A funny and tender documentary of friendship and acceptance

The light-hearted documentary Will & Harper follows a road trip Will Farrell and Harper Steele take after Harper plays high stakes in the test of their friendship. Their journey is sparked by an email that drops into Will’s inbox. Harper, 61, writes that she “is old now and will be transitioning to live as a woman.” Her main hope is she “won’t lose anyone I care about.” 

A voiceover records their nervous preparation for the trip. Will has only ever known Harper as Andrew Steele; their decades-long friendship began when they started working at Saturday Night Live. Harper imagines how terrifying it will be when, in her dress and heels, she drives over to pick up Will: “I don’t doubt that Will is my friend, but I’m not ‘that guy’ anymore . . . will [he] want to ask me all the questions that you’re not supposed to ask trans people?” While Will is afraid of asking the wrong questions, or, questions in the wrong way, he also wonders: “How long has she felt this way? Why did she keep it in for so long?” 

Sharing memories and encountering strangers

As they travel from New York City to Los Angeles, Harper describes the tortured path she has followed since childhood, trying “over and over to get rid of it.” She used sports habitually “to let people know I was not a woman . . . not that women don’t like sports, but I was trying to be that guy.” By high school, with no one to confide in, she was isolating herself, struggling with a constant sense that she was a freak. She was driven to the point where she had to choose between destroying herself or coming home to the body that she had instinctively identified with since childhood. Finally, Harper comes to recognize how “it’s a wonderful thing when your mind and your body revolts against the unnatural despondent thing you’ve become.” 

Will and Harper set up their lawn chairs and their cooler with snacks and beer in Walmart parking lots, roadside fields and historic sites. Road trips across the U.S.A. have been a favourite way for Harper to travel, but this is her first as a woman. She wonders how she will be received. Wherever their encounters with strangers open to a deeper level, Harper pointedly mentions that she has transitioned. The response they witness ranges from welcome to abhorrence; some encounters leave a wake of messages that brand Harper as a monstrosity, always delivered via social media. And then, beside the Grand Canyon, a hiker comes by and stops to strike up a conversation. A retired counsellor, she confesses how she tried to steer early clients to identify with the body that they’d been born into and regrets how this only deepened their confusion.  

Resurrection and laughter: “the gold that mends”

Humour provides a safe place between them as they travel together. Will and Harper’s friendship is grounded in and built on their work in comedy. In an interview with Image Journal, stand-up comic Charlie Demers describes how the “comedian introduces the incongruity, the tension or discomfort, and the pottery they break is reality, the logos itself. And the laughter is the gold that mends, that heals. Laughter makes something new.”  

Demers’ observations illuminate what I love about Will and Harper. Harper’s email about her transition is disruptive on many levels. On a personal level, this documentary records how lament and laughter mix as Will and Harper together absorb and adjust to Harper’s transition. They weep together as Harper takes Will through a house she’d bought with the dream of living there, safely, as a woman; it has been trashed. Before the trip, Will wonders: “Does she still like shitty beer? Or is she totally into wine now?” Harper in turn questions Will’s definition of bad beer: “he’ll probably want to bring his craft beer along . . . probably tastes like an orange.” Will: “Will some of my questions seem inappropriate?” Harper: “Ask me anything!” Will: “Well, it’s about your boobs . . .”

These seasoned comedians have an amusing way of playing with stereotypes. Will teases Harper about being the “little lady.” Will groans and sulks “This is the worst road trip ever!” every time Harper drives past another Dunkin’ Donuts shop. Whoever is behind the wheel gets to decide where to stop. Will suggests Harper might pay attention to where their car is meandering . . . over the line and into oncoming traffic . . . as they become absorbed in their conversation. 

In the space of their shared vehicle – and for any viewer along for this delightful ride – these two friends hold between them Harper’s vulnerability and Will’s questions, couching all the incongruities, rough edges and unresolved tensions in the mending power of the humour, and the trust that they continue to cultivate. Their hope is realized: that they will not lose each other.