Isobel Grieve
Beautifully filmed and edited, Will and Harper (dir. Josh Greenbaum)Â is a remarkably warm documentary following old friends Will Ferrell and Harper Steele travelling across the United States from New York to California for the first time since Steele began transitioning in 2020.
Will and Steele met at Saturday Night Live in 1995 when they started working the same season, Will as a cast member and Harper, then known as Andrew, as a writer. The two became thick as thieves and created some of the most wacky and iconic characters SNL has ever seen.
The documentary premiered at the Sundance Festival this year to great applause and was quickly acquired by Netflix for its Fall/Winter slate. Its release is highly anticipated by comedy lovers, travel enthusiasts, and curious trans rights activists and allies.
I would highly recommend watching Will and Harper when it comes out. It’s more than an on-the-road documentary; it’s akin to Ewan McGregor’s series Long Way Down (2007) and Long Way Up (2020), although with slightly different themes.
The documentary teaches us more about Will and Harper’s friendship; we grow to understand the headspace of Harper Steele and the emotional process which led her to transition. Will and Harper have an interesting angle for documenting this road trip as pre-transition. Harper was a regular cross-country driver and lover of sketchy dives, and as a white man, was accepted, but as a newly transitioned woman, the trip came with a lot more fears and hesitation. As the two buddies travel, they are surprised by the wonderful acceptance of Harper’s gender in some spaces and how wildly ostracized she is in others.
At an Indiana Pacers game, Ferrell was forced into a crisis with a state governor who passed anti-trans legislation. Forced to play nice at the moment with no context for who he’s meeting, Will and Harper politely say hi. However, later, the two reflect how complicated and erratic that moment was and how quickly a photo with that governor turned hordes of online critics on their tail.
With the characters Ferrell has played mocking uncritical right-wing dupes, he’s still a bit of a legend to some of he crustier bigots around. That made it particularly hard to watch Will and Harper in a Texas steakhouse, where things turn quickly from ‘Yay! Ricky Bobby!’ to ‘Ew, Will Ferrell has a trans-friend, how depraved.’ It’s truly disheartening but it’s also not the end of the world for these two. They take it in stride and keep going.
As much as it was fun and heartwarming to see these old friends traipse across the country with almost no hiccups, it’s not hard to assume that with cameras present people are in a position to behave better. The presence of a celebrity makes people put on a nice show. In some of these spaces it may have been a much different reception for Harper if they weren’t making a documentary. What was mild might turn dangerous when alone. It’s hard to know if Harper would be safe to go on this road trip by herself.
Though I don’t think the purpose of Will and Harper is to speak to all trans people traveling across the country. Instead of being a huge PSA to trans people: ‘This is how you travel, this is your beacon of light through the rough,’ it’s more, ‘Harper, you can do this!’ There’s no claim that all trans people can and should take this trip, it’s the encouragement that Harper needed to make this trip.
And for Will, going on this road trip, showed that their friendship hadn’t changed. At the beginning of the doc, Will expressed concern that he didn’t know who Harper might be now, had the boundaries changed. And Harper felt that she was shedding, becoming her true self and didn’t know if they’d click the same. However, after a quick awkward meeting at an obscure golf course, Will and Harper’s chemistry sparked immediately. Their friendship strengthens and blooms through the film and we have the pleasure of being a fly on the wall in these beautiful moments of connection and vulnerability.
Will and Harper shows a different side of Will Ferrell that I was happy to see and it makes me want to go back and rewatch every collaboration between Will and Harper with an introspective eye.
