Joy can often be found in the most unassuming places. In roadside diners, biker bars, even parking lots. It’s nestled between our relationships with friends, family and even the strangers one tries to make laugh. But what if the place one visits most often, the interiors of the heart and mind, has a hole where joy should be? What is there to do when one lacks the self-love and sense of identity needed to live authentically? At 59, comedy writer Harper Steele found her answer: write an email.
Like many others struggling during the COVID-19 pandemic, Steele found solace in the digital space and composed an email detailing the transgender identity she had been struggling to elucidate her whole life. Now, having had distance from the everyday performance and a therapist to guide rather than shame her, she could re-introduce herself to those closest to her.
Will Ferrell was one such recipient. The virtual insight into a dear friend’s secret pain provoked Ferrell to want to catch up with Steele and her journey with gender dysphoria. But, he had the idea to take this reacquainting a step further — 3,000 miles further. What if two friends got to know each other again, asking one another the tough questions on a road trip from New York to L.A. while a camera crew filmed them?
Steele, a devoted road traveler, was intrigued but hesitant. Eventually, she agreed, and now the documentary Will & Harper is in premiering in select theaters, including Iowa City’s FilmScene. It will be available to stream on Netflix starting Friday, Sept. 27.
Will & Harper is not the end-all-be-all of films chronicling the trans experience. Such a film is unlikely ever to exist, and Will & Harper wisely does not proposition itself in such a way. Steele understands her story is only her own; not many trans folks have a celebrity to cushion their reintegration into society. But the documentary endures as something precious: a tale of the allyship and reassurance too many trans people go without.
The Iowa City native sat with Little Village to reflect on the film, her Midwestern beginnings and the personal expedition that has continued since the car was parked for the last time on her cinematic road trip.
Growing up in Iowa City and in the wrong body, Steele said her school routine became “sitting in the back of a class and getting C’s, not paying attention, and just waiting to make everyone laugh.”
“If you go back to probably third grade … the transness in me was there causing a lot of anxiety and nervousness,” Steele told Little Village. “And so I generally became a class clown. I needed people to laugh at me to sort of deflect who I might have been because I was afraid of that. I was a class clown my whole life.”
Comedy existed in this liminal space for Steele. As she got older, it was a form of community and expression, but also a distraction from the parts of herself Steele did not have the tools to reckon with.
At the University of Iowa, Steele met future comedy writer-actors Steve and David Higgins and became interested in their improv comedy group. Laughter was at the heart of their connection. Steve and Harper would go on to write for Saturday Night Live, and it was there that she first met Will Ferrell. Ferrell’s personal brand of comedy wasn’t understood by everyone behind the scenes at SNL, and he bonded with Steele over mutual feelings of being an outsider.
But what makes their lasting camaraderie so special is their commitment to intimacy beyond jokes and their refusal to cower behind comedy.
Ferrell doesn’t disappear once his friend reveals herself to be someone he may not completely recognize or understand at first. He works to understand. When explaining their upcoming trip to other SNL cast members, Steele mentions how the Ferrell knows she likes the “lowest, worst places” on the road. Ferrell helps Steele revisit these places while bearing witness to Steele’s deep well of self-hatred and fear.
These interactions are a testament to the thematic value of the road movie: connection amidst existential struggles; feeling at odds with the world while basking in its glory. Steele’s set of camping chairs become a motif throughout Will & Harper, signifying friendship during transitory moments and the value of stopping to appreciate what surrounds you. Toward the end of the film, seated side by side with Ferrell, Steele notes, “We’ve dropped these chairs in some very nice places, haven’t we?”
“I think sitting in the car and not getting out and feeling the air and feeling the people around you” is a waste of an experience, Steele told Little Village.
“I don’t necessarily set the chairs up in crowds, you know. I set the chairs up in parks or on the side of the road or some beautiful spot that I see and have a beer or something and sit for a while and meditate. So that’s what’s important about that. I do love them. I think when you see someone sitting in a chair, you want to talk to them, too.”
One destination that carries a complicated significance for Steele is her hometown of Iowa City, which the duo visited during filming. They stop to visit Steele’s sister, Eleanor, who expresses support for her sister’s coming out. This prompts Steele to share a memory from their youth in which Eleanor gifted her a pair of white frilly bellbottoms she didn’t want anymore. Steele recounts that it only took one outing in the pants before a friend slighted her as effeminate. She never wore them again.
