Miranda Tsang: How did you go about planning this road trip? 

Josh Greenbaum: Harper was leading the charge because she’s done this trip hundreds of times. We mapped out a general route prior to departing: We knew we wanted to hit a few places, that they wanted to go to New York City to start the trip because they met at Saturday Night Live and Harper wanted to meet up with her children. We knew we were going to head over toward Iowa City where Harper’s from, and because it was wintertime, they wanted to head south. But what was really important to me was that I had a small and nimble enough team that on any given day, if Will and Harper got inspired to go somewhere and check something out, we were able to do it. So a big part of the planning was not just talking about where we may go, but keeping the crew really small and communicating, “Hey, this is documentary filmmaking. It’s fly by the seat of your pants. We all have to be okay with a change of plans.” The exciting thing about making a documentary is when you don’t know what’s next. We felt very lucky to have a lot of moments that happened organically; sometimes you are able to capture lightning in a bottle.

What hurdles came up directing a road trip film?

JG: There’s weather; we drove through rainstorms, hailstorms, snowstorms, and some extreme heat when we got down to the south. We would go into places trying to consciously be aware of the impact of our cameras, and [also] the impact that Will Ferrell has on the scenes. Something we talked a lot about early on was acknowledging that this is not the average trans person’s experience because of those two factors. So when we could mitigate them, we tried. We never notified places that we were with Will Ferrell beforehand because of crowd control but also to get organic interactions. And, when we could, we also tried to keep the cameras back and be on long lenses when we went into real spaces. We did no lighting, just really tried to strip things down.

You see, later in the film, there are a couple of moments where we also try to remove the Will Ferrell celebrity of it all from the equation, and Harper just decides to go into places on her own because she wanted to be able to do that in the future. Then, to maybe less success, Will had the idea to disguise himself. To be honest, I don’t know that anyone noticed it was him, but I don’t think he drew less attention based on the [ostentatious] outfit he put together.

Those moments were incredible. You had over 200 hours of footage; how did you decide what to include?

JG: It was a very difficult decision. I think the first cut of the movie was about five and a half hours. It was definitely an emotional journey for me — both the trip and then the [editing] process — but every day in the editing room I found myself bouncing between dying of laughter at their bits and then suddenly crying as we delved deeper into Harper’s story and the pain she endured. Then, all of a sudden
I would feel sort of reborn through their connection — the grace they showed each other and their genuine love for each other. So I tried to use that as the driving principle. 

The first step I took with my editor, Monique Zavistovski, was to identify the moments of their story that were dramatically important, moments of discovery between Will and Harper, so that I was really anchoring the film and making sure we were tracking the emotional story first and foremost. Knowing that Will and Harper are the brilliant comedians that they are, I also knew not to stay in that space too long as they tend to undercut serious moments with humor. I tried my best to emulate the patterns of their conversations, which, if you break them down, usually start with a joke, then transition into a real question in genuine conversation, and then return to comedy when things get too serious. And I love that about them, as it reflects how I see life as well.

Life is never just funny or just dramatic in any given moment. It constantly bounces between the two. And my favorite films and stories are those that can simultaneously be heart-wrenching and hilarious, somehow, at the same time. That was a big part of the process of how to whittle it down. I know that, in talking further with Will and Harper about why they thought I was the right person for this, they love my comedic sensibilities. We all share comedic language, and I’m a huge believer in the expression that laughter is the shortest distance between two people. So that was a guiding principle as well — I never wanted to lose sight of the fact that Will and Harper’s love language with each other is rooted in comedy and laughter, in terms of the film’s tone and its ability to connect with people.

Did anything surprise you about the people that Harper and Will met
on their journey or the interactions they had?

JG: In a way, every day was a surprise. In general, I think we all anticipated interacting with more antagonistic voices. What we found is truth in the adage, “It’s hard to hate up close.” When you watch the film, you can’t help but wonder, Well, Will Ferrell’s there, and there are cameras. But there are also many moments when Harper had interactions where cameras were far away and Will Ferrell was nowhere.

