“I-40 is my favorite highway in America,” says former Saturday Night Live head writer Harper Steele. “That said, going through Colorado on 74 is, without a doubt, one of the most beautiful scenic things you’re going to see.” Steele, as a longtime lover of roadside dive bars, truck stop diners and cross-country road trips, would know.

In the documentary Will & Harper, a 17-day road trip is the vehicle for Steele to reconnect with friend and longtime creative collaborator Will Ferrell after she came out as trans. The duo talk about Steele’s transition, her experiences as a trans woman and their friendship as they cross the country with stops at dirt racetrack derbies, a hostile Texas steakhouse and Steele’s native Iowa City, experiences that run the gamut from joyous to harrowing.

The doc, which The Hollywood Reporter called “a portrayal of deep, sustaining and supportive friendship,” received a standing ovation at Sundance, a feat in and of itself being that American festival audiences prefer to keep their seats as compared to their European counterparts. And, in the 18 months since, it has continued to earn awards recognition, including five Emmy nominations, among them outstanding documentary or nonfiction special.

At first, when Ferrell suggested the duo bring a camera crew along for a planned cross-country jaunt that would start in New York, Steele wasn’t sold but ultimately found two motivators. “There were a lot of laws and things being offered up to state houses all across the country. The anti-trans stuff was building and building and building,” remembers Steele. In the doc, Ferrell and Steele encounter Indiana Gov. Eric Holcomb, who later signed a gender-affirming care ban in his state. She saw Will & Harper as a chance to inject joy, positivity and greater understanding into the conversation surrounding the trans experience when headlines are often disheartening, at best. She continues, “Motive number two is Will and I have never done a documentary. It’s like, ‘Yeah, this is crazy, and that’s why we should do it.’ ”

Director Josh Greenbaum was primarily known for such narrative comedies as Barb & Star Go to Vista Del Mar and such series as New Girl, but his early work is primarily in nonfiction with features including The Short Game. While the documentary to studio comedy pipeline isn’t exactly a well-trodden path, it meant that Greenbaum, who had worked with Ferrell on the 2023 talking dog comedy Strays, was the ideal filmmaker for the project.

Greenbaum was happy to make the jump back into the genre, saying, “In docs, you’re going out and hunting for things every day, and you’re hoping to set up an environment where interesting things can happen and you’re prepared to capture it, but you may come back from the hunting expedition kind of empty for the day.”

The filmmaking team charted their course and set up.

“I don’t think this is legal, so don’t get me in trouble, but we suction-cupped and ratchet-strapped down two cameras on the hood of Harper’s Wagoneer,” says Greenbaum. The two-shot of a driver and passenger through a windshield, whether in narrative or nonfiction, is a personal favorite of Greenbaum’s: “The audience gets to choose who they want to look at when. Sometimes watching the listener is as interesting as watching the person speaking.”

A wood-paneled Wagoneer laden with high-end camera equipment is not a common sight on the road. It probably didn’t help that the car couldn’t top 55 mph without starting to shake uncontrollably. Greenbaum recalls with a laugh, “We did get pulled over once, and we didn’t have to use the Will Ferrell card much.”

The director was concerned about Ferrell and Steele being able to fill hours at a time on the road with a continuous stream of conversation. Ahead of filming, the director reached out to his subjects asking for questions they would like to ask each other, creating a lengthy document. Greenbaum was in a car driving ahead of the Wagoneer, with a live feed to the video so he could watch the duo’s conversations in real time, occasionally lobbing questions over a walkie-talkie or by text. Any fears about lengthy silences proved unfounded.

“They didn’t really stop talking,” says the director. This proved to be its own issue. Comedians don’t like silence, so Greenbaum says he gave the friends “the documentary filmmaker slash therapist lesson, which is: If you want to let somebody open up to you, ask a question and then stop talking. Just stay silent even in the awkward pauses. You’re giving them time to process their answer.”

For Steele, the trip was markedly different from the average — massive camera crew aside — in both practical and intangible ways. Normally, she would pull 16-hour days behind the wheel, not a possibility with a union crew. She also has a mood-dependent rotation of road trip music — soul, jazz, country, etc. — but playlists don’t make for great film audio. She enjoyed the company and the conversation that the setting allowed, saying, “I love a friend in a car with you, because there’s an ability to be intimate without having to look at someone. It makes it almost easier.”

By the time the crew reached Los Angeles, the trip’s end point, Greenbaum had 250 hours of footage to sift through. He first focused on the story’s emotional beats before layering back in Steele and Ferrell’s jokes and bits. He says, “You hear it from any filmmaker who works in comedy, which is to take the comedy out and ask: What’s the dramatic story happening here?”

The Sundance premiere was nerve-wracking for Steele, she remembers. “It’s not like I haven’t put something out in the world and waited for the audience to tell me it sucks or they love it,” she says. “But it was scary, because they’re going to be loving or hating you.”

She brought her three daughters to the screening at the Eccles, where they watched the movie with the thousand-plus audience, who remained largely quiet, taking in the film’s nearly two-hour runtime. “As a comedy writer, you hate silence,” she says. “But there was so much silence in this thing that my head is going, ‘They’ve dropped out. They’re not paying attention anymore.’ “

When the movie ended, the crowd immediately burst into applause. Steele was in disbelief but remembered a note that Greenbaum gave her during filming that told her to “let the love in.” In the months since, Steele has welcomed the people who have approached her on the street to talk about the doc in the same way: “You’ve got to let the love in.”

Greenbaum surmises, “You hope to impact people or to move people at an individual level, and maybe, if we’re really optimistic, shifting culture in some little way.”

This story first appeared in an August stand-alone issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.