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Will Ferrell and Harper Steele on Their Hopes and Fears for Their Doc Will & Harper

The powerful Netflix film explores trans identity and rights across the country, and Ferrell knows some of his fans may not react well. “I accept the challenge,” he says.
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In Netflix’s upcoming documentary Will & Harper, Will Ferrell and his friend of nearly 30 years, former Saturday Night Live writer Harper Steele, go on a road trip across America. The premise might sound silly: Do we really need to see one of the country’s most famous comic stars wander into an Oklahoma bar or a Texas rest stop, and banter with his fans? This turns out to be the furthest thing from director Josh Greenbaum’s mind. Will & Harper intimately examines a friendship during a period of nuanced, awkward redefinition, spotlighting that against a complex social backdrop.

The documentary (streaming beginning September 27) begins with Steele informing Ferrell of her gender transition. While Ferrell immediately expresses unconditional support for his friend, with whom he recently cowrote the film Eurovision Song Contest: The Story of Fire Saga, reality quickly settles in that things will change. The road trip idea materializes from a few angles: Steele loves traveling the country, but understandably fears doing it as an out trans woman, given the bigotry and discriminatory laws in different pockets of the US. And what’s in it for Ferrell? With this much time together, his old friend can educate him on what it means to be trans, why she didn’t come out until later in life, and what life is like for LGBTQ+ people from coast to coast.

Viewers benefit too, of course—both from this empathetic portrait of the trans experience, and from the banter between two of the best comedy minds of their generation. (Oh, and there’s also an original song written and performed by Kristen Wiig.) Will & Harper premiered to raves at Sundance, and Netflix promptly acquired it. That experience was bittersweet for Steele since, quite literally during the Park City, Utah, festival, state lawmakers passed a bill restricting transgender people from using certain bathrooms and locker rooms that correspond with their gender identity in government buildings, including public schools. This is the reality trans people face in increasingly large swaths of the country.

When I meet Ferrell, Steele, and Greenbaum several months later, however, they’re in much higher spirits. We’re at the Telluride Film Festival, where Will & Harper has been screening to more raves and bubbling Oscar buzz. Our conversation in a Mountain Village suite begins the morning after their premiere night, where Steele received a standing ovation.

Vanity Fair: How was last night?

Will Ferrell: Yesterday was a highlight of my professional life. Two things: The standing ovation for Harper, I love for so many reasons, for the right reasons because it’s just palpable, people’s feelings when they watch this movie. But I love for the wrong reason because she can’t stand it.

Harper Steele: I have to tell you, just over and over again, I think it’s fake. No one likes me that much. I just can’t stand it.

Ferrell: You’re wrong. You’re so wrong.

Steele: I can’t get past it, so those moments are always almost embarrassing. At Sundance, I had my arms crossed up on stage and they were clapping and I was like, “It sucks.”

Ferrell: We were all just being shuffled through the lobby and put in the car. I’m talking to an old high school friend who’s lived here for 27 years. She brought her family and a friend who was almost in tears because her brother had transitioned five years ago. She’s like, “This is my life. You don’t understand.” She almost couldn’t get the words out. Then I look over and there’s Bill Murray. I just heard this voice go, “Will,” but really quiet, and it’s Bill. He just goes, “Great job.”

Josh Greenbaum: I stole a few photos of Bill talking to Harper after the movie, and I think I got some of you as well.

Steele: He was very Bill-like. He just shook my hand and gave me a look like, “You’ve done a good thing.” He is a comedy hero, but when he hosted SNL, he kind of insulted me, so I’ve always had that there too. [Laughs] Thanks, Bill. But I did get a call from Kristen Wiig an hour ago. I was on the gondola and she got a lovely text from Bill Murray saying, “What a beautiful film. What a beautiful song.”

As you’re out here talking about it, people are continuing to encounter you all just as they did in the movie—it’s a unique extension of what the movie is.

Greenbaum: That’s my favorite part of this film. Will was just talking about the number of people who come up and share their personal story, their connection. A lot of times it may be a trans story, but it’s not always. It’s some way of like, “Oh, after I saw this film, I immediately called my best friend. I immediately checked in just to connect and reconnect.” I’m not a huge fan, as a director, of telling people what to take from the film. I know what I took from it, but I love that we made the film and now it’s yours. You hand it off to people, so to see that it’s having this continued life—the story is continuing, I guess of our road trip.

