At a glance, the premise of Will & Harper is simple: two longtime friends set off on a cross-country road trip. But the upcoming Netflix documentary, which stars SNL alums Will Ferrell and Harper Steele, is also a charming, funny, and, at times, emotional, story of reconnection, explored along a 16-day journey across the United States.
Fueling the voyage is a change in Steele’s identity. The Emmy-winning SNL writer has been good friends with Ferrell since the two joined the late-night comedy show in 1995. Steele became head writer of the show in 2004, and wrote some of Ferrell’s sketches. After Steele left the show in 2008, the two continued working together on Ferrell’s production company Funny or Die and have collaborated on numerous projects. Among them Steele co-wrote Ferrell and Rachel McAdams' 2020 comedy, Eurovision Song Contest: The Story of Fire Saga. They attended Lakers games, barbecues and surprised each other at dive bars.
Steele came out as a trans woman in 2021 in an email sent to friends and family ("I'm old now," she wrote.) Some time after receiving this news, Ferrell pitched Steele the idea for a documentary. It would be filmed on a cross-country road trip, which, along with occasional hitchhiking escapades, Steele had been known to enjoy. He would accompany her, stopping at places beloved by the two of them and allowing Steele to visit them, for the first time, as her authentic self.
“He wanted to make sure that what he was about to say didn't sound exploitative. He wanted to do this road trip with me. But… I've known him for long enough. He's not an exploitative human being,” Steele said on IPR’s Talk of Iowa.
At first, they laughed about it. Steele summed up the proposal as “a funny thought” and initially turned it down, uncomfortable with the idea of being "on that side of the camera."
But a few months later, she began to see the idea as an opportunity. Not only could the trip offer a chance to become more comfortable with her newfound self and "come out even more," it could open up conversations across the country about transness, especially as anti-trans bills and laws were being passed, including in her home state.
And so the two set off. They start at SNL's home 30 Rockefeller in New York City and end at home in Los Angeles. In between, they cross the heartland. Iowans may recall their stop in Iowa City, where Steele grew up, in 2023. Steele recalled a crowd growing outside of Deadwood bar within minutes. It was a common occurrence she’d gotten used to around the Anchorman star over the course of their friendship, and it had only intensified in the age of smartphones and social media. But the presence of her friend, and his celebrity, was one of the reasons she’d agreed to do the documentary at all.
“When you're going across the country as a trans woman without a camera crew and without Will Ferrell, the experience is quite different,” she said. “It can be a little more fraught.”
But when you’re in the company of Ferrell? “Everyone wants to talk to you,” she said. Not just in New York and LA, but people in red states, too, like Iowa.
“I would like to feel very comfortable in my own home state, so I think that was part of the mission," she said.
Will & Harper will play in select theaters ahead of ahead of its release on Netflix on Sept. 27. It will be screened at FilmScene for two weeks starting Sept. 13. Steele and Ferrell have filmed a special video that will play before every screening.
To listen to this and other conversations with Iowans, listen to Talk of Iowa, hosted by Charity Nebbe. Samantha McIntosh produced this episode.
