"Will & Harper," directed by Josh Greenbaum, is a compelling blend of humor and heart. This documentary road film takes viewers on a 17-day journey across the US, following longtime friends Will Ferrell and Harper Steele as they navigate new terrain —both literal and emotional. At its core, it's a story about gender identity and friendship.
Ferrell, known for his comedic roles, offers much more than laughs here. Ferrell and Steele's easy humor is a throughline, but it's offset by poignant moments of vulnerability from both. The contrast between Ferrell's affable care and curiosity and Steele's raw, emotional reflections creates a dynamic that feels refreshingly honest.
The film opens with Ferrell breaking the fourth wall of a documentary with a comical yet meaningful introduction to Ferrell and Steele's friendship, which began in the 1990s on "Saturday Night Live." Their shared history forms the backbone of the film.
They continue to read an email Steele wrote to Ferrell, in which she come out as a transgender woman. Ferrell had no hesitation replying in support of Steele's transition, but he had a lot of questions — questions he'd been hesitant to ask, worried about saying the wrong thing. This was the catalyst for the documentary, creating a space for these conversations to unfold naturally while allowing Steele to navigate the world as a recently out trans woman.
Unlike many documentaries that feel overly produced or engineered for drama, "Will & Harper" is driven by real, often spontaneous interactions. The absence of scripted moments or forced questions gives the film an authenticity that feels rare.
Steele, who is open and candid throughout, makes it clear that she's comfortable answering anything a friend like Ferrell wants to ask. It must be noted, however, that that is not true for all trans people. The film carefully walks this line, never claiming to speak for the entire trans community, but instead offers a personal narrative that offers insight to the trans experience.
Visually beautiful, visably tense
Visually, the film is stunning. Greenbaum captures sweeping American landscapes as the backdrop to Ferrell and Steele's journey, inviting viewers to see a diverse America. In particular, Greenbaum is skilled at translating tense, raw scenes to the screen.
In Oklahoma, the duo visits a conservative, Confederate-decorated bar. Steele enters in solitude to experience being a trans woman in public without Ferrell. The air thins for the viewer as Steele holds her breath on screen, pushed up against the wooden walls of the intimate bar, hesitant to make a move.
Ferrell, meanwhile, is waiting anxiously outside, a rare moment of visible unease for someone who has spent much of his career making others laugh. It's in these quieter, more introspective moments that "Will & Harper" really shines.
A similar, yet more sweat-breaking moment was at their stop in Amarillo, Texas, where the duo takes on the famous 72-ounce steak challenge at The Big Texan Steak Ranch. What begins as a comedic spectacle, complete with a Victorian investigator costume and stage lights (literally), quickly becomes symbolic of Steele's larger journey.
A crowd of Ferrell fans circled the platformed table and recorded them with their cellphones, and the seconds were counting down on the timer, creating an almost suffocating atmosphere. Steele admits she's eating the steak out of nervousness.
The next day, she confesses that it was like her "transness was on display." The film doesn't shy away from showing Ferrell's vulnerability either when he, in tears, admits to feeling like he's failed Steele by not protecting her during the uncomfortable encounter. They later find tweets of live criticism about the documentary they're filming from transphobic netizens.
This vulnerability is interspersed with moments of levity, like when Ferrell wears an American flag Speedo, dad-bod and all, to make Steele feel more comfortable in a hotel swimming pool. Yet these moments of humor don't detract from the film's emotional weight. They remind us that laughter has its place even in the most serious conversations.
In a larger context
Throughout the journey, the duo encounters a diverse array of people, from a retired therapist in Arizona who recalls her early, limited understanding of gender identity to a trans woman in Illinois, who, like Steele, transitioned later in life.
These conversations help frame Steele's experiences within a broader context, touching on themes of identity, acceptance, and the evolving understanding of gender in America, while providing a few sprinkles of political context, referencing anti-trans legislation across the nation.
One of the final stops was a visit to Trona, California, where Steele bought a home in the Mojave Desert years earlier, hoping to live in isolation. The house, now vandalized and abandoned, becomes a metaphor for Steele's journey —once a place to hide, it now represents a past she's ready to leave behind.
She breaks down in tears before entering, having spent working days in the house wearing women's clothes with the curtains closed because she "felt like a monster." In that moment, Steele was grieving the person she once was.
The film concludes with a picture-perfect beach sunset, where Ferrell and Steele sit in their camping chairs, watching the horizon. It's a fitting end to their journey, symbolizing the new chapter in their friendship and Steele's life.
In a world where transgender stories are often reduced to headlines or statistics, "Will & Harper" offers a deeply personal narrative that feels both timely and timeless. The documentary is more than a celebrity buddy film or a documentary about a transgender woman's journey. It's about identity, friendship, and acceptance.
'Will & Harper' streams Sept. 27 on Netflix.
www.netflix.com
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