“Hey, here’s a weird one” was Harper Steele’s subject line in her coming out email to her longtime friend Will Ferrell. Ferrell revealed this tidbit at the Q&A of Will & Harper at Fantastic Fest, both stars laughing as Will explained how well this represented Harper’s bizarre and brilliant sense of humor. We’re all very familiar with the ostentatious oeuvre of Will Ferrell – he’s been a staple of numerous, diverse comedic endeavors since his days at Saturday Night Live. But in Josh Greenbaum’s (Barb & Star Go to Vista Del Mar) latest documentary, Will eagerly acquaints us with one of his closest friends and comedic inspirations, Harper Steele, as she is introduced and reintroduced to the world as a woman. Coming out of the fog of the early days of the pandemic, and coming out of the closet to the world, Harper is invited to go on a road trip across America with Will – to reconnect, reminisce, and boldly go where no comedy legends have gone before.
Will & Harper begins in a harsh, icy New York City Winter, where Harper still has the gusto to put on a cute dress and a pair of heels before she picks up her friend Will. The two besties reunite and make a quick stop to 30 Rockefeller Plaza, where they meet up with some of their fellow SNL alumni to have the first of many hilarious, eye-opening conversations. The film features cameos from several SNL favorites from Will and Harper’s era like Seth Meyers, Tina Fey, Tim Meadows, Paula Pell, Molly Shannon, Will Forte, Kristen Wiig – all of whom contribute something meaningful to this journey. From the moment Harper and Will met at SNL, they knew their friendship was special. Will explains, every bewilderingly bonkers career move he’s made has been thanks to Harper. She’s always been confident in her kookiness and is responsible for such cinematic gems as The Ladies Man, Casa de mi Padre, Eurovision Song Contest: The Story of Fire Saga, and a Lifetime original movie called A Deadly Adoption. But when it came to her gender identity, Harper was far less confident, and lived in quiet despair for decades.
Throughout the course of the film, Will and Harper take turns driving, and take turns sharing their perspectives. And as severely funny as both of these people are, they’re prepared to have challenging, sometimes uncomfortable conversations. Prior to her transition, Harper would often take solo-road trips across the country, and always had an affinity for the dingiest dive bars our 50 states have to offer. Now, as a sixty-year old trans woman, Harper wonders if these same, beloved, seedy establishments will still welcome her business. Thankfully, Harper has the great, famous, household-name known as Will Ferrell to accompany her, as a way of disarming or even distracting the potentially-trepidatious masses from her otherness. It’s immensely frustrating to witness Harper being misgendered, disrespected, and gawked at, but her buddy Will is always there by her side to provide any support he can. Ferrell is used as a powerful tool in Will & Harper, as a curious and determined student to Steele’s tutelage, and as a surrogate for the audience watching, who may be just as curious and uninformed.
The two friends discuss a plethora of topics pertaining to trans existence, from the increasingly violent anti-trans legislation persisting in America, to the odd experience of performing gender in general. Our world is so annoyingly, oppressively binary, and femmes especially are scrutinized for the ways in which we perform femininity. Harper explains the strange, nuanced experience of now regularly-applying makeup, and how it can simultaneously affirm her desires to be hyper-feminine, and expose the aesthetic work that she perceives to be unfinished. She also details the profound dysphoria of performing masculinity for so many years – a painful sentiment that is shared by another trans woman, Dana Garber who they meet on the road. Throughout these tough conversations, Harper is radiantly resolute, and Will is there to listen, learn, and ask the occasionally stupid, funny question like, “Do you think you’re a worse driver now?”
On the surface, Will Ferrell’s presence in this film could seem like a classic case of a white, cisgendered man forcing himself into a space that is not his. But Ferrell acts as a gateway to acceptance for many of the country and city folk they meet along the way, and this power extends itself beyond the parameters of the big screen. Will & Harper is streaming on Netflix – a popular streaming service that many people, even of a certain, perhaps intolerant age, can access. I’d like to think that this documentary will be seen by a vast number of people, and that even those with a closed mind can be convinced to open their hearts. It feels impossible to not be charmed by Will & Harper – a documentary that operates in humor, heart, and hard truths. And as I observed each breakdown and breakthrough on this friend’s road trip, I found myself hopeful for humanity for the first time in quite a while.
The entire experience of watching Will & Harper feels like a warm, comforting hug and a giant sigh of relief. Will invites Harper to share her story in her own words, and Harper allows Will to be a bit sloppy in his quest for understanding. This documentary is a lesson in empathy, compassion, and true, unwavering friendship. The buddy road trip movie has been covered countless times, but Will & Harper offers so much more than just a fun soundtrack and roadside hijinks. It proves that no matter how old you are, where you come from, or how you express yourself, it is never too late to learn and grow and be kind. Life is short, and our country is intolerant, but people are people, and we all deserve the chance to be understood and accepted. Being an ally to the trans community has never been more important, and I salute these goofy icons for demonstrating how much mileage we can get out of being there for our friends.
