A Will Ferrell Road Trip Documentary

This review was published on January 23, 2024, out of the Sundance Film Festival. Will & Harper is now on Netflix.

One of the most ecstatic responses I’ve ever seen at Sundance came at the world premiere of the documentary Will & Harper, Josh Greenbaum’s film about a cross-country road trip taken by Will Ferrell and his trans best friend Harper Steele. Warm receptions are often guaranteed for movie stars and progressive causes at Sundance, but one can usually tell when the applause is dutiful and when it’s genuine. In this case, the standing ovation was immediate and explosive. The festival audience clearly ate this one up, in part because Will & Harper also happens to be a very funny movie about two comedians stuck on a road trip together.

Ferrell and Steele both started at the same time on Saturday Night Live in the 1990s — one as an actor, the other as a writer — long before Steele transitioned at the age of 61. Steele quickly became someone who could write best to Ferrell’s strengths (she remembers that in Ferrell’s first season many on the SNL staff didn’t find him funny) and was later named head writer of the show, before departing in 2008 to work for Ferrell’s comedy outlet Funny or Die. (She also wrote or co-wrote several of the actor’s films, including my beloved Eurovision: The Story of Fire Saga.) As Ferrell tells it, the Iowa-born Steele was something of a tough guy at the time, someone who loved drinking “shitty beer” and hitch-hiking and road tripping across the country. And while Harper acknowledges that “there was this other persona that I don’t much like anymore,” she also insists she hasn’t changed that much. “I was always Harper Steele,” she says. “Will was always friends with Harper Steele.” And the old shit-kicker hasn’t entirely gone away. “Instead of an asshole, I’ll be a bitch,” she quips.

The idea for the documentary grew out of Ferrell’s desire to accompany Steele on her first trip across the country after transitioning. She still loves country roads and dive bars and highway diners. “I just don’t know if it loves me back now,” she admits. “I don’t know if I can go to those same places as Harper.” These kinds of serious insights are often accompanied by funnier observations. “When I road tripped as a guy, I brought two T-shirts, three underwears, and one pair of jeans,” Steele says. Things have changed, she notes, as the camera cuts to an entire suitcase full of women’s shoes. Early in the film, talking to Steele’s kids about whether they fear for her safety out on the road, Ferrell asks, “Does it help that I do jujitsu? I go twice a month.”

Greenbaum, who directed 2021’s Barb & Star Go to Vista del Mar and last year’s Strays, clearly has a feel for buddy comedies and road movies. There are repeated bits involving the many different varieties of Pringles, and Will Ferrell’s petulant desire to eat at Dunkin’ Donuts. Their old SNL chums show up at a few points. They make a point of giving Lorne Michaels an uncomfortably long hug. They ask Kristen Wiig to compose a theme song for them: “Something up-tempo, jazzy and fun, but it also has to make you cry, and with a little twang.” They then spend the rest of the movie trying to get her back on the phone.

Their itinerary is designed to let Steele re-experience a world she used to know so well. At a Pacers game, she notes that she was once another member of the army of bros in the stands. She says she doesn’t know how those folks will see her now, but she also adds that she doesn’t know how she’ll see herself. Later, as Steele enters an Oklahoma bar festooned with Trump signs and Confederate flags, Ferrell waits outside, ready to pounce if the situation gets dangerous. Lo and behold, the crowded bar quickly embraces Harper Steele. They’re all toasting each other and doing shots by the time Ferrell joins them, leading to a whole host of double takes. “The joke’s on me,” Steele says afterward. “I’m not afraid of these people. I’m afraid of being myself.”

The conversations the two have on their trip are admirably frank. They talk about top and bottom surgery, misgendering, body dysmorphia, and the fears Harper had before coming out. These exchanges never feel staged, or obligatory. Steele tells Ferrell that he’s free to ask her all the things that he might otherwise be afraid to ask a trans person, and Ferell does so, clumsily but sweetly. But he also seems genuinely terrified to learn that his best friend for all these years was in so much pain that she was contemplating suicide. The film’s most powerful achievement is perhaps also its most basic: the simple sight of two friends talking, openly and gently, about all the things on their minds.

Steele admits she has a lot of privilege, and that having a good friend like Ferrell accompanying her on this trip is one of them. He attracts more attention than she does, although this does backfire at one point in Texas, when he attempts to eat a massive steak dressed as Sherlock Holmes (don’t ask) and they suddenly find dozens of cellphones creepily pointed at them. The incident also leads to news reports and torrents of grossly cruel transphobic tweets hurled in their direction.

While the film mostly presents ordinary people as accepting, tolerant, and non-judgmental, it does acknowledge the dangers that trans people regularly face. At the Pacers game, Ferrell chats with Indiana governor Eric Holcomb, who seems polite enough when the actor explains that he’s accompanying his friend on her first road-trip post-transition. Later, they look up Holcomb online and discover that the governor has signed a law banning gender-affirming care. It’s just one rebuke in a litany of ongoing cases around the country. Indeed, just three days before Park City itself cheered on Will & Harper, the Utah State Legislature passed an anti-trans bathroom law.

Will & Harper is in many senses a very conventional picture. The soundtrack accompanying them on their trip is pretty on-the-nose. “Shelter From the Storm,” “America,” “The Weight,” and “Truck Drivin’ Son of a Gun” all make appearances, as does “Luck Be a Lady Tonight” for the obligatory Vegas interlude. At their post-screening Q&A, Steele and Ferrell recalled that when they first decided to do the film, they tried to think of comic set-ups and situations in advance, before realizing that the best way to approach such a project was just to let events take their course. But the duo’s journey does have a recognizable narrative shape, leading toward a not-entirely unexpected emotional climax. The film’s familiarity may well be part of its design. It clearly wants to help change hearts and minds, and find purchase with audiences that would otherwise avoid a movie with a subject like this. Judging by the rapturous Sundance response, it has a decent shot.

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