Now Playing — Will & Harper

Harper Steele and Will Ferrell pass the most important test of two central figures in a movie built around a road trip: They’re good company. The two have known each other for several decades, going back to their shared tenure at Saturday Night Live, which began in mid-nineteen-nineties, Steele as a writer and Ferrell as a cast member. The comfort of their camaraderie is clear across the new documentary Will & Harper, but the real mission of the film is to explore where some newfound discomfort might be entering their relationship and how they can overcome it.

Part of the impetus for the road trip is that Steele has recently come out as a trans woman. She is in the early process of transitioning, and Ferrell — and most of her cohorts from the comedy trenches — are still trying to understand the dynamics of their ongoing friendships given the new information. Prior to transitioning, Steele adored long treks across the U.S. that included stops in dive bars and other seedy establishments, the sort of jaunt that she reasonably believes might not be safe for her anymore. Maybe she can venture into those kinds of places with Ferrell by her side, and the two can redefine their terms now that Steele is finally living her truest self.

Director Josh Greenbaum assembles the footage with measured thoughtfulness. Although he undoubtedly has miles of film of Steele and Ferrell doing bits to kill the time cross-country, that is kept to a well-deployed minimum in favor of more honest depictions of the two carefully bonding. Ferrell’s supportive questions about Steele’s transition can sometimes feel like the two are delivering an introductory course on the trans experience for the camera. Of course, for a sizable number of the viewers who might stumble their way to this because of their loud fondness for Step Brothers or Talladega Nights: The Legend of Ricky Bobby, that rudimentary education might be precisely what they need.

What I find most striking about the Will & Harper is Ferrell’s generosity in deliberately using his celebrity to support a friend in need. Time and again, Ferrell leans into the goodwill his comedy career has brought him to essentially ease people into being accepting of Steele. This happens at an NBA game and in the roughest of bars. It’s not a magic spell that works everywhere (a warehouse-sized steakhouse in Texas is a notable exception), but Ferrell wields it with surprising effectiveness in an array of places. These are acts of support more than bravery. They are pure, moving expressions of kinship and love.


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