Will Ferrell, His Trans BFF, and the Road Trip to the Oscars

People have been having to check in on Will Ferrell’s ego. It might be taking a hit. Josh Greenbaum, who directed the Netflix documentary Will & Harper, is concerned.

Greenbaum followed Ferrell and his good friend Harper Steele as they drove across the country. The road trip was meant to reconnect the pair, who met when they joined the Saturday Night Live staff at the same time, after Steele came out as transgender in 2022. As they worked through all of Ferrell’s questions about Steele’s experience, hopes, and fears, Steele reacquainted and realigned herself with a country whose highways she’s traversed so many times, but now for the first time as Harper.

Many things happen over the course of that road trip and the ensuing documentary: Ferrell and Steele forge a gorgeous new emotional bond and understanding of each other; the audience receives an intimate education of the anxieties, joys, and everything in between a trans person experiences; Steele discovers a way to move through the world, its prejudices, and its capacity for acceptance as Harper. And superfluous to all that—yet, perhaps, above all that—Steele becomes an irresistible star.

“The biggest joy I have is when Harper comes out Q&A’s,” Greenbaum tells me, speaking at the SCAD Savannah Film Festival, where the film had just screened. There is, reliably, a standing ovation. He will come out on stage. Ferrell will follow. “Then she comes out, and the cheers are always double the volume.”

“I’m hoping Ferrell’s ego is still healthy enough,” he says, laughing. “We’ve been jokingly comparing their Star Meters on IMDb. We have a text chain where we’re like, ‘Oh, Harper’s is higher than Will’s…’”

Like so much of Will & Harper, the good-natured laughing underscores its impact.

Following its debut at the 2024 Sundance Film Festival, where I first saw its ovation shake the rafters of a theater littered with tear-soaked Kleenex, the movie has been a fixture of the fall festivals and, now, the awards circuit. It was released on Netflix on Sept. 27, and has since won the Critics Choice Award for Best Documentary Feature (tying with Super/Man: The Christopher Reeve Story), and is tipped for an Oscar nomination in the same category.

Greenbaum’s been on the road again, this time for the better part of a year, showing Will & Harper around the world and meeting audience members after. He’s been thinking a lot lately of a quote from legendary critic Robert Ebert: “For me, the movies are like a machine that generates empathy.”

“That’s what I’ve been witnessing with this film,” he says. He tells me about being approached by a man after a recent screening who began talking to him about his trans daughter and how they struggled with their relationship as she transitioned. “Then he goes, ‘Speak of the devil!’ And she comes up running up,” he says. “They got to see the film together, and they bonded over it.”

With Will & Harper speeding down the highway towards the Academy Awards, we chatted with Greenbaum about the surprise of seeing two comedians be so earnest, the power of Will Ferrell lending his to supporting the trans community and risking backlash, and getting Kristen Wiig to write a joke song that ended up being so good it might just win its own Oscar.

You embark on this road trip with these two friends who are such big personalities, with intentions that are very intimate. What did you imagine it would be like, and how much did the actual experience differ from those expectations?

You go into any documentary with some degree of expectation of where you think the story is going to go. And then the joy of making docs is that it never goes where you thought. My expectations going in were a few things. I knew one of the questions the film was asking was: Harper loves this country. Will it love her back? In a lot of ways, I was pleasantly surprised by how she was received in certain circumstances, as you see in the film. And other times, certainly online, less so…

Which tends to be the case, unfortunately.

We did kind of discover that adage, that is it’s hard to hate up close.

I had the experience where I saw my own prejudices thrown back at me while watching the movie. Places where I assumed that people would treat her poorly, they actually embraced her really gracefully.

Really gracefully. And in manners of that. On one end is showing love, which she received a lot of on the trip. But on the other end of acceptance was apathy. Which I think we both love as well, right? Somebody who does not care. ”I don’t care. Go have your drink. Great to meet you. I’m here with my friends at the bar. It’s not a huge deal.” When the day comes that people watch this film and go, “What’s the story there?,” then we’ll know we’ve done it right.

Wouldn’t that be something?

That was one of the expectations going on. The other one was, on a deeper level, it’s a film about friendship. It’s a film about enduring friendship, long lasting friendship, and how we grow and let each other grow and change over time. I think you get a sense early on in the film that Will and Harper are going to be OK, but you don’t know to what extent. You don’t know what their relationship is going to look like on the backside of this trip and this very, very long, extended conversation, where they’re working their way through that.

Did you have an idea of how open they would be? It was really striking to me that Harper was willing to answer every question, and also Will was actually willing to ask every question.

That was my other expectation, or fear. They’re comedians. And for anyone who works with comedians, they’re not always the most open books about their own lives. They’re not the most vulnerable. They’ve learned maybe to use comedy as a force field, a protective layer to never let you really inside.

They certainly did open up.

They did, and I was surprised every day. I think Harper was there early on. I think part of what she’ll tell you is the act of transitioning and coming out publicly just led to more and more acts of bravery and courage. I think she led the charge in many ways, and Will started to follow. And I think to your point, he is very brave in asking questions, maybe in the wrong way, and not always phrasing things perfectly. He sort of stumbled through these conversations warts and all. And I think that’s important. It showed me that to be an ally isn’t as complicated as we might make it out to be. It’s to show up and listen.

I also think there’s something powerful about it being Will Ferrell who’s doing this. He’s a person that people think of as like their dad, or the Everyman—that kind of type. So for him to be this vessel for curiosity and acceptance, I think that’s really interesting.

