This movie is a documentary about Harper Steele, a transgender woman who has recently come out to her friends. Because she used to work as a writer on Saturday Night Live, one of those friends happens to be Will Ferrell. He wants to support his long-time friend... but has his own complicated feelings to reconcile. Yet because they are good friends, Will and Harper feel like they can put any big questions right out there in the open. They decide to do so on a two-week, cross-country road trip.
I felt complicated feelings of my own watching Will and Harper, so much so that I'm having a hard time figuring out where to start in praising it. But I think I'll go with: I was surprised and impressed by how real it ultimately felt to me. It did, after all, have two major potential strikes against realism baked right in.
First was the presence of the documentary cameras. The two central subjects of this movie know they're being filmed at every moment. So does every person they come in contact with. When people know they're being filmed, and know that the things they're saying will be seen by others, people often change their behavior.
One of the premises of this movie's road trip is that in her former life, Harper loved criss-crossing the country, visiting dive bars, hanging out with strangers, and perhaps flirting with dangerous situations -- all things that now felt fundamentally impossible to her. Could she reclaim any of that as part of her new self? You might well question how genuine any of that would feel when Harper is traveling with a recognizable celebrity (one form of protection) and surrounded by film cameras (a second). Anyone these two encounter on their trip will behave differently too... right?
Well -- the movie confronts that issue. In one sequence, Harper heads into a dive bar after asking Will to hang back outside. The cameras are still there, but the celebrity is not. Later in the movie, the presence of cameras and a celebrity doesn't stop the crowd at a Texas steak house from being massively shitty. It's a powerful, disheartening moment, but I think it's good for the movie to admit that acceptance of transgender people is not universal. (Far from it.)
The second baked-in element that could have undermined the realism is the fact that Will and Harper are career comedians. Finding the funny is in their nature, and so is diffusing serious topics with a laugh. Sure enough, there are moments throughout the movie where a very deep discussion is headed off with a flippant comment. And yet -- I actually find that when funny people do break past the jokes, things get really profound. I certainly found that to be the case here. When Will and Harper's journey culminates at a run-down house in rural California, the discussion of why they're there, and what it means to Harper, is deeply moving.
Not all the profound moments are about Will or Harper, either. A visit with Harper's sister reveals the most beautiful affirmation you could ask for from a family member. A chance encounter with a retired therapist at the Grand Canyon exposes her profound regret at the way she once handled a patient during her career. And a running gag about a "road trip song" that Will and Harper ask Kristen Wiig to write for them pays off charmingly over the end credits.
Despite the specter of falseness that I thought might hang over the movie, I found it to be nothing but genuine. It evoked in me powerful memories of my own coming out as gay, even as the movie made me think that coming out as transgender would be infinitely harder. And while it sucks that a documentary about a transgender person should innately feel like an "important film," the fact is: it does. Right now especially.
Quite simply, I loved Will and Harper. I was so deeply moved that it lands in the #1 spot of my Top Movie List for 2024.
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