integral to this film is that there is a singular trans experience that everyone handles in the same way. This is the primary point that Will & Harper set out to disprove by looking at Harper’s story. She is someone who decided to transition at the age of 61, so she is by no means a younger person, and such a radical change can bring about its own set of challenges, which is the foundation on which the film is filtered. We don’t often see stories of individuals who transition later in life, with the idea that being trans is somehow a trend amongst younger generations being actively interrogated and proven entirely false by this narrative, which shows how someone can make this leap when they’re much older, evidence that it is never too late to embrace yourself and live your life as freely as possible. Harper Steele is a fascinating figure for several reasons, but as a subject of a documentary around late-in-life transition, she’s a curious case – she has been working in showbusiness for decades, and based on the number of notable people who weave in and out of this film, she made several high-profile friends along the way, but yet she is also not entirely well-known to the public, except the minuscule group that takes a special interest in the niche groups of which she is a member. This slight anonymity gave her the security to transition without it becoming a public matter, as it would be with more high-profile individuals – and this is not lost on the filmmakers, with both subjects being very aware of the disparity between them in terms of fame and what appearing in this documentary implies about their values, which becomes part of the themes that drive this film. Will & Harper looks at trans issues through the lens of being a public figure, focusing on the experiences of someone living her truth while being accompanied by one of the most recognizable actors working today, which in itself evokes fascinating conversations around what it means to be a high-profile ally in a world that is still very much divided on an issue that should not be even closely as contentious as the detractors would like to make it out to be.

Will & Harper is neither the first film to address the experience of coming out as trans and the challenges that are faced by those who take this leap, and it will most certainly not be the last. Yet, there is something very special about how this film navigates these themes, which it does with such extraordinary affection. In circling back to the point of fame, Ferrell is someone who holds a lot of sincere love for Harper, and it seemed logical that he would support her endeavour to have her story told. Yet, it takes on an entirely different meaning when he not only supports her publicly, but willingly goes on this journey with her, using his status as someone with an enormous amount of fame not as a way to curry favour, but as a buffer to distract from his friend, whose fear and insecurity of navigating the country as a transwoman is far more intense than many of us may realize. This is a true testament to friendship, and as much as the film is very impactful when it shows the harsh reality faced by people like Harper (and it certainly does not shy away from showing it in vivid detail – there are some genuinely haunting moments, such as a chance encounter with the governor of Indiana at a basketball game, a pleasant exchange that becomes horrifying moments later when the film points at that this same individual is responsible for signing in a bill banning gender-affirming care – that kind of striking contrast is rarely found in more one-dimensional discussions around the issues), what binds the film together is the deep, loving friendship between these two individuals. It starts as a novel idea – one of the most beloved comedic actors of his generation accompanies his best friend on a road trip, with the promise of hijinx aplenty to follow. Yet, after some time this fades away, and it simply becomes the story of two friends navigating the country, learning about each other in the process of helping one become more comfortable with authentically living her life, and simply supporting a friend through their struggle. There isn’t an ounce of vanity or self-indulgence present throughout this film, which grants it a sense of genuine empathy that we rarely find being this beautifully engaging.

The brilliance of Will & Harper is truly in how the film comes together – the concept is strong, but its one that would only be effective with strong execution, and Greenbaum has the challenge of taking this material and whittling it into something that has a message but also isn’t too heavy-handed that it feels like a lesson or as if the subjects are intending to preach to the audience about something that we are either in agreement on or curious enough to be open-minded in exploring. The film is a wonderful combination of tones, blending both humour and pathos to create a truly compassion documentary. It was unlikely that a film about two of the funniest individuals working in comedy would not be infused with layers of humour, so a lot of that does come through – the chemistry between Harper and Ferrell is tangible, and even the most banal conversations are wildly entertaining, solely because they understand each other’s rhythms and eccentricities better than just about anyone else in the industry. Will & Harper is a film based around small moments, human interactions between these two friends and a range of other people who factor into the story in different ways. Some moments are more impactful than others, but everything is tied together by this sense of empathy that is rooted in both the lighter moments – because this is a very funny film and it would be concerning if it was entirely serious – and the more complex ones, which are pieced together to create something quite beautiful. We learn so much about the two subjects and their lives and careers (it’s not intentional, but Will & Harper is also a tremendous gift to anyone devoted to the history of Saturday Night Live since we’re given entirely new insights into the backstage ecosystem of that show, based on how integral it was to the careers of both subjects), and it is also done through a sense of finding the balance between different elements that factor into the extraordinary story of Harper’s voyage of self-discovery, and the friend who chose to accompany her on this very compelling adventure.

Ultimately, Will & Harper just tells one story out of a myriad, so it can’t be viewed as the definitive text on what it means to be trans in the modern world – and Harper herself would probably be the first to agree with the sentiment that her experience is not the same as those of others, a fact for which she is truly grateful but also somewhat saddened, since for every individual who comes out and is received with love and acceptance, dozens aren’t as fortunate. These people are not forgotten – it is impossible to name every one of them, but the compassion with which the film is made reflects the fact that the community as a whole was right at the heart of the narrative, driving it forward and factoring into every frame we see and word spoken by the subjects. Telling this story through the lens of a road trip was a smart decision, since it immediately gives the documentary structure and a clear end goal (and prevents it from being just a bundle of socially conscious comments), as well as indicating the forward momentum that drives the story and keeps it engaging. The results are immediate and profoundly moving – we are introduced to Harper Steele, someone who has happily been working in obscurity for thirty years, but who I expect is on the precipice of becoming a much more notable public figure. It also shows us another side to an actor like Ferrell, who doesn’t often allow himself to be shown as an unmasked, ordinary individual – and his lack of vanity or desire to be the focus is clear since he is adamant that he is a supporting player in this film, which belongs wholeheartedly to his friend, his insistence on deferring the focus to her being an extraordinary act of empathy and allyship that is almost unheard of in an era where milquetoast statements are the standard for showing support. Beautiful, funny and heartfelt, Will & Harper is a terrific film and a documentary that can both evoke genuine laughter and change entire perspectives,  both of which are clear from the start.