The premise of the documentary “Will & Harper” is so simple that it almost seems presentational, self-serving, or stunt-y. The idea is, after 30 years of friendship, comedian Will Ferrell learns, through a personal email, that an old friend and former “Saturday Night Live” writer, then Andy Steele (yes, the dead name is used briefly), is coming out as a trans woman. Ferrell is so shocked, wondering what it all means for their friendship. “OK, where do we go from here? What are the ground rules?” he asks rhetorically. He soon proposes going on a road trip across America so the two friends can unpack it all (and, of course, there are cameras there to document it). Yet, if it ever sounds like some puff piece about a celebrity bravely coming to terms with his friend’s transition, rest assured, “Will & Harper” is not that. In fact, by the end, it’s an intimate, deeply heartfelt tale of friendship and acceptance that is moving and will leave you teary-eyed.
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“Will & Harper” begins with the aforementioned email. Steele, who soon becomes Harper Steele, reaches out to the comedian to tell him about her transition. Ferrell is taken aback and genuinely shocked but is already willing to listen and understand, hence proposing the road trip. He notes that Harper always loved America’s heartland, having hitchhiked through most of it, exploring diners, dingy bars, lousy beer, etc., and proposes they try and navigate that same territory in this newfound context.
Ferrell gives some good framework to their relationship, too. He and Steele began at “SNL” around the same time, and when other writers or cast members didn’t understand Ferrell’s comedic sensibilities, then a bit more timid than they would become, it was Harper who was always there defending him, telling the others, essentially, “Give this guy a chance, he’s got something.” The comedian also notes that some of his most boldly absurdist projects, a Lifetime movie (“A Deadly Adoption”), a Spanish language telenovela spoof (“Casa De Mi Padre”), and “Eurovision Song Contest: The Story of Fire Saga” wouldn’t have happened for it not for Harper’s wild comedic ideas.
Both friends seem to struggle with the anxiety of the unknown and how their friendship may never be the same. “Most of us don’t know what the rules of engagement are,” Ferrell says early on. “It’s uncharted waters.” Harper states, “I have no doubt Will is my friend, but I’m not Andrew Steele anymore.”
To this end, “Will & Harper” helps demystify questions or worries others might have in the same situation because when the two friends are reunited and embark on their trip, things are more or less the same, at least regarding their love for each other. Hearteningly inquisitive, in a very human way, Ferrell has lunch with Harper and her two daughters at the beginning of the trip to understand how they felt about the news.
From there, they drive to Iowa, Indiana, and similar heartland stops with several highs and lows along the way. There’s little question that Ferrell or Harper have any doubts about one another or their true feelings, and most of their interactions are jocular and silly as they always were, peppered with Ferrell’s empathic curiosity about Harper’s internal life and how she must have felt keeping this all hidden for decades (these moments, truly the most meaningful and deep).
Some of “Will & Harper” is initially light and breezy, visiting ‘SNL’ and old mutual friends like Lorne Michaels, Tina Fey, Tim Meadows, etc., to the point that it seems like the doc may not interrogate anything too deeply. Still, it pushes outside of it and the two friends’ comfort zone many times, getting into emotionally challenging conversations about Harper’s self-hatred, suicidal thoughts, and general despair in the years before she had become her true self. And this is where “Will & Harper” truly shines, Ferrell generally stepping up as a true-blue friend, curious, compassionate, willing to shut up and listen, and allow Harper to be seen and heard.
Much of the documentary centers around Harper’s fear of relating to the world in her new body, how the world will see her, and the trip in general. Going to dive bars as a crusty old dude, how Harper would describe her old self, is one thing; navigating it as a trans woman is much different.
There are times when people’s generosity and spirit surprise them, such as some bars in Oklahoma where they are welcomed by some Indigenous patrons and an evening watching race car rally contests. But a visit to Texas, where Ferrell attempts to lighten the mood by wearing a Sherlock Holmes costume, goes really south, and the crowd is heartbreakingly menacing. Likewise, another attempt at fun, seeing an Indianapolis Pacers basketball game, goes off-center when the governor comes by for a photo opp, Harper realizing too late that all his policies have been cruelly anti-trans.
These mistakes lead to some sobering conversations about the fears, difficulties, and threats trans people have faced throughout America in the last few years. They also induce some deeply vulnerable and intimate conversations where Harper leaves herself naked and exposed at the hurt she’s faced and both friends in tears. (“I’m not really afraid of these people; I’m afraid of hating myself,” is one of the most gutting realizations Harper admits at one point.)
The doc also addresses some of the notions of its sincerity, also tackling the idea of celebrity privilege that often cocoons and protects Harper on their voyage (not many people are willing to be a dick when jovial Will Ferrell is around, unless its Texas where intolerance radiates off the charts and all bets are off). If anything, Will Ferrell seems like a genuinely silly, happy-go-lucky person who likes to turn many things into constant jokes, but he’s self-aware enough to know where to draw the line.
Directed by Josh Greenbaum (“Barb and Star Go to Vista Del Mar,” “Strays”) and featuring a plaintive score by Nathan Halperin, plus an excellent affinity for the use of soulful music, if “Will & Harper” produces initial skepticism, it quickly disarms with a sweetness and tenderness that is touching and earnest. It’s funny and entertaining, too, never at the expense of the subject matter, and strikes an effective balance between engaging and amusing the viewer while packing in essential conversations about tolerance via the two friends’ worldviews. Ferrell’s warmth and gentle mien is genuinely tender, and Harper is a good-humored figure, achingly exposed about her re-entry into the world.
If anything, this latter quality should hopefully elicit your sympathy. The doc’s effectively and simply communicates the idea that watching people hurt sucks. And that means anyone of any orientation, sexual or otherwise. Seeing people in pain is painful and universal, and hopefully, if any narrow-minded person dares to watch this doc, they can take away the notion that we all just want to live our lives and be our genuine selves in peace and honesty; what’s the harm in that? Will Ferrell also has broad, mass appeal, and the hope might be that this relatable doc can communicate how easy it is for him to understand and have kindheartedness; maybe it’s not that hard for all of us to do the same.
Ultimately, “Will & Harper” says the cost of willingness to understand another person and their truths is nothing more than a worthy investment. It’s a compelling, lovely little journey about friends reconnecting and rediscovering each other in a portrait that’s tender, humorous, considerate, and more than deserving of your attention and care. [A-]
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