How 'Will & Harper' Stuck Its Impossible Landing

“It’s okay to feel pretty and do nice, pretty things for yourself.”

Up in a hot air balloon in Albuquerque, New Mexico, actors Will Ferrell and Will Forte are floating high in the sky. They’re with their friend, writer Harper Steele. “It’s pretty high,” Forte comments. “Wait, hold on, hold on,” Ferrell interrupts. “What is it?” Forte asks. “Do you guys hear those dogs down there?” Steele acknowledges the faint sound of a dog barking far in the distance. “Quiet!” Ferrell screams down at the dog. “Shut your dog up! Shut your damn dog up! The neighborhood is sick and tired of your dog!” More dogs begin barking as Steele and Forte chuckle at their friend with the kind of expressions on their face that can only come from knowing, really knowing, a person, and loving, really loving, their quirks.

See, it’s easy when describing Josh Greenbaum’s skillful Will & Harper to talk about the gut wrenching scenes or the happy tear-inducing ones or the ones that crack open a faith in humanity you maybe thought you’d lost, but part of what makes this documentary sing — and I’m talking Lauryn Hill in Sister Act 2 sing! — is the small, innocuous moments that underscore the big ones, like watching Harper, who came out as a trans woman two years before the events of the film at the age of 61, rediscover riding the unicycle, or watching the pair do synchronized cannonballs, or witnessing them coronate their beers while sitting in folding chairs overlooking the Grand Canyon (“Cornelius Danderhoff,” Ferrell reveals matter of factly, to which Steele responds: “This is Dolores O’Brien. I’m gonna drink her all up.”)

Ferrell and Steele have the kind of ease in their friendship rarely depicted on screen. They don’t finish each other’s sentences, nor telegraph a lifetime of memories. They don’t say “I love you” or seem overly-affectionate. It’s the little things. They look each other in the eyes, rub each other’s shoulders and seize on every opportunity to chide the other.

17 days is a long time. It’s a long time to be away from family, away from work, away from your creature comforts. It’s also a long time to spend consecutively with anyone, no matter the relationship, and on the road, no less. That premise for this documentary, now on Netflix, creates the necessary tension that’s not “Will they…?” but rather “How will they…?” It gives the film a framework to tell its story that feels narratively cohesive, while also allowing for discovery. 

It looks amazing (shout-out to cinematographer Zoë White) and sounds that way too thanks to a boastful soundtrack: “Amoreena” – Elton John, “Long Road Ahead” – Jim Ford, “Wildflowers” – Tom Petty, “Shelter From the Storm” – Bob Dylan, “Long Gone Lonesome Blues” – Hank Williams, “America” – First Aid Kit, “Beep Beep (The Roadrunner)” – Don Ables, “Ooh Las Vegas (feat. Emmylou Harris)” – Gram Parsons, “Holocene” – Bon Iver, “Go With Me” – Gene & Debbe and so many more. And that’s not even mentioning its best needle drop (more on that in just a second).

“How you feeling?” Ferrell asks Steele as they embark on their cross-country roadtrip in Steele’s Grand Wagoneer. “I feel good,” Steele replies. “Well, there’s no turning back now, so…” Ferrell tells her. “Oh, okay,” she responds. Then: “Oh, geez.” They both chuckle. It’s something they do a lot. For instance, at the trip’s conclusion, they’re back in their beloved folding chairs on the beach when Ferrell surprises Steele with a pair of diamond earrings. “It’s okay to feel pretty and do nice, pretty things for yourself,” he tells her. “Oh, geez,” she says, echoing their back and forth at the trip’s outset. Visibly emotional, she chuckles, lost for words. “It’s just so cool. It’s just so sweet.” That summarizes, quite perfectly, this film. In fact, its subject goes to great lengths to never be saccharine or overly-sentimental; rather, it’s simply — but never simply — sweet.

This is easily the best film of the year, and I say that acknowledging that a quarter of the year is yet to take place. It’s so gentle and yet so confident in its storytelling. It would be easy to call this film life-affirming, but that implies that it reinforced a held truth, and I think this film does more than that. I think it digs deep into some decaying roots and attempts, with remarkable aptitude, to fortify them. That it provides what will very likely win the Academy Award for Best Original Song courtesy of [checks notes] Kristen Wiig is yet another example of the surprise and delight around every turn of this far-ranging film, which I believe has earned the categorization of instant masterpiece.

We meet Steele years into her declaration of womanhood, but it's her desire — her need, as she describes it — to be seen as such that anchors her journey. “I’m not sure… It’s just they may not see me that way,” she tells Ferrell, referring to the kind of folks she’s spent years chumming it up with at bars.

“This is an odd thing to say: I may not see myself that way. But you sort of running point makes this a fuck-lot easier than if I was just alone.”

Ferrell is an unyielding support system throughout, waiting outside when she needs to go it alone, ready to spring into action if needed. He also fucks up, causing her discomfort unbeknownst to him. It’s uncomfortable for all. He cries. She comforts him. At other moments, she cries. He comforts her.

