About three years ago, Will Ferrell’s longtime friend Harper Steele—a writer-producer who worked with the comedian on Saturday Night Live, Eurovision Song Contest, and more—came out as a transgender woman. And Ferrell responded exactly like a big-hearted, beer-crushing Will Ferrell character: Let’s take a cross-country road trip to talk about it and make a documentary of the whole thing!
The duo worked with filmmaker Josh Greenbaum (Becoming Bond, The Short Game) to capture the entire journey, which would also function as Steele’s first time truly living in the world as herself. The trek includes but certainly isn’t limited to: uncomfortable, teary-eyed conversations in a car, a steak dinner gone wrong and one blissful karaoke night. The result is the hilarious, beautiful, and deeply important Will & Harper, which debuts on Netflix.
Now, it would’ve been enough to show Steele and Ferrell’s sprawling, My Dinner with Andre–style talks on the ride. But that’s not what makes Will & Harper one of the year’s best—if not the best—documentaries. Greenbaum delivered a striking portrait of coming out as transgender in a year that, as of June, saw US legislators consider 617 anti-transgender bills (and a potential president in Donald Trump—who, if he wins, poses a major threat to transgender Americans). We watch as Steele finds support at a rural bar but face staggering hate at a seemingly benign Texas steakhouse. “If you start to engage and listen to people like Harper and so many others, you’ll realise, These are just people who are trying to live their lives,” Greenbaum says.
Below, he opens up about following Ferrell and Steele across the United States, the potential political impact of the film and his next directorial projects, one of which just so happens to be Spaceballs 2. This conversation has been edited and condensed for clarity.
ESQUIRE: Has anyone asked how the road trip was for you? I mean, you also traveled the country.
JOSH GREENBAUM: You’re right! No one actually has asked me that. It was a mix of things. Of course, I’m just so focused on figuring out how to capture the footage.... On the flip side, I was going on this journey with them. Both of them were friends of mine prior to making the film, so they’re certainly the subjects of my film—but there was another added layer of going through all the emotional ups and downs that they were going through. In any given scene, I was in the background—usually in my car—and I could be laughing. Then at some of the heavier moments when they both broke down, I was crying.
You were feeling the emotional and physical toll of a road trip.
I knew there would be some highs and lows but where they came completely surprised me. I’m just thinking of when we have a silly dinner where Will’s going to try to eat a 72-ounce steak [and it was a low]. Then there were times when we went into a bar that I thought was for sure going to be a low. I thought, Oh, I scouted this bar that Harper said she wanted to go in by herself—and I am certain this is not going to go well. Every time I had a preconceived notion—which is certainly a lesson for me and for anyone involved—it [might not always play] out the way you might expect.
There’s a statistic: 70 per cent of people don’t directly know a trans person.... The unknown with Harper became known as soon as she walked into places. She’s so personable and funny that all of a sudden that scary unknown became Oh, okay, she’s cool. She’s funny. She likes shitty beer. And you go, This thing that I was either apprehensive about or afraid of, it’s not so scary all of a sudden. Obviously, it’s a huge burden to put on one person.
Was there a point when you realised that Will and Harper’s conversations could act as a point of entry—and empathy—for people who don’t know much about transgender issues?
That was the intention from the start.... By seeing someone like Will with his friend Harper—and the two of them not so perfectly make their way through these understandably difficult conversations—it does create an easier on-ramp and lowers the bar of entry for people to feel like they can engage. One of the lessons I took was: A lot of us want to engage, be allies, and be there for a friend. But there’s a fear of saying the wrong thing, not knowing what to say, doing the wrong thing, or asking the wrong question. What Will and Harper showed throughout this journey is that a lot of being an ally and a friend is just being there. Listening. You don’t always have to say the perfect thing, provide the best advice, or ask the best question. Just show up.
I feel like a lot of people who watch this documentary will meet Will Ferrell—who is far more even-keeled than his onscreen persona—for the first time.
One of my favourite moments was when I screened Will & Harper for some close friends and family. I screened it for Will’s dad and he was in tears at the end. He hugged me and said, “That’s my boy up onscreen. That’s the man that I raised and know and love.” He said it’s the thing he’s most proud of that Will’s ever done.... Will is an amazing guy and I’m really excited for the world to see the side that I’ve known for seven or eight years now.