Ferrell: I usually do a really good job of making something and holding on to the feeling and not worrying about what anyone thinks, which is important, I think. But I literally had the BBC on today as I was brushing my teeth, and they had that film reviewer, the guy with the mustache, literally doing a live remote from Downtown Telluride. They’re asking, “What do you think the health of the movie industry is? What’s the slate like?” And he’s talking about how there are more docs this year than usual, and he starts to go, “There’s one documentary in particular…” I was like, “Yes. Yes!” And: “This exquisite piece on John Lennon.” And I’m like, “You’re a fucking asshole.” [Laughs] But I can’t go down that road. I’m like, “Don’t get wrapped up in that.” Then I went, “Oh, he doesn’t like it. He didn’t get it,” and then I was like, “What is wrong with me?”

Is that unusual for you, to be so affected by media coverage?

Ferrell: I’ve given that all away. There was a time where you’d get wrapped up in the opening weekend and you’d see the reviews, but I learned to really let go even at SNL. I’m so proud of this and we’re so proud of it that I’ve really found myself leaning in.

Greenbaum: There’s also another level I would assume in that it’s you, Will, not acting as a character. One of the highlights of making this film was when we had to screen the movie, and at various points our families all saw it. Will’s dad came to a screening. He’s a lovely, lovely man, and he was in tears after. He said, “It’s the thing Will’s done that I’m the most proud of, ever.” And he thanked me and said, “That’s my boy up there.” It really hit me. We all have a much bigger emotional attachment here, maybe, than to other things that we’ve made in the past.

Ferrell: Because it’s us.

Harper, are you leaning in as Will is?

Steele: I’m leaning in. We did learn this at SNL: You failed more than you succeeded. I’m not comfortable with failing—I don’t like it—but I’ve put stuff out there in the world and the bad reviews have come in. But this one, I have a lot of hope for it. I’m hanging onto a lot of hope that I wouldn’t really care about as much with something else. I want everyone to see it, so when I hear the bad review—which I haven’t heard yet—it’s like, “Don’t cut off an audience for me, because I need this to be seen.”

There’s a tremendous amount of education in the movie for people watching your journey. As you’ve shared it with people, have you noticed the audience learning rather basic aspects of trans identity?

Steele: 100%. The whole point of the film is not to be polemic or to be polarizing, but to help families, which are basically all of our families in this country—whether people want to acknowledge it or not. There’s a queer universe out there that they’re related to, and this is a great way for them to enter into that.

Ferrell: I’m golfing in LA with a guy who’s probably center-right and he brings it up out of the blue. He says, “My son’s gay, just came out at 18, and he told me about your movie. Tell me about it.” That’s that whole other side of the equation that we hope that there’s an audience for.

Greenbaum: We partnered with GLAAD on this film, and they were really helpful in giving us feedback as we’re bringing the film out in the world…. And Harper’s the fucking best. I guess you can’t say this, but she’s so honest and vulnerable and all the things you love about any person. So it’s not unknown, it’s less scary. She just wants to, as she says in one scene, “get to be in the world.” That’s what she wants.

Will Ferrell and Harper Steele at the Telluride Film Festival.

Paul Best/Getty Images

Transphobia is not exactly in hiding in this country right now. Have you encountered people resistant to the movie, even just its very premise?

Steele: No, actually. I mean, I’ve encountered it online. That’s where you’re going to encounter it the most. A lot of the anger directed at trans people is, for lack of a better word, subterranean. It’s people afraid to confront other human beings directly with this stuff. Politicians and press: Those are the two areas where I always blame the polarization and the anger happening. The press likes the clickbaits and the politicians like to get voted on by whatever contingency they’re going after. [In the movie] we have a run-in with a governor in Indiana who has voted in legislation against trans healthcare for youth. I don’t know how he feels personally. For all I know this person could have a trans kid. I mean, that would be horrific, but it’s not like he didn’t grow up around queer people. This is all absurd. JD Vance had a trans friend in college and now he’s got to appeal to whatever this red-meat world is. You’ve got to feed these people. But when we were out there, it was like, “Are any of these people this angry?”

