From left: Will Ferrell and Harper Steele in 'Will & Harper' Courtesy of Netflix Share on Facebook Share on X Share to Flipboard Send an Email Show additional share options Share on LinkedIn Share on Pinterest Share on Reddit Share on Tumblr Share on Whats App Print the Article Post a Comment "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. Related Stories TV These Are the (Other) "Horrible Things" Charlie Brooker Almost Included in the 'Black Mirror' Season 7 Opener TV 'Only Murders in the Building' Showrunner John Hoffman Teases Season 5: "We're Doing Something We Haven't Done Before" 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
The Hollywood Reporter
'Will & Harper' Director Jokes That Getting Pulled Over Didn't Require Using "The Will Ferrell Card Much"
August 14, 2025
4 months ago
3 celebrities mentioned