Will & Harper is a revelatory road-trip movie and an unassuming political project | Canada Voices

There’s an illuminating scene in Josh Greenbaum’s new documentary Will & Harper where the director’s titular subjects, former Saturday Night Live head writer Harper Steele and star Will Ferrell, sit across from each other in a swanky Las Vegas restaurant. Long-time friends ever since they both began working at SNL in 1995, the pair have decided to paint the town red.

The only problem is that, while Harper is radiant in a simple, yet tasteful black dress and matching heels, Will – continuing a decades-long bit between the friends wherein each of them try to make the other laugh by showing up in costume unannounced – is no longer Will. He is, instead, the man now known as David Abernathy.

Decked out in a loudly patterned bomber jacket and ominous gold amulet, Will a.k.a. David has topped off his bizarre ensemble with a short, dark brown bobbed wig, gaudy wrap-around sunglasses, and a Fu Manchu mustache in an attempt to go out into the world incognito. The gag is initially appreciated by Harper, who is equally aghast and enchanted by the deranged look, but as the friends continue their night out, the stark reality of how each of them moves through public space quickly soon breaks the humorous spell.

It’s a revelatory moment that arrives at the beginning of the end of the duo’s cross-country road trip, a journey which began in 2022 when Harper, a lifelong lover of road trips and all things Americana, came out to her loved ones as a trans woman at the age of 61. “Will responded quickly, appropriately, and with love,” Harper says during an interview ahead of the film’s premiere at the Toronto International Film festival.

In the wake of this hugely transformative moment for the former Funny or Die creative director, the idea of filming herself and Ferrell taking part in a road trip from New York to Los Angeles took Harper some time to adapt to.

“I don’t like being on camera – I’m less nervous, obviously, about it now; but at the time, I really didn’t want to do it,” the Iowa-born-and-raised Harper shares. “I had to come around to the idea. I really ruminated on the possibilities of what it could do – not just for me personally, but for so many other trans people. And Will is a great vector for that work having [non-trans people] come to understand our issues.”

“Also,” Ferrell chimes in, “we were hoping to stop at a lot of waffle houses.”

Just as they do in Will & Harper, Steele and Ferrell spend much of their interview time together jumping from serious discussion to playful banter, a shared trait that Greenbaum says was a key development in their relationship during filming.

“Early on in the filming process, if ever things got too uncomfortable for them, they would fill that uncomfortable silence with jokes – as comedians, their love language is comedy,” he says. “So at one point, I had to pull them both aside and give them my greatest tip as a documentarian, which is to ask a question and then shut up and listen.”

That ability to remain both curious and vulnerable is what underscores both the spirit and impact of the conversations that Steele and Ferrell have on screen.

“Harper was so clear about welcoming any question,” says Ferrell. “She made me feel safe to bumble and stumble around and have any sort of dialogue that I wanted to broach. That took the pressure off, in a way. The only negative thing that comes to mind when I watch the movie back is that night out in Vegas where I concocted that ridiculous outfit. That’s the one moment where I thought, ‘Maybe this is too much?’”

It’s a sobering moment where Will’s commitment to the bit brings unintended attention to Harper who, as a clockable trans woman, is often made to endure the urgent reality of gendered violence that comes with such hypervisibility. Without fail, Ferrell’s disguise is so over the top that it only works to further out his celebrity presence in the restaurant, a fact which results in an onslaught of transphobic tweets targeting Steele.

Indeed, many of the film’s most poignant scenes witness the ways that Will and Harper are circumscribed in various social spaces, from dive bars to basketball games to small town diners. Prior to coming out, Harper had journeyed across America hundreds of times, but, with Will & Harper, she took part in her first ever road trip after transitioning.

“I was very conscious of that reality of Harper’s experience – that constant threat assessment. Sometimes it’s louder, sometimes it’s quieter, but it’s always there,” Greenbaum says. “I realized that I was taking for granted the safety of what, to me, were very normal, neutral spaces. It was illuminating for both me and Will.”

Referring back to Will’s Vegas gaffe, Harper emphasizes, “It was funny. There’s this perception that all trans people are strident and angry that completely ignores all of the joyful aspects of being trans. I’m hoping the movie conveys that reality. Absolutely, I can be strident, but I’m still gonna be funny.”

Balancing those tonal truths during a road trip which included several stops in conservative states – including those with current anti-trans legislation and even encounters with the very governors at their helm – is no small feat.

“One thing we came to understand with this film,” Greenbaum says, “is the reality of the truism, ‘It’s hard to hate up close.’ Harper and I were both pleasantly surprised that we were met by people across America with, at best, love, and, at worst, apathy, which – considering the very real dangers that trans women face – is not all that bad. That said, we can’t be Pollyanna-ish about it – there’s still a lot of work to be done.”

Greenbaum’s sentiments speak well to the graceful and tender nature of Will & Harper and its unassuming political project. Its heart, no doubt, lies not just in Ferrell’s high-profile allyship, but also undoubtedly in Steele’s ability to disarm viewers with her pointed wit and down-to-earth approach to the world around her.

“It’s almost like therapy,” she says. “It’s an unfolding. The goalposts for comfort change as you move further into the process – I probably wasn’t as forthcoming at the beginning of filming as I was as we went on. In general, after having come out, I feel like I don’t really have any secrets anymore.”

Will interjects, offering, “You carried a steamer trunk with your secrets in it with you for so long.”

Nodding in agreement, Harper adds, “I think everyone likes to hold onto those things that they’re uncomfortable with or that they’re afraid of. But once Will and I committed ourselves to being honest about those things, we were completely in.”

Will & Harper is available to stream on Netflix starting Sept. 27.