How ‘Will & Harper’ Took on a ‘Whole New Meaning’ After Trump’s Election

A very funny road trip movie that also happens to be very moving, “Will & Harper” gets in a car with Will Ferrell and one of his closest friends, writer Harper Steele, for a trip across the United States in the wake of Steele’s gender transition. As Kristen Wiig’s theme song puts it: “Harper and Will go west/Just two old friends and two brand new breasts.”

How did you get involved in the film? It came after Will and Harper had already decided to make a trip across the country, and potentially film it?
Yeah. once the idea of doing this road trip came about, the possibility of it being a documentary is when I became part of the conversation, as a documentary filmmaker but also as a fairly long friend of both Will and Harper. I’ve known Will for about eight years, and knew Harper for about four. Kristen Wiig introduced us when she had Harper come in to do a punch-up on “Barb and Star Go to Vista Del Mar,” which was my first narrative film. They approached me and said, “Josh, do you think there’s a documentary here?” to which I answered, “Absolutely.” A few months later, we were on the road driving across the country.

Had Harper already come to terms with the idea of putting a very sensitive part of her life on film?
I think they had mostly gotten past that. I know it took a while for Harper to come around to the idea of not only of doing the trip but of it having it filmed. But I think that’s a reason why I made a lot of sense as director. I had a pre-existing relationship with both of them, which helped because it was super important for creating a very safe space for them to be able to be open and vulnerable and honest — not just for one another, which is hard for anybody, but in front of cameras.

And I think the three of us share a similar comedic sensibility. We all wanted whatever came out of it to be funny. I think Will and Harper’s love language is comedy, and so it was very important to them that whoever was directing this film had a sense of comedy. I think I was perhaps the last piece of the puzzle that made Harper finally just say, “Yeah, let’s do it.”

When you sat down to think about what this film would be, what were the big questions you had to answer? 
There were a lot. I think my first question was, What is the film exploring?  The concept of the trip was: Harper loves this country, but she’s not sure if it loves her back since her transition. She was going to the places she used to love, these small towns and dive bars, and seeing if she can still feel comfortable. So we had to make sure we had a small and nimble crew so that if Will and Harper had any idea of, “Ooh, let’s pop into this place, let’s go go-kart racing,” I was able to follow them with a crew.

The big second question was about their friendship and their relationship. It was a big change obviously for Harper, but as Will says in the film, it was uncharted waters for him. That was always going to be the deeper thing the film explored, and the more universal themes of empathy and love and acceptance and growth and change within a relationship.

But how do I capture that? A lot is going to be in the car. We came up with some fun creative ideas like mounting two cameras on the hood of Harper’s Grand Wagoner. One was a two-shot and it was strapped down. I also put a second camera next to it with a longer lens, and I had a remote head to pan back and forth.

And the last part of it was that I wanted to make sure I was capturing Harper’s version of America that she loves. She loves to find the beauty in the mundane and the quote-unquote ugly. So that goes down to choosing lenses, and I chose these beautiful old Cooke prime lenses that have soft characteristics to capture the way she sees America. 

Obviously it’s ideal for you if the conversations start out tentative and get more intense and open by the time they get three quarters of the way across the country. But can you tell them, “Don’t get into it too much in the first week?” 
It’s a very astute observation. That’s the concern — and by the way, not only that, but given the nature of how I was shooting it, where we’re tracking their trip and they start in New York and make their way across the country, you can’t really do what you can normally do in a documentary, which is take a scene that maybe happened 15 days in and edit it so it looks like it’s Day 2. That wasn’t on the table, given that you could see where we were in the country.

I had them both send me questions they wanted to ask one another, so I had what I called the question or conversation bible in case they ran out of things to talk about, which they shockingly didn’t across 16 days. But what really happened is the organics of how these conversations go. Nobody jumps into the most difficult conversation on Day 1, you know? It played out in the way that you expect, which is that they started in lighter, more comfortable territory, and as the journey went along they let some of their inhibitions down, both with each other and in front of the camera. 

What was it like sitting down with 250 hours of footage?
The word I would use is overwhelming, and I mean that in both a positive and negative connotation. The first cut of the film that I thought was really working was five hours long. And the secret was to let go of some of the comedy. They’re two of the funniest people I know, by far. But once I let go of that and focused on structuring the film around moments of growth and change and more emotional story beats, I got the film to a reasonable length and could start to fold back in the more comedic moments. 

In the film, the experience of traveling across the country did seem to help Harper figure out her relationship with this country and her view of herself. But the way the film has been received and embraced must have been a continuation of that journey in some ways.
Absolutely. All of us, but particularly Harper, have undergone incredible growth since starting to make the film. And then obviously this transformation has taken on a whole new identity since the film’s been released. Even making the film, one of my favorite moments was when she decided to go in alone to that bar in Oklahoma. She did not want Will by her side. She wanted to see if she could do this on her own. And she was met with a surprising amount of love and acceptance, even without Will in there, in a bar where I was certain that love and acceptance was not going to be the outcome.

And shortly thereafter she was at the race track and she said, “I think I’m realizing I’m, I’m not afraid of other people hating me. I’m afraid that I of hating myself.” She’s still on that journey — and I think a lot of trans people can relate to this, but also everyone can relate to this. There’s a universality in learning how to love yourself, all flaws and all. That’s what a lot of the journey of the back half of the film is about, and it’s been wonderful to see that continue as the film has been out in the world. 

Did the experience make you think that America does still love Harper?
Yes, but obviously we have a ways to go. The reality right now is that we’ve got a soon-to-be president who spent over $215 million on campaign ads that target trans people. I can speak for all three of us when I say our film took on a whole new meaning [after the election]. He and his loudest supporters regularly go after the trans community and spread division and hate in general, not just at the trans community.

The last time Trump was president, hate crimes spiked 20%. And for me and I think all of us, the only way to push back against this hate and division is with love and empathy. On social media, people have become nothing more than avatars and usernames. We’ve lost touch with each other’s humanity, and I feel a lot of politicians are exploiting that. And so stories like ours, stories of love and friendship and allyship, are how we fight back.

A version of this story first appeared in the SAG Preview/Documentaries/International issue of TheWrap’s awards magazine. Read more from the issue here.

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