Saturday Night Live writer Harper Steele came out as a trans woman in 2022 at the age of 61. Her friend of 30 years Will Ferrell had questions. So what else to do but jump in a van, cross the US, and make a documentary about it

I’m not trying to exploit our friendship,” Will Ferrell says to Harper Steele, his longtime collaborator. “I’m not trying to exploit your exciting, wonderful, joyous news.” His tone isn’t defensive; Steele, sitting beside him, smiles at this echo of a conversation they’ve obviously had many times before. Really, Ferrell is answering my question: when one of your closest mates comes out to you as a transgender woman, how do you wind up making a film about it?

The film in question, Will & Harper, is not a typical one for Ferrell, best known for his elaborate goofball antics in the likes of Anchorman, Zoolander and last year’s megahit Barbie. It’s a Netflix documentary, for one thing, and one in which Ferrell, albeit on screen throughout, isn’t quite the focal point. That would be Steele, former head writer of Saturday Night Live (SNL), and close friends with the actor since they both started work on the long-running sketch TV show in 1995. Two years ago, aged 61, she wrote to Ferrell with some news: after a lifetime of unspoken gender dysphoria, she was transitioning to become the woman she was always meant to be.

Ferrell was immediately supportive; he also had a lot of questions. Such conversations aren’t best had from opposite coasts: the actor, a born-and-bred Californian, was based in Los Angeles, while Steele was back in New York. What about a cross-country road trip, Ferrell suggested, where they could talk things through in their own time? And what if they filmed it too?

For a few months, Steele ruled it out. “I don’t like being on camera, so my initial decision was just based on that,” she explains. “But transitioning is a process, and so I started to feel a little more comfortable with who I was. And the fact is, there was a lot of legislation and bills being introduced across America that were very restrictive and very damaging to my community. And I thought: well, I could use this celebrity who reaches a much wider audience than I would normally be able to get, to reach out to the people who are passing these bills, maybe.”

The resulting film is a kind of freewheeling real-life buddy comedy, as the two pals bicker and banter in a rickety vintage station wagon headed west. Their easy, candid comic chemistry plays out off screen in much the same way it does on camera: sitting in a high-end London hotel room, they often talk to each other as much as they do to me, finishing and correcting each other’s sentences, or interjecting with sudden stray recollections.

As well as a breezy friendship study, however, the film works as a thoughtful examination of the possibilities and limitations of celebrity allyship. In parts of the US still hostile to trans rights, Ferrell’s household name and face makes him a kind of middle-man, encouraging conservatives into sympathising with an identity they may not accept or understand. On the flipside, a Hollywood spotlight can invite as much hostility as it deflects: both scenarios play out in Will & Harper, though the pair’s companionship sees them through the worst of it.

“None of us wanted to make a quote-unquote ‘political’ film,” says Josh Greenbaum, the documentary’s director, though he also says it’s “not a coincidence or a mistake” that it’s being released in an election year, where trans rights are heavily at stake. It’s the human dimension of the film’s friendship study that he hopes will connect with warier viewers. “I think when you sometimes [go political], half the audience turns off because they think you have an agenda. But it’s a very personal, intimate story between two friends. I wanted to keep that front and centre.”

Still, for Steele, the film was an opportunity to demonstrate the value of active support at a time when the trans community needs more than passive sloganeering and social-media endorsement to defeat widespread prejudice. “I think there’s a kind of Facebook version of allyship,” she says, “which is people saying: ‘I support you and I love you,’ but what does that mean?”

“I know a lot of influencers: not social media influencers, but people with a lot of influence. I wrote to them to say: for any of your trans friends, remember to gender them correctly, because what that means is not necessarily that you’re protecting that person. You’re telling other people around you that this is the way we need to act. These people have spread so many things in the world. Comedy, opinions, ideas. Why not spread this one for everyone? That’s allyship to me.”

For Ferrell, meanwhile, the film allowed him to demonstrate that such allyship still affords room for error and correction: many of the conversations he and Steele have on their trip see them re-establishing the terms of their friendship in a judgment-free space. “It made it a safe arena for me to stumble my way through,” he says. “I think it’s important for the audience to see that I’m searching, I’m stumbling, because I want to say things in the right way and I haven’t caught up to speed as to the right way to engage. And Harper takes the curse off of it by saying: ‘Just spit it out. It’s OK. You’re my friend, and I allow you to kind of make mistakes.’”