Yeah, he is. And to be totally transparent we all knew that going in. I don’t want to speak for her solely, but I know, having done lots of Q&A’s and panels with her now, a big part of Harper’s reasoning for agreeing to do this trip, which she was hesitant to do at first, was seeing the unbelievable amount of anti-trans bills that were passed last year. It’s just like, oh, maybe this, and using Will’s celebrity to some extent, can help change culture. He’s a really easy on ramp for a lot of people who maybe wouldn’t engage in this story prior. Will is, I’ll call him the gateway drug to our story.

That’s exactly how I’ve been describing it to people.

It’s like, “I like Will, maybe I’ll check out what he’s doing next.” And you didn’t think you were going to watch this documentary about him and his friend who’s transitioned, but now you’re paying attention because it’s Will Ferrell and you loved him in Elf. I think Will himself was very aware of that. If only more celebrities would use their celebrity in ways like this, champion causes that need them in a very personal way.

That’s how it should be.

As you see in the film, Will’s a pretty private person. If you watch him and he goes on talk shows, he’s usually in character. He doesn’t share a lot about his own personal life. In this film, as you see, he really opens up, um, and you get a really good sense of who he is. My favorite moment of showing this film was when I finally showed it to Will’s dad, who came up to me in tears saying, “That’s my boy on screen. Thank you.” It’s his favorite thing that his son Will’s ever done.

And there’s a portion of the fan base that might not like that he did this. It was actually a risk.

He knew that risk and was absolutely willing to take that on. I think he would tell you,if there’s any backlash from his fans, he would say, “Good riddance.” But to be honest, we’re now at the backside of it and, I can’t speak solely for him, but there’s been just an overwhelming amount of love and support from all walks of life and from people.Certainly in my own life, to be frank, people who I would have thought would have not responded well and have grappled with a trans issue, if we want to call it that—I don’t love calling it that—they’ve come out and saying, wow, thank you for this. Seventy percent of people apparently don’t directly know a trans person or think they know a trans person.

That’s an important statistic.

It’s this unknown, and we unfortunately as human beings fear the unknown. When you watch the film, well, now you know Harper, and she’s fantastic. She’s funny, and she’s charming, and she’s acerbic, and she’s complicated, and friends with Will Ferrell, and all these things. You go, “OK, now I know her. What was I, what was I so afraid of, or misunderstanding?”

It has to be really fun for you to see Kristen Wiig’s original song be a huge part of the Oscar conversation already this year. How amazing would it be if that happened?

It’s funny. Years ago, the last time I worked with her was when I made a movie called Barb and Star Go to Vista Del Mar.

Which, I bow down to you forever for that movie. It’s perfect.

Oh, thank you. It was really fun. Will Ferrell produced it, by the way. So that’s when I first met Will. And actually I met Harper prior to all of this, too, because she came in and gave punch-up jokes on Barb and Star. We did All things go back to Kristen Wiig. So that’s why, so I gravitate towards Harper because of Barb and Star.

That’s just amazing.

Exactly. The song started as a joke of like, let’s call Kristen and task her with making a theme song for a road trip. ANd it became real. Kristen was like, “Alright!” She called me, she was like, “Dude, am I really making this?” I was like, “I’d love it. I would use it in the film if you make it.” I helped her a little, and then I brought in a friend named Sean Douglas, who’s a great songwriter, and he helped record it on her ukulele.

The song is legitimately good, not just a joke.

It’s a joy. It’s a beautiful song. After making the whole film and editing it, the last thing I shot was I drove to Kristen’s house, and got my iPhone out and shot her in her backyard singing it. And at one point she’s like, “We should put a hairdryer on me. So my hair is blowing while I’m playing the sax.” And I was like, wait, do you have a leaf blower? And she’s like, yeah. So I’m in the backyard shooting Kristen with a leaf blower as she’s playing sax. Her husband came home during that, and he just shook his head and kept walking like “another day in the life of Kristen Wiig.” But yeah, if she could get an Oscar, that would be, that would be amazing.

Speaking of the end of the film, the scene at the beach at the end of the road trip where Will gives Harper that beautiful pair of earrings just about broke me. It was so lovely.

It’s funny because I actually know where it came from. It’s not included in the film, but when the two of them went to the Indiana Pacers game, what didn’t make it into the film was after the game. The Pacers’ coach invited Will and Harper to the backstage of the locker room. They met everybody. They met the coaches. The first female NBA coach is on the Pacers, and Harper was talking to her. She had these beautiful diamond earrings. She said to Hareper, “If I could help with anything…” and Harper made a joke saying, “Well, I’ll take your earrings.” Will clocked that. That’s where the idea came from. So it was two weeks later that he figured out how to get these beautiful diamond earrings for her.

That is beyond sweet.

It’s a beautiful moment of a friend showing up. I love what he says in that moment, that the earrings are a symbol of our friendship and of this trip, but also a reminder of yourself to just let yourself be beautiful and love yourself. When I was editing the film, I realized the first half of the film is very much a look at this question of Harper loves America, will it love her back? But there’s that moment after the Oklahoma bar scene at the dirt racetrack where everyone’s actually really loving to her.

That’s one of the moments that took me by surprise

Harper says this line, where she realizes “I’m not afraid of these people hating me. I’m afraid of hating myself.” She was crying and Will was crying and I was behind the camera crying. But the back half of the film really becomes that it’s a journey of whether or not Harper can learn to love herself. There’s a universality to that. I think we all struggle with that. So that final moment of Will giving her those earrings is another way of saying, “You deserve to love yourself. You’re a beautiful person. Let yourself be beautiful. Let yourself see your beauty.”