And I found that the overall sort of love shown to Harper — in the best-case scenarios — or just acceptance at a base level was really surprising and encouraging. That said, while we were on the road, we couldn’t help but pay attention to social media because people were tweeting and talking about it. That’s where you found a lot of hatred that was really hard to swallow. But I think Harper and Will were very brave in that they didn’t ignore it. I didn’t want to ignore it, in the sense that I didn’t want to not include it in the film. On one level, I don’t want to give voice to these people. But it would be disingenuous not to include that because it is part of the trans experience. My sincere hope is that those people who decided to write some of those words of hatred have a moment of reflection of, Why did I feel the need to write this incredibly hateful thing about a person who, now that I’ve watched this film, I can share a lot of humanity and similarity with?

Eventually, just by spending a lot of time together, Will and Harper begin to understand each other better. 

JG: There’s a softness and a grace that they afford one another. Just a little bit more grace keeps the conversation going, and through that, I think progress is made. And that gentleness carried through how I thought about the film as a whole. Even the way we shot it — we used old lenses that have a softer feel to them. I chose to use a Steadicam for all of our vérité work, which has a gentle kind of floating to it. Their relationship inspired me in all sorts of creative ways as to how to make the film. I had an amazing director of photography, Zoë White, who gave the film an elegant look and captured Harper’s perspective on America. America itself is a character in our story, and I wanted someone who could capture it through the lens of how Harper sees it, which is not going to the one beautiful vista that everyone goes to, but looking at the rundown steel mill or the small-town Main Street and finding the beauty there.

Can you tell me about Kristen Wiig’s theme song, which plays over the credits? “Harper and Will Go West” is so tender and funny. 

JG: Will and Harper had this idea that they needed a theme song for the road trip. They called Kristen, and [I don’t know if] they ever really believed she was going to make a song, but when you task Kristen Wiig with doing something creative and fun, she runs with it. Ultimately, while I was editing the film, she and I got together with music producer Sean Douglas, who helped us record it. I think she did such a great job of striking the right tone of what our film is and what their friendship is. It’s a beautiful message: A friend is a friend until the end. I couldn’t have asked for a better gift to wrap up our film on. It’s funny and sweet and all things Kristen Wiig.

Why is it an important time for people to watch this film?

JG: According to GLAAD, who was a big partner in making this film, as of 2023, only 28% of non-L.G.B.T.Q. Americans say they personally know a transgender person. What you realize is that most of what people know about trans people comes from the media. So the potential for stories like this to make an impact is immense and it’s not something that I take for granted. But as Harper will tell you, our film is just one story among many and we need more. Laverne Cox was in this Netflix documentary that I love called Disclosure, and she said that seeing trans people loved, uplifted, and well-regarded in film and TV can inspire others to step in when they see a trans person being harassed in the street and make sure the trans people in their lives are supported in ways that affirm their humanity. My hope is that this film can help do that. 

I see Will and Harper as a conversation. So, for those grappling with the issue on any side, it starts with not just talking but listening. Will begins the journey in the film with a lot of questions, but by the end, he becomes more interested in listening and being present, holding space for Harper, whether she wants to share or not. The lasting image of this film, for me, is of Will and Harper sitting side by side, whether it’s in the front seat of her car or in those folding lawn chairs that they brought everywhere, talking through Harper’s transition and its impact on their friendship. That encapsulates the whole point of the film for me, which is for anyone with a friend or a loved one going through a significant change or a challenge, the message is to show up. That’s what being an ally is at the most personal level, and that’s obviously what being a friend is. I think a lot of people want to be an ally, they want to help, but they don’t know exactly what to say, what the right question is. I hope that this film serves as kind of a guide that it’s not as complicated as you might make it. It boils down to being there, showing up, and holding space for that person in your life.