“Will & Harper” & the Long Road of “Transitioning” To a True Self

We Americans are suckers for buddy road trips. Two young-ish guys, a guy and a gal, two gals, it matters not. Fill up a suitcase, an ice chest and the gas tank, take the top down if you can, plop into the car, and tool on down the highway, stopping where and when you please, keeping the trigger finger in your brain always cocked for adventure.

It’s a vast and gorgeous country, after all, and most of the people in it are right nice when you get out and meet them face to face. Road trips are a fine way to learn and appreciate that, and in the process, they tend to serve as a rite of passage to better understand one’s self, one’s country, and one’s place within it.

Little wonder that we like road movies, too, riding along with the pals on screen as they enjoy the luxury of imaginative scriptwriters who toss them into one boffo or tense situation after another.

The ongoing, trip-long Q&A sessions allow Ferrell to listen—closely, with genuine curiosity and a kind of radical acceptance and faith that his beloved friend is telling the truth about herself, from the deepest reaches of her being.

The comedian and actor Will Ferrell and his longtime creative sidekick, the comedy writer formerly known as Andrew Steele, add a few significant twists to the road trip movie genre in their current Netflix release, “Will & Harper.”

For one thing, at 57 and 61, they’re old guys—or at least a couple of decades beyond the more typical road trip age range. But far more importantly, this road trip has an unusual impetus.

Just a few months prior to its launch, Steele had begun transitioning to the female gender he had longed to inhabit ever since he went off to kindergarten more than a half century earlier and lined up with the girls as the girl he insisted he was to both his slightly taken-aback mother and teacher.

In all the intervening years comprised of getting educated, married, developing his career and fathering children, the feeling had never left him.

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So he begins hormone treatments, and decides to send her old (see how easy that was?) “Saturday Night Live” compadre an email that begins: “Hey Will, something I need you to know. I’m old now. And as ridiculous and unnecessary as it may seem to report, I’ll be transitioning to live as a woman.”

After reflecting on her struggle to come to terms with the drivenness of taking this action despite the certainty of it being challenging, arduous, joyous and potentially dangerous, she ends with: “Mainly, I hope I don’t lose anyone I care about. Thanks, Name forthcoming.”

Unsurprisingly, Ferrell is gobsmacked, which is not at all to suggest revulsion. More like the “Whoa!” he expresses to the camera. Followed in short order by, “O.K., where do we go from here?”

Where they go at least in a geographical sense is a road trip that starts in the snows of New York and ends on a sunny beach in southern California, with notable stops in Indiana, Oklahoma, Texas, Las Vegas, the Grand Canyon, and the California desert. The trip is Ferrell’s idea, based on Steele’s long romance with out-of-the-way places in America’s hinterlands, the divier the bars and sparser the landscape, the better.

Where they go internally, however, are places with only the sketchiest of existing maps, to such a deep, tender and tremulous excavation of human emotion, friendship, acceptance and identity as to make the angels weep in wonder. Punctuated throughout by the typically zany and hilarious byplay between two gifted comics doing what they do best in life—and inviting us along for the ride.

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There’s much to love, laugh and weep over throughout this film, but I will shy away here from too many particulars that might spoil anyone’s fresh take. (Although you definitely should not go out to reload the popcorn bowl when the Harper-on-a-unicycle-in-high-heels scene plays out.)

“Voyage of discovery” is a hoary cliche that applies all too well to what percolates throughout this much-lauded romp through America and a 27-year friendship whose bonds will be, if not tested, at least transformed as neither party could possibly have imagined at its beginning. Ferrell has a million questions, Steele encourages his asking. (One reason surely being that she has far and away more to sort out for herself in this journey than does her faithful interlocutor.) To his credit, Ferrell dives right in.

No doubt most importantly, the ongoing, trip-long Q&A sessions allow Ferrell to listen—closely, with genuine curiosity and a kind of radical acceptance and faith that his beloved friend is telling the truth about herself, from the deepest reaches of her being. And this, I think, is the key to the whole rigmarole of “accepting” transgenderism as just one more course correction for the infinite variables that nature visits upon her creatures.

Is gender dysphoria, the depositing of a wholly female psyche in a male body and vice versa, a “mistake?” Well, sure, if we regard “mistake” as any genetic variation that lands one outside the “normal” range of body type, eye color, sexual orientation, propensity for disease, and a decided inclination to hate or love the Yankees with all one’s strength and will.

But here’s the thing: human beings have created fixes for an astonishing range of such “mistakes” since our first forays into a scientific-mechanical mindset. And when those fixes become available, lo and behold, people run to embrace them. Who’d’ve thunk?

Now we have a fix for gender dysphoria, and one cannot listen closely to accounts of those who suffer from it without that bit of biblical business about “judging not” coming quickly to mind.

I’ll wind this down now by highlighting in general terms three scenes that for me, clearly spell out the difference between actually knowing and hearing from a transgender person and just reading about him/her from some fear-mongering source seeking to score points off it for electoral or pinched religious purposes.

Two early scenes in Indiana and Oklahoma place Ferrell and Steele in classic dive bars, where they engage with mostly cowboy-or-manual labor-garbed customers. Obviously, they’re accompanied by a camera crew, so attention will be paid. Our road warriors proceed to explain the context for the cameras and their journey, some discussion ensues, and the response is uniformly positive.

Face to face with an actual person rather than an abstraction on a screen, natural human warmth works its spell.

Then it’s onto Texas and a massive steak house where Ferrell decides—unwisely, it turns out—to make it a show by featuring himself attacking a 72-ounce steak while also announcing to the huge crowd looking on from multiple floors that Steele is transitioning, etc. Far more spectacle than engagement, a kind of unease becomes readily apparent, followed in the next scene by the pair back in their hotel room, crestfallen, noting ugly social media responses by anonymous onlookers who hold forth from their perch of narrow minds unaffected by any actual, person-to-person engagement.

I remember now many years past when the very existence of gay people demanding their right to be out and open in society faced huge backlash by those who thought their orientation to be some kind of sin or disease. I always felt compelled to ask such people in a tone somewhere between pleading and exasperated, “Have you ever actually TALKED to a gay person? Have you ever asked what their lives are like?”

The answer was most always no, of course. Ignorance borne of sheltering in silos usually begets judgment of the withering kind, for which the antidote is always curiosity, openness, engagement, and recognition/remembrance that the person in front of us is far more brother and sister than not. Unfortunately, because people and cultures tend to evolve very slowly, groups outside the mainstream most always have to travel a long and tortuous road before alighting to that place where they are seen as such.

But that’s the beauty of road trips, in all their forms, and the wondrous adventures they uncannily and ultimately hold in store, at various surprising miles.

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A running gag throughout the film is Ferrell and Steele prevailing upon an old friend to come up with a song to commemorate their journey. Weeks & weeks go by as they leave occasional voicemail messages…with no return calls. Then the film ends, the credits start to roll, oh well, and suddenly…

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