SUNDANCE FILM FESTIVAL --- “Will and Harper” is a must-see documentary starring the larger-than-life comedian Will Ferrell and his best friend of 30 years, Harper Steele, who in 2020 shocked all of her friends when she came out about her transition.
As a man, she loved road tripping across America, stopping at truck stops and dive bars, monster truck rallies and sporting events, but after coming out as a trans woman, she realized that part of her life would no longer be the same. Being a woman means you are far more vulnerable being by yourself on the road, but being trans presents an even higher risk of ostracization or, worse, physical danger. To help move through this new stage of life, Ferrell and Steele band together to revisit some of Harper’s favorite road-side attractions — with the privilege of a beloved celebrity by her side to act as a buffer and support. (The two acknowledge this is an advantage not typically offered as part of the trans experience.)
The film, directed by Josh Greenbaum (of “Barb and Star Go To Vista Del Mar”), beautifully and candidly addresses the confusion and discomfort that can come with the changing dynamics of friendship when one comes out. But there’s enough effortless humor in the story that will have you laughing even while you cry throughout.
There is plenty to say about the film’s notes on relationships, its exploration of transness, and even its all-star collection of cameos, but what struck me was how little I knew about how to really master the art of the road trip.
Harper Steele knows what she is doing. She spent her life hitchhiking, drinking her favorite beer (the polarizing Natty Lights), and enjoying the freedom of the open road.
The two met while working for Saturday Night Live, when Steele connected with Ferrell’s unique sense of humor and understood how to write sketches that would play to his strengths. Greenbaum makes use of the SNL connections by incorporating some familiar faces into the film (Tina Fey, Tim Meadows, Kristen Wiig), while also making time to center Steele’s story by introducing us to her family and her childhood home.
“Will and Harper” is much more than a comedic road movie. It is a pilgrimage through the emotional complexities of coming out and exemplifies the power of listening to learn. There was a side to Harper that had always been hidden from her closest friends and family, and making the film provided her the opportunity to try relating her experiences out loud for the first time. In one heartbreaking admission in the film, she unpacks her self-hate, explaining that it is difficult not to view her new self as a “freak” after so many years of harboring that level of judgment toward herself and those like her.
There are plenty of honest moments where their naivety gets the better of them, or the two face hostility from strangers that sours an evening, but more often than not the film manages to inject hope and joyfulness into its 114-minute runtime – falling on the lengthier side of the average documentary. It is paced exceptionally well and Will and Harper are both charming and eccentric. By the end, I found myself only wishing that it wouldn’t end.
The film understands its own limitations and doesn’t seek to solve anything about the battles that trans people face every day, but it starts a conversation. It offers a rare look at friendship that will have audiences feeling hopeful, moved to tears and maybe even itching to go for a long drive.