By Ione Gildroy
In a simultaneously traditional and fresh take on the road-trip genre, American comedy legend Will Ferrell takes to the highway with Harper Steele, the ex-SNL head writer who came out as trans in 2022. A touching tale of transition and friendship, the film is genuinely moving and genuinely important, despite its at-times boilerplate feel.
Will & Harper, directed by Josh Greenbaum, chronicles an emotionally layered cross-country road trip between Will Ferrell and his longtime friend (and former SNL collaborator), Harper Steele, a trans woman who recently came out after years of hiding her identity. This documentary captures the duo’s journey, packed with humour, heartache, and discovery, as they travel from New York to Los Angeles, allowing viewers a raw view of Steele’s relationship with her own country, and with herself.
It’s a beautiful film, but occasionally switches between heartfelt vulnerability and what sometimes feels to be overly polished and staged presentation, and this balancing act is both its strength and its flaw. On one hand, Will & Harper succeeds as a buddy comedy and an intimate exploration of allyship, where Ferrell’s well-intentioned, sometimes clumsy support offers glimpses into being a cis ally. The actor’s charisma and natural comedic timing provide a protective barrier for Steele, whose journey is marked by interactions with strangers who represent the best and worst of America. However, the presence of the camera and Ferrell’s celebrity status sometimes blunt the authenticity of these exchanges, leaving the audience wondering if they are seeing the real America or just a curated version of it.
Greenbaum, known for directing comedies like Barb and Star Go to Vista Del Mar, brings a glossy and cinematic touch to the documentary. But this high production quality sometimes feels at odds with the intimacy of the film and the subject. Steele’s story is deeply personal, filled with recollections of her years in the closet, her attempts to transition, and her fears for the future, particularly as she confronts parts of America and its culture that may not accept her. These raw moments are sometimes overshadowed by the documentary’s orchestrated feel, with perfectly timed background music and Hollywood style cinematography, which makes the viewer question the complete authenticity of the film.
Despite these issues, Will & Harper shines in its quieter, unfiltered moments. Steele’s recounting of her past, her fears, and her hopes adds depth to the narrative, as do encounters with people who both challenge and affirm her sense of belonging in the U.S. The film subtly critiques both the ugliness and beauty of Americana, and its lack of a clear thesis mirrors the uncertain terrain Steele and Ferrell are navigating. While Will & Harper may feel too polished at times, its heart is undeniable. For an audience who may not have thought much about trans rights and society, it’s an especially important look into Steele’s life and Ferrell’s allyship. It’s a poignant look at friendship, resilience, and the complex road to self-acceptance in a society that often resists understanding.
Watch Will & Harper now on Netflix.
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