Pure kismet. In a world where there’s very direct and harsh discussion about transgender people and rights in the United States, it just so happens that one such transgender person happens to be friends with the man who produced some of the greatest comedies of all time. Will & Harper is a perfect inroad for someone open and interested in trying to learn about living as a transgender person in the United States. Because even when the conversations get deep and challenging, 10 minutes later there’s Will Ferrell in Vegas cosplaying as Steve Abernathy as a silly palate cleanser.
Will Ferrell met Harper Steele when the got in at SNL in 1995. Years of great sketches (like this one) and funny movies (recently this ya ya ding dong) have bonded the two into multi-decade, close friends. Harper tested that friendship over the pandemic, finally deciding it was time to transition into the woman she is today. While Will was supportive, he also thought it would be a fun idea to take Harper on a cross country road trip (something Harper loves) for a few weeks, while she becomes more comfortable doing this as her new self and he acts like the audience surrogate, asking all the questions a good-intentioned close friend would want to ask their newly transgendered friend to reforge their friendship in this new era.
Not being transgendered myself, I instantly formed similar questions that Will Ferrell asks Harper, but much less silly. For that reason, anyone scared to go into a conversation with a trans person you know: Will & Harper is perfect preparatory text for you to start your journey. The road trip shows early and often how close the bond of these two people are, and why Will has the opportunity to ask these very personal questions of Harper. The questions range from silly bro-ey ones like “do you LOVE those new boobs?” to stuff like “did you always know you wanted to be a woman?”, definitely questions I had and was afraid to ask when I encountered the transgender people I have met in my life. The key, Harper says early on, is Will is clearly coming from a place of support for his friend. Most of the time, we see Ferrell use his celebrity to disarm excited people who meet him and Harper together, acting as a bridge for people in say, a honkytonk in Oklahoma, to have a positive new experience that should “scare” them according to some politicians and news outlets. Will also learns there’s a limit to that power, like at a Texas BBQ restaurant where he outshines the reason he is doing this documentary for a joke. The big takeaway everyone should have from that specific experience is that next day, when he’s instantly mad at himself for not realizing his mistake, and putting his friend into danger by publicly flaunting his journey for the sake of a Will Ferrell bit.
And through that wonderful friendship bridge we learn about Harper, and her journey: a journey that I personally have hear similar versions of from other trans people like her. It’s not eye opening early, as Harper starts just being Will’s funny friend cracking jokes and buying every Pringle in a Wal Mart, eating them in chairs in the parking lot outside. But as the road trip deepens, we see some firsts for Harper. First time at a big spectacle sporting event in a more conservative state, first trip to a small town dive bar alone, first visit back home. First memory of happiness at a childhood picture. First sad thoughts from living life as a perpetual lie. First thoughts of suicide. As Will (and by proxy, we) hears Harper’s story, those vague understandings of what a trans person is fade away, into the real person sitting right by his side, forced to deal with all of this alone, and scared, how the world would see her, and her hating herself for it. In a movie with multiple disguises and comedy bits, Harper’s real, raw moments are the reason she deserves co-billing in the title, giving the movie all of its emotional power and heft.
In an interview, Harper Steele said she found out doing this documentary that people’s baseline is kindness. Will & Harper shows that feeling. And in a world where it’s easy to feel layers removed from people via technology, my hope is that Will & Harper’s belief holds true, and that each new person you meet has a baseline of kindness, allowing you to be comfortable being fully yourself, whomever that beautiful person may be.