“I grew up in thrift stores from when I was 18. Clothing is everything to me. I think people tend to think it’s superficial, but it’s a way of expressing yourself, like writing or any other expression,” Steele told Little Village. “I think it’s a way of trying to tell people who you are, who you wanna be. And I would agree when you come out first as trans, you’re wrestling with this person that you’ve been all along. But then, who is this person? Clothes do matter intensely for those moments. It’s not as superficial as people think. It’s, ‘Am I gonna wear androgynous clothes? Am I gonna wear very fem[inine] clothes?’ So you’re making these choices every day, and I’m still making them. I find I have people who wanna help me get dressed all the time, especially during this period of press, and I find that they’re not quite on the same wavelength as me. And what is that wavelength? It’s, ‘I wanna be my own queer self.’ And I find that I don’t know where I fall, and it’s an evolving process.”
While in her hometown, Steele takes Ferrell to visit her childhood house, serendipitously revisits her unicycling talents (in heels, no less), and reminiscences on her favorite picture of herself from her childhood. In it, she looks like the little girl she knew she was. It’s a tender moment, a reflection on the past, not solely filled with sadness but recognition. Euphoria captured on film.
Steele clearly still feels a tremendous amount of kinship with her hometown. In the film, she even muses on how she might retire here. Leaving the Midwest, especially for major cities in California or New York, can mean different things to different people. Some choose never to look back; others find fulfillment in returning to their small-town roots. But for Steele, it’s not as simple as that.
“I left Iowa so many times, [but] I never left Iowa,” Steele said. “It’s impossible; I don’t know how to explain that. It has a magnetic pull for me. It almost feels the same every time I leave. I have a pit in my stomach. I don’t like leaving. I also don’t like coming into the city, though, either. That also has a pit. It’s not an excitement; there’s a kind of, like, ‘Here I am again.’”
I left Iowa so many times, [but] I never left Iowa. It’s impossible; I don’t know how to explain that. It has a magnetic pull for me … I love Iowa City. I love it to death.
Harper Steele, on her homeTown
Interestingly, exactly halfway through the film, Steele and Farrell leave Iowa, continuing onward. It’s a subtle and profound editorial detail that prompts one to consider what leaving home feels like at varying stages of life and the elusive, paradoxical affection Steele and many others carry toward where they grew up.
“I love Iowa City. I love it to death,” she continued. “It’s just … there’s anxiety around it that probably stems from my earliest days of telling my parents that I’m gonna go hitchhike somewhere and seeing their nervousness. It’s always about 60 miles past Iowa City, once I leave, where the rubber band snaps, and I’m like, ‘OK, I’m loose now. I’m free.’ It’s almost like returning to your childhood, how much you enjoy that and then yet how much, you know, you can’t live there … I could live there forever, but I can’t.”
What is so remarkable about Steele’s introspection in the documentary is how quickly she reminds herself to give others the benefit of the doubt. Steele understands that there is plenty of hatred directed toward her and other LGBTQ+ people, but she also carries the self-awareness that much of her worry lies in her projections onto strangers.
If there’s one thing queer people and bigots have in common, it is fear. Those who fear come to hate, and Steele reveals the difficult truth that for most of her life, she feared and hated her true self deeply. Steele admits it’s difficult not to carry those lingering emotions into spaces, anticipating how unwelcome she will be made to feel. While it’s hardly uncommon for these suspicions to be confirmed, the film captures Steele’s surprise and attempt to learn that may not always be the case.
“My encounters with these people will change once I don’t hate myself,” she told me.
To hear a trans person articulate internalized hatred while taking accountability for their misjudgment of strangers is noble, yet haunting. None of this makes Steele any less angry and disappointed in anti-trans legislation, but it does keep her from being too cynical.
“Iowans are kind people. I grew up around kind people. Generally, we are neighborly; we are neighborly people. And I think that’s where we should all start with this. I think it’s inherent in the Midwest; I like to believe that, at least. I also think there’s a lot of fear of the unknown that sits in the Midwest as well. And right now Iowa is heading in a transgressive and wrong direction. This is not a direction that is Iowan to me, and I think people need to self-evaluate because we are friendlier people than what I’m seeing in that kinds of legislation and the kind of governance that’s running the state … I really would like to think that Iowa has a future of being a kinder state.”
Will & Harper is an earnest account of coming out later in life, a feat of vulnerability and bravery. That Steele was not only able to reconnect with one of her closest friends, but also use Will Ferrell’s success and kind curiosity as a means of regaining her footing in the world is a gift not only to the duo but those in the audience.
Will & Harper is currently playing at FilmScene and will be available to stream on Netflix Sept. 27.
