'Will & Harper' Review: Will Ferrell's Trans Road Trip Doc Will Save Lives – The Daily Beast

When his friend of 30 years came out as transgender, Ferrell suggested they drive across the country together. “Will & Harper” is the sensational documentary about that journey.
Senior Editor, Obsessed
PARK CITY, Utah—Will Ferrell and his dear friend Harper Steele began working at Saturday Night Live the same season, nearly 30 years ago.
Ferrell was cast as a performer, and Steele was hired as a writer. The early buzz on Ferrell was that he was a “dud,” Steele says. But Steele understood the now-SNL legend’s peculiar gifts, writing many of Ferrell’s most famous sketches, the beginning of a creative partnership and deep friendship that has lasted decades and bled over into Ferrell’s movie career. The most ridiculous, head-scratching projects he’s acted in, Ferrell says—an Icelandic pop star in Eurovision Song Contest; Lifetime movie A Deadly Adoption; Casa de mi padre, a comedy that is entirely in Spanish—Steele was behind.
It’s their penchant for collaborating on surprising, out-of-left-field projects that took the friends to the Sundance Film Festival, where Will & Harper had its world premiere Monday night. The screening was soundtracked by an audience duet of roof-shaking laughter and silent, moved sobs—culminating in multiple standing ovations that left the Anchorman star wiping away his own tears on stage. It’s common to feel a certain electricity when a film plays well at a festival. What happened in the auditorium Monday night felt more like a kinetic warmth, as if loveliness could be somehow tangible.
It’s not just that the project is brave and characteristically unusual. It’s that—and please do your best to strip this upcoming phrase from all of its corny, eye-rolling earnestness—the film is an endeavor that could change and even save lives.
Ferrell and Steele hadn’t seen each other in a while because of COVID when, three summers ago, Steele wrote Ferrell an email with the subject line: “Here’s a Weird One.” In the email, Steele explained that she would be transitioning, identified as a transgender woman, and will now be going by Harper. She explained that it was something she’d felt needed to do for a long time, expressed the mixture of fear and joy she’s feeling, and hoped that Ferrell—and the other friends and family who received similar emails—would understand.
Harper Steele and Will Ferrell
At the beginning of Will & Harper, Ferrell explains his shock, but also his immediate desire to assure Steele that he supported her and loved her. He had questions, of course. So, too, did Steele: Will he think of me and our friendship differently? Will he act differently toward me? Will he be too afraid to ask the questions that would continue to build their friendship?
The bridge they ended up building to sort through all of that ended up spanning coast to coast. They decided to go on a 17-day road trip together, from New York to Los Angeles.
Steele has always loved being on the road, relishing stops in small towns off the beaten path, making friends with strangers over drinks in seedy dive bars. She liked going to car races and greasy-spoon diners, pulling over to have a beer while sitting in a lawn chair on the side of the road or in a Wal-Mart parking lot.
After transitioning, she worried that she wouldn’t be able to do those things anymore. She was concerned about her safety, of course, in areas of the country where anti-trans legislation is being passed and transphobic rhetoric and violence is an alarming concern. But even more at peace as herself than ever, there was discomfort; would her own insecurity about not being accepted in these places be the biggest hurdle to returning to them?
There was one sort of out-there solution to those concerns: What if one of the biggest movie stars in the world went on the journey with her?
Directed by Josh Greenbaum (who also directed the deliciously bonkers Kristen Wiig comedy Barb and Star Go to Vista Del Mar, for a sense of comedic sensibility), Will & Harper works on multiple pillars.
Ferrell and Steele have three decades of crackling, familiar chemistry when it comes to their senses of humor, and they have such an ingrained history that serious conversations about the transition and how they both feel about it unfolded with a surprising, very intimate honesty and vulnerability.
The film is a travelog illuminating where different parts of the country are when it comes to acceptance or having an empathetic curiosity about trans people.
Several of the signposts on that route are with people Steele has known and loved for years, starting in New York with having breakfast with her children—whose wisdom and emotional intelligence is astounding—and drinks at 30 Rock with SNL buddies Tina Fey, Seth Meyers, Paula Pell, Tim Meadows, and Colin Jost. As they travel across time zones, they stay with her sister, Eleanor, in Iowa, whose greatest sorrow after receiving Steele’s email was being clued into the pain that she was in for so long. They visit with Will Forte in New Mexico for a toast to a new beginning, and look back on what they learned about each other when they meet up with Molly Shannon in Los Angeles.
It’s heartwarming to see the embrace they’ve all given Steele. But what about the unfamiliar people? The ones who don’t know her. Who could clock her as trans. Who could bully her. Who could fling slurs at her, or worse.
In many places where one might think Steele would be ostracized, she’s accepted, in fact often with such grace that you might question your own prejudices. (Once you’re done crying at the beautiful scenes and exchanges.) In other places—when Ferrell and Steele sit in court seats at Indiana Pacers game, or when they have dinner at a raucous Texas steak house—the reception is so hateful they can feel it, and, soon, see it, when insults aimed at Steele and outrage that Ferrell would be seen with her flood social media and conservative websites.
Revealing that spectrum of experiences, though, is in some ways the point of the whole exercise. What was unexpected, at least for me, was how powerful the conversations between Ferrell and Steele would be.
Steele gave Ferrell permission to ask her anything he wanted to know about transitioning, with no concerns for propriety or offense. The result is that Will & Harper, because of those discussions, serves as a bit of Trans 101.
They talked about everything that it can sometimes, and rightfully, be considered inappropriate to discuss: how long Steele felt this way; whether she regretted not doing it sooner; her breast implants; considering bottom surgery; if it felt weird to encounter an old friend now a transitioned person; her voice; wanting to pass; sex and dating, suicidal thoughts and depression; feeling pretty—or sometimes not. Ferrell is never condescending, and often is moved to tears over his friend’s candor about how she’s felt over the years.
The film is never shy about the fact that Steele may be greeted with such friendliness at places because Ricky Bobby himself is alongside her and people are starstruck. It’s a privilege that she acknowledges, and it’s an opportunity—both for his friend and potential audiences—that Ferrell treats with pride and responsibility.
Will Ferrell and Harper Steele in Will & Harper
After the credits rolled, the audience stopped crying, and the second standing ovation dissipated, Steele told the crowd that it took a few months for her to agree to the idea of this road trip documentary.
“Bills were being passed all over the country,” Steele said. “It was looking—it still is looking quite awful. It’s ramping up. So I have this friend—this is my privilege—I have this friend whose movies appeal very broadly to a lot of people. That was the deciding factor. I can abuse this relationship for the good [of the trans community]. I still don’t know if Will knows what he did.”
After watching the film and hearing her speak about it Monday night, it’s obvious that Steele was joking. The movie doesn’t have distribution yet, but conversations after the screening skipped over how quickly it would get picked up to start guessing for how much. It’s incredibly entertaining, and emotional in a way that only a documentary made with such authentic, all-in intention could be.
Ferrell will get eyeballs on this movie, and, it must be said, has already faced backlash for doing so, even before it’s been released. That attention—brace yourself for round two of triteness—will be powerful, given the humanity and enlightenment the film boasts; yes, it could save lives.
Senior Editor, Obsessed
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