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Will Ferrell’s road-trip doc could be the biggest in Sundance history

by Staff

PARK CITY, Utah — Will Ferrell remembers the email well, with the subject line, “Here’s a Weird One.” It came from his dear friend, Harper Steele, who had been hired as a writer on “Saturday Night Live” the same week that Ferrell had been named to the cast, and who collaborated on some of Ferrell’s most famous sketches. And now Steele was writing to say that it was time, at 61, to stop hiding and begin living as a woman. Steele would be using she/her pronouns but hadn’t yet settled on a name, and was hoping for understanding from family and friends on what would surely be a slow and awkward and terrifying and joyous journey.

“Instead of an a——, I’ll be a b—-,” Steele wrote, in the letter that Ferrell reads aloud, chuckling, in the new documentary “Will & Harper” — which premiered Monday at the Sundance Film Festival to multiple, explosive standing ovations. If rumors are true, Apple TV Plus has been circling and could make it the biggest documentary sale in Sundance history, even bigger than “Boys State,” which sold to Apple and A24 in 2020 for a record $12 million.

Steele has always loved a road trip, showing up to small towns in the middle of nowhere America, and it was Ferrell’s idea that they embark on one together, on film. It would give the comedian a chance to reacquaint himself with his friend of 30 years and to ask all the impertinent questions he wanted to ask, such as what made her transition, and does she still like terrible beer? (Old Milwaukee is Harper’s champagne of brews.) And it was also a way to provide support for Harper as she reentered places she once loved to go, like dive bars and Midwest dirt-racing tracks, in a new body, with excitement and insecurity about how she had be seen, and a deep sadness for how long she had taken to come out, and concern for her physical safety in parts of the country where she never had to think about such things before. “I know I love America,” Steele says in the documentary. “I don’t know if it loves me.”

What follows is a movie that’s so sweet and funny, so generous and gentle about explaining trans-ness to older generations, that it feels like it should be shown in schools and toured around the country as a vital, lifesaving tool.

When the two friends first met, no one on SNL quite knew what to do with Ferrell’s weird energy. “They thought Will Ferrell was a dud,” Steele says in the film. But the two of them had an immediate kinship. In the film, they meet up with their SNL family along the way, such as Tina Fey, Seth Meyers, Tim Meadows, Will Forte and Molly Shannon. Calling up Kristen Wiig to check in on the theme song they asked her to write for them becomes a running gag. (“Harper and Will go West / Just a couple old friends and a couple of brand new breasts …”)

In between the many jokes and bits, though, are poignant moments in which Steele opens up about the shame and the pain she’s been feeling for so many years, and the many other road trips she took across the country while wearing a dress in her car, only to have to change back into men’s clothes whenever she stopped for gas or the bathroom, out of fear of being found out. Ferrell is comic relief and a catalyst for conversation, but a lot of times he’s just listening and trying to understand. “I felt like we were going to be a part of this and treat it with integrity, and that I owed it to Harper to be open and emotionally available to whatever was going to happen,” he said in the Q&A.

But that doesn’t stop him from making plenty of crass jokes (that Steele finds very funny), such as, “Do you think you’re a worse driver now that you’re a female driver?” or “Did you go to Nordstrom Rack more when you got your new rack?”

And somehow within all this is a heartening portrait of America. There are bad moments, such as when they unknowingly take a picture with a politician who had just signed an anti-trans bill, or a time when Ferrell’s celebrity and instinct to be a ham puts Steele dangerously on display (Ferrell cries in the car the next day, feeling like he’s failed his friend). But there are also many more moments that give you hope in humanity, like when Steele makes a trepidatious first solo trip into a dive bar in Oklahoma with a “F— Biden” sign on the wall and gets welcomed by a tableful of new friends.

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During filming, director Josh Greenbaum said, they had decided to just let the two friends riff off one another; the only real plan was when Steele mapped out the places they would go. They wound up with 215 hours of footage, but gags such as Ferrell eating from “puddle bunny,” a chocolate bunny that melted on their dash, only made the end credits.

What did make it into the film was a moment when Steele gets into a hotel pool in a bathing suit, and Ferrell, as a show of support, breaks out a Speedo from his extensive collection to support her. “I thought, ‘Well, Harper’s taking a big risk of swimming in a bikini here for the first time,’” Ferrell said. “But when I watched it on film, I took a bigger risk. She looks elegant and sporty, and I look like an endangered sea mammal.”

At the forefront of their minds, though, was always the kind of impact a film like this could have. It took Steele two to three months to say yes, but she felt galvanized watching anti-trans bills get passed all over the country. “It is still quite awful. It’s ramping up. And I have this friend who has made movies that appeal very broadly to a lot of people. That was the deciding factor, like, ‘Oh, I can abuse this relationship for the good!’” Steele said, laughing.

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