Ferrell: Right. Are we making these people this angry?

Steele: Like it’s civil war. They made a movie about it! They’re making it sound like we’re one foot away from it, but if you go out there and drive around, which people don’t do who are talking about this, I’m not seeing it as much. Half the people I grew up with in Iowa were conservatives and, well, everyone liked everyone.

Ferrell: I’ll be curious if anyone approaches me once it’s out in the world. With any of the comedy films, if someone doesn’t like a movie, they just don’t say anything. They just go, “Oh, hey!” Or I run into that thing of, “My wife loves you.” I make the joke back to them: “And you are… 50/50?” [Group laughs] But this is interesting because it’s a totally different thing for me to be in: challenging subject matter, for some people. I’m just wondering if someone saddles up to me, like, “I’m used to your movies. Why did you make that? Or why did you participate in that?” But if they do, I accept the challenge.

Greenbaum: Harper said [the other day], I think she’s right, unfortunately, that there will be people that go, “I’m never watching his movies again.”

Ferrell: 100%.

Greenbaum: And you knew that from the get-go.

Ferrell: Exactly. I welcome it. If this is the last piece of press I get to do for any creative endeavor, well…!

It’s going on Netflix in a few weeks, reaching a very large, immediate audience—which is quite different, even, from a big theatrical release.

Ferrell: We embraced that reach. That’s a big part of it.

And you’re coming out right before the election.

Ferrell: Which is another thing we really pushed for.

Steele: I hope my guy Trump wins. [Group laughs] Me saying that might actually help the cause for the Democrats. Transgender writer Harper Steele loves Donald Trump.

What did you learn about the country in making this movie?

Ferrell: There are pockets of deep hatred—which, once again, I’ll always say is fueled by misinformation and not really stopping and thinking about it and asking questions. But I think folks for the most part just want you to live your life. Even if they have a super strong opinion, they’re like, “Well, that’s your business.” It’s all this propaganda and everything being kind of contrived for clicks.

Steele: Let’s not take away from the fact that there’s a lot of violent crimes directed at trans people.

Ferrell: Right, let’s not paint a sunny picture here. It’s definitely harder for people with less advantages than me to navigate the country. And there is still danger there. I would never want to not say that.

This is a documentary about a trans woman driving across the country, but it’s also, inevitably, about Will Ferrell, the celebrity, driving across the country. How did you approach that balance?

Greenbaum: As Harper will tell you, this was not the average trans experience. I know Harper wanted to go places along the way without Will. Certainly, I did my best to keep this crew as small as possible. We never let anyone know who was coming. because otherwise, you do invite the crowds and that’s not what we were looking for. But you have to acknowledge in any documentary work that cameras do change and alter any given situation.

Harper, as someone who’s about to become a significant public figure, do you have any hopes or plans for how to use that platform—whether creatively or politically?

Steele: I would love to take on more of an activist role. I’m political, but I’m not getting on any stumps anytime soon. I’d like to be more involved in the queer community in any way that I can. I resisted it and I was afraid of it and now I’m not. That’s just been a natural progression for me. That’ll happen and it’ll keep going, and then I’ll get more involved in things I feel strongly about—which is a lot of LGBTQ causes.

In terms of my writing, I wasn’t the most bro-y writer as a bro, which I’m proud of. I think I’ll stick to the plan.

Ferrell: You almost made fun of that style of writing, anyway.

Steele: Well, I did. Thinking of Eurovision—If you’ve ever seen a Eurovision, this is just a flat-out queer environment. And that was really important to me when telling the story of that film. Because I read an article… I’m babbling, I’m sorry.

Ferrell: Oh, we’re used to it. [Group laughs]

Steele: And Josh is like, “Oh yeah, no, she is babbling.” But no, I read an article right before we went to our first Eurovision from this queer writer who wrote a big Eurovision book, and what he said in this Times article was that Eurovision was what the union was supposed to look like—the freedom of expression and all the countries coming together in a much more friendly environment. That’s why I wanted to do it with Will. Before I was out, I knew I was trans, and I was looking at it going, “This is amazing.” My writing had already gone in that direction.

This interview has been edited and condensed.


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