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In the Funny, Earnest ‘Will & Harper,’ Will Ferrell Navigates a Friendship In Transition

In 1995, on their first day working together at Saturday Night Live, Will Ferrell knew he’d get along with Harper Steele. A green actor and an inexperienced writer, they shared a similar sense of humor and penchant for physical comedy, traits that quickly developed into a meaningful friendship. Steele, who later took over as the show’s head writer for four seasons, championed Ferrell during his first year and wrote to his strengths and antics, a skill she continued to exercise when she joined Ferrell and Adam McKay’s production wing Funny or Die in 2008. Since then, some of the wackiest projects that the Hollywood A-lister has produced and starred in—the Spanish-language melodrama Casa De Mi Padre, the Lifetime TV movie A Deadly Adoption, and Eurovision: The Story of Fire Saga—have sprung from Steele’s absurdist creative mind.

A couple years ago, however, she wrote something that Ferrell wasn’t prepared to read.

“I’m old now,” Steele said in an email. “I’ll be transitioning to live as a woman.”

Both Ferrell and Steele re-read this letter at the start of Will & Harper, a new film from director Josh Greenbaum, which follows the pair of best friends on a 16-day road trip across the country as they process Steele’s transition, reconnect as friends, and see America through the eyes of a trans person. The documentary, which premiered Monday night at the Sundance Film Festival to instant and rapturous applause, feels like a joyous and welcome surprise. At a time when trans rights continue to be under attack, this indelible and funny portrait of friendship doubles as an earnest, vulnerable, and open-hearted response, a crowd-pleasing tonic and a bipartisan bridge to empathy and understanding. If the reactions in Park City are any indication, it seems primed for serious success.

Before transitioning at the age of 61, Steele wore her Iowa-born, light-beer-drinking pride on her sleeve. As Ferrell remembers, she’d always had a keen love for dive bars, back alleys, and grimy diners, and spent a lot of time driving through overlooked parts of the country whose politics and attitudes didn’t line up with her own. Since her transition, she’s kept those interests and her humor (“Instead of an asshole, I’ll be a bitch,” she wrote jokingly in her coming-out email), but with her new identity and appearance, Steele can’t help but wonder how the communities and towns she’d grown up around would welcome her back. “I don’t know if I can go to those same places as Harper,” she says. “Will I still be loved?”

The impetus for taking Steele’s Grand Wagoneer from New York to Los Angeles came from Ferrell’s interest in watching his best friend experience the road for the first time as Harper. But it also stemmed from the actor’s own naivete about transgender people. As he admitted this week, before Steele came out to him, Ferrell didn’t have any close trans friends. In addition to spending a couple weeks catching up with his old pal, he felt it might be a golden opportunity to pepper Steele with basic and complicated questions that most people never feel comfortable asking. What are her biggest fears about the trip? How does she handle high heels? And a crude laugh line: Is she a bad driver now?

As excursions with a pair of comedians tend to go, Will & Harper is filled with those kinds of friendly jabs and jokes. Near the beginning of their trip, Steele unironically purchases numerous cans of flavored Pringles before the pair sets up folding chairs in the middle of a Wal-Mart parking lot to eat them. Their transportable furniture becomes a running gag, in which they plop down in random places to enjoy the beauty of their ordinary and extraordinary views. Along the way, Ferrell whines when Steele refuses to stop at Dunkin’ Donuts, disguises himself in a ludicrous getup for a fancy Las Vegas dinner, and yells angrily at barking dogs from the perch of a hot-air balloon. Though his humor sometimes masks some awkward moments, it’s more often a safety valve and resource when the mood dips or the tension spikes.

Greenbaum, who recently directed the comedies Barb and Star Go to Vista Del Mar and Strays, has a good sense of rhythm and pacing, knowing when to let Ferrell and Steele get vulnerable with each other. To their credit, the conversations never feel too forced, and the more they open up, the more both friends ease into their redefined relationship. Though Steele had known her transition was a long time coming, it was frequently interrupted by therapists uninterested in guiding her to embrace that kind of change, she says. It leads Ferrell to ask about breast surgery, and whether she’s struggled with body dysmorphia. “Every time I’ve done something for myself, it’s been guns blazing,” Steele says. Another day, she remembers the depressive thoughts that made her scared to keep a gun in the house. After her transition, though, “all I wanted to do was live,” she says.

Will & Harper doesn’t dive too deeply into politics. The closest it comes is during a Pacers game, where Ferrell and Steele sit courtside and briefly speak with Indiana’s governor. The next day, they realize that he—like many other state leaders—had recently signed a statewide gender-affirming care ban, and Ferell laments not pressing him about it. Still, if it feels like the road trip has too many sanded edges, or that it’s painting too palatable a picture of strangers accepting Steele in various social settings, the pair do encounter adversity during a pit stop at a Texas steakhouse. When Ferrell walks in, ready to devour an enormous steak while dressed as Sherlock Holmes, he’s greeted by hordes of gawking restaurant-goers recording him and Steele with their phones. The next day, Steele reads through a host of vicious and transphobic social media posts, prompting Ferrell to get emotional. “I feel like I let you down at that moment,” he says through tears.

It’s one of the few times that Ferrell’s celebrity doesn’t shield Steele from online and verbal attacks. The documentary is aware that the presence of a celebrity companion doesn’t always make for an honest representation of the treatment directed toward transgender people. But Ferrell’s presence is just as easily an example of how important allyship can be. At a diner, he gently corrects a waitress addressing Steele as “sir.” And when Steele wants to enter a seedy Oklahoma dive bar—plastered with Trump and confederate flags—by herself, Ferrell waits in the parking lot, waiting to spring inside if necessary.

There’s nothing too inventive about Greenbaum’s structure and aesthetic. While his subjects drive over highways and dirt roads, he supplements his footage with lighthearted montages and mainstream needle drops—he samples Brenton Wood, Bob Dylan, Tom Petty, and Frank Sinatra—and even sources an end-credits original from Kristen Wiig. Everything feels a bit conventional and accessible—which is the whole point. A road-trip documentary like this is really just the starting point of a much longer journey of understanding and acceptance. It’s an icebreaker—for its subjects, and for everyone watching. As the pair of friends depart from the California coastline, Ferrell acknowledges that once the cameras stop rolling he’ll probably have even more questions for Steele. “I’m going to think of something to ask you tomorrow,” he says. Then he takes a beat. “But we have time.”

Originally Appeared on GQ