In “Will & Harper,” comedian Will Ferrell meets an old friend for the first time

About halfway through “Will & Harper,” the new road trip documentary from director Josh Greenbaum, comedian Will Ferrell looks across the car at his longtime friend and collaborator Harper Steele and says, already laughing, “Here's a question: Do you think that being a female driver makes you a worse driver?”

At this point, the couple has been on the road for over a week on the 16-day, cross-country tour that serves as the basis for the film. The film explores how coming out as transgender can change a friendship, set to a soundtrack of soulful, road-ready tunes. And Steele's mock-exasperated “Fuck you” in response shows how far the friends, who met on the set of NBC's “Saturday Night Live” in 1995, have come since that first day of the trip.

“Josh warned us that it would feel weird the first few days, but by the third day, you forget the cameras are there. And that's really true,” Ferrell told NBC News in an interview with Greenbaum and Steele about filming the documentary, which hits Netflix on Friday. “By that third day, you really get used to just hanging out, like you would if there were no cameras there, and I think that's true to what you see.”

While it takes a little longer for Ferrell to start making jokes about female drivers and Steele's “boobs,” by the time they get from New York to Indiana about three days later—where they watch the sunset in a Walmart parking lot with a comical assortment of Pringles—they're already headed in that direction. And what begins as a series of cautious conversations about the basics of gender transition eventually evolves into touching and often hilarious dialogues about mental health and authentic living as they head deeper into the Midwest and turn south in Steele's vintage station wagon, en route to California.

“There was really no question whether there would be humor. Would anyone else find us funny? We didn't know, but, boy, do we really make each other laugh. And we're lucky that the audience seems to think the same for the most part,” Ferrell said, before Steele joked that it was still unclear whether viewers laughed. with she or at them.

“That's our language – that's how we met – we joked around,” Ferrell said, explaining that while they knew making the documentary “wouldn't be an easy undertaking,” they weren't afraid of it because of their past. “The wonderful surprise is that we met through humor, but once we met, we had really great, emotional conversations about other topics.”

The road to “Will & Harper” began in 2021, when Steele wrote a letter to her close friends and family telling them she was undergoing gender reassignment surgery. Ferrell responded with a supportive message, adding that he would like to talk about it at some point. Of course, when he said that, neither of them had in mind talking about it on camera for a highly acclaimed documentary screening at a festival.

“It was Will's idea, but I turned it down pretty quickly,” Steele said of Ferrell's suggestion that they reconnect and film as they drove across the country. “And then I gave myself about a summer to think about it. I started talking to Will, and then we brought Josh in, and we all talked about what form it would take.”

A big part of why it took her so long and had to go through multiple interviews to agree, the former “SNL” head writer explains in the “Will & Harper” press notes, is that she prefers to stay behind the scenes. But the feeling that the documentary could help other trans people and push her to put herself in situations that made her feel uneasy after coming out ultimately outweighed her fear of being on camera. And once she was on board, she said, she jumped at the opportunity to be open about her transition in the film.

“I've never been too afraid to talk about myself,” she said. “When you come out as transgender, you show a kind of vulnerability that turns out to be very special, so I embraced it.”

After Steele agreed to the project, she and Ferrell mapped out an itinerary that included places she'd visited on her many previous road trips across the country before her gender reassignment, as well as sites from her past. And Greenbaum, whose other films include “Too Funny to Fail” and “Barb and Star Go to Vista Del Mar,” enlisted a crew to help him photograph the two taking in local sights — like a Pacers game in Indianapolis, a restaurant serving a 72-ounce steak in Texas and a hot-air balloon ride in New Mexico — or simply enjoying a beer and the view from Steele's handy folding chairs.

Between stops, the friends discuss topics like Steele's decision to use the name Harper, their experiences with breast surgery and gender dysphoria, and Ferrell's love of Dunkin' while being filmed by a camera mounted on the hood of Steele's car. And en route to places where Steele questions whether she's still welcome, like a rural dive bar or a stock car race, they talk about their shared feeling that large parts of the country have become unsafe for transgender people — something that was also a major theme for Greenbaum while making the film.

“On one hand, it was great that we all knew each other. But there was another level that I wasn't used to: I'm not just thinking about what's good for the story; I want to protect my friends and make sure they're literally and physically safe,” Greenbaum, who has known Ferrell and Steele for years, told NBC News about filming his first documentary with his friends as protagonists.

He added that he was careful to keep Steele and Ferrell “emotionally safe” when editing the film, saying, “But I just followed their lead because, as you see in the film, they're so open and vulnerable. I knew that was a safe place to start – to show exactly what happened on that journey, both the good and the bad.”