Comedy remains their default language, even when discussing vulnerable personal matters: even during a bittersweet visit to Harper’s childhood home, the edge is taken off by a gleeful bit of unicycle slapstick. I ask Steele if her transition has changed her irreverent approach to comedy writing. Does she still believe that anything goes? “Sure,” she says, “but not for me. I mean Netflix is airing our film, but also has comedians saying things that I wouldn’t say about trans people. I’m not a police person. I’m also not saying that I think comedy should be able to do all this stuff. But I’m not going to be able to stop it, and it’d be absurd to try.”

“I do know what laughter can do to harm people I knew,” she adds. “It harmed me. I watched the show M*A*S*H for my entire teenage life. I had to watch the character Klinger in a dress get a laugh every time he entered a room. That’s what I grew up with. So I know how damaging that can be.”

Ferrell admits some of their SNL output wouldn’t fly today. “I look back at some things and I’m like, ‘Oh yeah, I would never do that again,’” he says. “But I think, for a lot of the stuff we’ve created, we’re not into punching down. We love silly and we love absurd.”

The decision to make the film a cross-country journey was not just cinematically motivated, nor a political outreach attempt. Before her transition, the Iowa-born Steele regarded the dive bars, diners and sports grounds of middle America as comforting spaces, and would routinely drive across the United States to observe and converse with the people there. As a trans woman, however, she no longer felt welcome or secure in many of the venues that once made her happy; in the film, Ferrell acts as her wingman, effectively reintroducing her to her happy place.

“The film is not a representation of a trans person’s experience going across America, because I have Will Ferrell in my camp, so obviously it’s changed for me,” Steele admits. “The point I wanted to make with the project is: why shouldn’t I be allowed to love and experience the thing I’ve always loved and experienced? My favourite thing to do is to get out on the road. I’m Harper Steele now, but it shouldn’t make any difference.”

That anxiety isn’t limited to the US, either. When I interview them, Ferrell and Steele have recently returned from a trip to Yorkshire to see a Leeds United match – Ferrell being a minority stakeholder in the club. I ask Steele if she felt the same trepidation that, in the film, she describes around sports venues. “American football and football over here share a kind of maleness and a kind of toxicity that I’m a little bit wary of these days,” she says. “So taking the train up to Leeds was a decision I had to make. I had a wonderful time. But I can’t tell if your standard British football fan is going to be excited about a trans person sitting next to him at a game.”

That tension can be felt in Will and Harper, too, though sometimes the star misreads the moment. One filmed set-piece in a Texas steakhouse was meant to be light comic relief. Dressed in his Sherlock Holmes costume from 2018’s misbegotten Holmes & Watson, the actor sits opposite Steele to begin a supersized steak-eating challenge, though they soon sense the room turning against them: dehumanising tweets in the wake of the stunt prove that Ferrell can’t always, in Steele’s words, “take the heat off” her.

Why shouldn’t I be allowed to love the thing I’ve always loved? My favourite thing to do is to get out on the road

Harper Steele

The next morning, Ferrell admits to feeling he let her down. It was a pivotal moment, says Greenbaum: “That was a learning point, certainly for Will, that not all attention is good attention, particularly for those in the trans community. It was an unforeseen error, but I didn’t want to then sweep that under the rug and not include it. A huge part of the trans experience is that there is just a massive amount of hatred, a lot of it online.”

Meeting trans people is the first step toward opening minds, says Greenbaum, in which case he hopes the film will act as a kind of gateway. “Seventy per cent of people don’t directly know or think they know a trans person,” he says, citing a statistic they were presented with in their research for the film. “So they get what they get from the media, from politicians. So if they don’t know anyone, now they’ll know Harper. And she’s funny and charming and complicated and just all the things you would want to represent the human side of a trans person’s experience. Then maybe the politics will follow.”

For Ferrell, it was important that they never set an objective for the film while making it – a contrast to what he describes as the “pressure-cooker environment” of his and Steele’s days on SNL. “This will just be whatever it’s going to end up being,” he says of their mindset going in. “So if it happens to be funny, if none of it happens to be funny, it will find its way. It was great to not have, in a conventional sense, a shooting day where you’re hoping this scene works, or wondering why it isn’t working. We made it all the way to Santa Monica, and Josh said: ‘I think that’s a wrap.’ And then we walked back to our car going, ‘I don’t know if there’s a movie there. But that sure was fun.’”

I ask Steele if it occurred to her, while making the film, that she’d be a first trans acquaintance for legions of Netflix viewers. “I wasn’t really thinking about it. That would be weird,” she says. “They gave us some fact that more people have said they’ve seen an alien than have seen a trans person, which I find it a little hard to believe. I’m travelling across America. Every family has queer people, whether they acknowledge it or not, and the trans community is a part of the queer community. I like to affirm that.” She pauses. “So maybe it’s possible people don’t have trans people in their lives. But I believe they will.”

Will & Harper is on Netflix from 27 September.