“So many of us don't know what the rules of engagement are,” he tells her early on in their journey. She welcomes every question, in some instances yearning for him to ask so that the lingering uncertainty dissipates. And it does.

On Sunday, I posted a meme from the film on Instagram. The pair are visiting a woman named Dana Garber in Peoria, Illinois. She shares with Harper her own experience of coming out and the decision to not alter her voice due to society’s conception of what a woman should sound like.

One of my followers commented the following:

“This was a beautiful film. Seeing Harper slowly relax around Will as the days passed made me realize how tense I started out watching it, wondering if he was going to be insensitive, making jokes that were off color or invalidating her feelings. I shouldn’t have gone into it with such a preconception.”

I felt the same way, too. Even though I was assured that this would be an ultimately feel-good film, I found myself internalizing the discomfort of a friendship out of its groove at the film’s outset. And though Ferrell’s intentions are clearly in the right place, you can’t help but brace yourself for some discomfort. And it comes, in big ways and in small, from innocent misgendering to being called a creature by online trolls. 

“I really feel for Steele’s vulnerability, as much as I cringe at the numerous times Ferrell does something to her that you’re never supposed to do to a trans woman,” The Guardian’s Veronica Esposito wrote in her review, adding that she “longed for [Steele] to set some boundaries.” But I think that very thought pattern — what you’re never supposed to do — is what this film is seeking to at best unpack and at most dismantle. Sure, asking questions about whether a trans person hopes to have gender-affirming surgery is incredibly invasive. But within the cocoon of their friendship, and with a boundary set by Steele, it allows for an honest and forthright conversation. I don’t think the film is purporting to suggest asking this to the next trans person you meet. Instead, I think it’s recognizing a curiosity that many cis folks have about trans people and allowing it to be a discussion as opposed to an inquisition.

It can be easy, given the current state of men in the public eye, to grow weary of the species. Diddy. Elon Musk. Johnny Depp. JD Vance. Russell Brand. Dr. Luke. Vince McMahon. Danny Masteron. Bill Cosby. Kevin Spacey. And while they don’t embody all men, you can’t help but come up remarkably short when trying to make a list of wearisome women. But Will Ferrell marks a good argument in favor of men’s right to exist. Ferrell is not just in the role of co-captain, but also repeller and anchor. He comes to this project with a pureness of intent: He loves his friend and wants to figure out the best way he can show her that love, which he understands is something he’ll have to learn from her vs. intuit. He’s willing to learn. In fact, so much of this movie is Ferrell listening: Listening to Harper, her sister, her kids, Dana Garber and the retired therapist at the Grand Canyon. 

This movie is very much about Harper Steele, but it’s also very much about Will Ferrell, a celebrity who I would wager is often conflated with the characters he’s played. I know I kinda did. I don’t think you come away from this film with a deep understanding of Will Ferrell. I don’t think that’s the point. But I do think you come away with a deep understanding of the kind of friend Will Ferrell is. And I think, at least for me, it makes me think about the kind of friend I am. The kind of friend I want to be. Similarly, as much as Steele reveals, especially in the final stretch of the film when they visit her secret property in Trona, California, she also doesn’t offer up a fully rendered version of herself. (Remember, her goal is to be seen, not known.) In that sense, and upon greater reflection, it’s a film more about the center of the pair’s Venn diagram than I had first thought.

In an essay I wrote earlier this month, “Will Ferrell, Harper Steele and Art's Role In Creating Social Change,” I considered the question many are asking about this film: “Can it save lives?” Having not yet seen the film at the time, I reasoned:

“A cynical answer might be an immediate ‘no,’ while a quixotic one might reason ‘of course.’ For me, I’d position this akin to Peter Pan’s ‘I do believe in fairies’ in opting to choose to believe in the power of a film like this. I recognize the platform’s reach, the storyteller’s reach and a framework that feels fresh. I think being honest about the discomfort and growing pains human beings feel when faced with change of any kind is important to spotlight. We’ve grown accustomed to shaming people for their belief systems rather than attempting to understand where those belief systems are born from and, more importantly, if they can be unlearned.”

Having now watched the film, I felt a similar way watching Steele well up with emotion at the film’s end as I did watching Gus Walz stare up at his father at the Democratic National Convention. It was pure, unbridled emotion brought on by loving a person who loves you. Steele’s journey to loving herself without fear or judgment and being seen, really seen, by others, will be ongoing and certainly not solved by putting thousands of miles on her pedometer. But Ferrell sees her. He affirms her. And he’s no doubt helped her by simply doing something that comes naturally to him: loving her.

That’s something I think this film captures so poignantly. As Ferrell and Steele get pedicures with Molly Shannon in the waning moments of the film, Shannon asks if there’s anything Steele learned about Ferrell that she didn’t know.

“Um… what I really learned about Will… Like, we’ve been friends for 27 years, y’know? But… Yeah. I mean, he loves me. You know what I mean?”