Will & Harper – a charming but impersonal road trip movie

Will Ferrell and his best friend Harper Steele embark on a cross-country road trip, reflecting on Steele's experiences as a recently out trans woman, in Josh Greenbaum's meandering but sweet documentary.

If country roads were designed to take one home to the place they belong, what of those who find themselves at odds with the very roads they once found solace in? This is precisely what Josh Greenbaum’s Will & Harper questions as it follows former SNL writer Harper Steele (a recently out trans woman) and her best friend (Will Ferrell) on a road trip across the USA.

It’s a simple premise for a simple movie – one that spends its runtime serving as something of an extended therapy session for Steele. Or perhaps it’s more reasonable to call it exposure therapy, complete with Steele opening herself up to friends and strangers alike for mildly intrusive questions, plenty of misgendering, and sincerely heartbreaking personal revelations of what existing as closeted did to her.

For Steele, travelling across the country while presenting as male was a source of comfort, taking great pleasure in finding dive bars and seedy joints to vibe with strangers. It’s heartbreaking to watch her explain how much anxiety she has over something she used to love simply because of her transition, but that is exactly why Ferrell is there. He is both a pillar of support and a means of bringing out the laughter and joy that exists in Harper, and there’s something beautiful about the way the two bounce back and forth sometimes.

The thing about Will & Harper is that so much of it feels polished to the point of unbelievability. Ferrell’s fame obviously offers some level of safety net, as does the presence of an unhidden camera, but it extends beyond that. Where casual conversations between the title “characters” come across as honest and playful, as do those with people from Harper’s own life (including her children), many of the set-ups with strangers across America come across as not quite staged, but certainly scouted for safety and sanitized to the point of questioning their veracity. There’s no urgency, no danger, which is certainly better for the trans woman at its core, but it makes these scenes fall flat and there’s not much Greenbaum can do to enliven them.

This kind of neutrality is something that’s perfect for a cis audience inexperienced with anything trans, but it makes one long for more of the highs and lows that the film showcases. An extended bit with another trans woman that Harper met in the past, where the two discuss their experiences, is genuinely lovely and revealing, as is one of Harper’s lowest points where she reveals the lengths she took to initially transition and how much she felt like a monster. All the cameos from former SNL players and writers (save for Kristen Wiig, who is asked by the duo to write a silly little song for their road trip) weigh the film down, but presumably serve as another layer of relatability, or “normalcy”, for an audience “unfamiliar” with trans people.

Its lack of any thesis other than bare-bones education makes Will & Harper a hard film to label. It’s a documentary that feels a little too deliberately manicured for its own good, it’s not enough of a portrait of these small American towns to be considered a travelogue, it’s not especially educational in the way it purports, and it isn’t particularly funny enough to be much of a comedy. As such, it’s just floating in a no-man’s land, a charming but impersonal film about a deeply personal journey.

Published 11 Sep 2024

Tags: Harper Steele Will Ferrell