Having known Harper for several years, what did you notice in her over the course of the journey?
She has never wanted to be on camera. I dug through archival photos and footage of Saturday Night Live, where she started the same exact day as Will Ferrell. She was there for 13 years. I couldn’t find anything. She’s like, “I would hide. I would dive out of the way.”... Harper grows more and more comfortable throughout the film. By the end, there’s a giant sense of relief and joy. That was just an important part I wanted to convey, which was for so many trans people and queer people, when they come out, the actual feeling is joy. You see that throughout Harper’s journey as she just leans more and more into her joy.
It’s beautiful. You really can see the weight shedding off her back.
Now you should see her. She’s coming out to standing ovations at festivals. I was like, “Harper, keep an eye out. I want your head to get too big!”
I know people keep asking about the steak scene, where Ferrell and Steele are received poorly by the patrons of a Texas steakhouse. But what’s the opposite of that?
There was something about the karaoke scene [that was special]. Harper meets another trans person who has gone through it before. You can see that she’s learning, asking questions, finding a friend and they just bonded.... Will sang—in of course, classic Will Ferrell fashion—“She’s a Lady,” which is very fun and funny. And finally, the three of them settled on a song to sing together, Sonny and Cher’s “I Got You Babe,” which is just euphoric and beautiful.
Will & Harper premieres during an election season. Did you ever see the film as having any sort of political role?
I hope it makes a cultural impact. Everyone on the team consciously did not make what I would call a political film. It’s an incredibly personal film. But that’s where our politics should lie—in the personal. We can talk about all these hypotheticals and you can hear politicians spewing lies about this and that, about kids going to school and then two days later coming home a different gender. Utter bullshit. But the way to combat that is through storytelling—personal stories, levity, comedy and joy. Some people just don’t know a lot yet. What they’re doing is they’re listening to the wrong people. They’re listening to politicians.
We went through this, by the way, with gay marriages. A lot of the same arguments were being made. There was a lot of Oh, what if we let gay people get married? What will they do next?!?... There’s this subtle line that Harper says that I always go back to. It’s when she’s outside her house toward the end of the film, where she’s explaining that she’s just feeling such relief that she doesn’t have to lie and hide anymore. She says that she just wants to be in the world. That’s all she wants to do. She just wants to live.
On a lighter note—and this is a true story—I watched Spaceballs as a kid, but I didn’t see Star Wars until I was in college.
You’re like, “This is a lot like Spaceballs! George Lucas copied Mel Brooks.”
That’s exactly it. I can’t let you go without asking about Spaceballs 2.
Well, there’s not much I can share, other than I’m excited to make it. It’s a still a little ways out. Like you, I was obsessed with the movie. I’m older than you so I had VHS. Back in the day, we didn’t have Netflix. You just went to your seven VHS tapes that you had in your house—and that was one that was on repeat. So I started speaking with Josh Gad and then, of course, Mel Brooks to work on this. I’ve been working with him. He’s 98 and he’s still the funniest and sharpest person. It’s a total joy. I’m still in the doc world. I’ve got another documentary coming out that I can’t really speak to yet, but it’s the distant cousin of Too Funny to Fail, which was a doc about The Dana Carvey Show. That’s coming out earlier next year, before Spaceballs.
There have obviously been so many Stars Wars films and shows since Spaceballs. What’s new to satirise in the current state of Star Wars?
I think you could answer that, right? It’s fairly easy. There’s been a ton of Star Wars content. It’s just exploded beyond the fact that there have been not three but six Star Wars films made—and that’s just in the Star Wars universe. So there’s a lot of new [material to satirise], but we also certainly focus on continuing the old so it is a true sequel.
What hasn’t anyone asked you about Will & Harper yet?
I’m really proud of the music in the film. What’s a road trip without great music? This is the first film I’ve ever worked on that every song was cleared [by their respective artists to appear in the film]. I was told by so many people, “Don’t even try for Bon Iver’s ‘Holocene,’ because [Justin Vernon] never gives it.” I sent a note to Justin Vernon and he watched the scene—and loved the movie—and he granted us permission. Of course, it all comes to an end with the wonderful Kristen Wiig. She wrote a beautiful song to end the whole film.
Is the Academy Award for Best Original Song limited to narrative films?
No, it is not. We’re doing it. Let’s get Kristen Wiig an Oscar.
