'Will & Harper' navigate transition and friendship in a cross-country road trip

A few of years ago, Will Ferrell found out that his close friend and former Saturday Night Live writing partner was coming out as a trans woman named Harper Steele.

"It was a complete surprise, knowing Harper for as long as I did, ... I didn't see it coming," Ferrell says. "And then you fall back on, What do I do? What's the right thing to say? How should I say it?"

The new Netflix documentary, Will & Harper, follows Ferrell and Steele as they drive from New York to California, talking about their friendship and Steele's transition. Along the way, they make various pit stops, including to a dive bar in Oklahoma, an Indiana Pacers basketball game and a steakhouse in Amarillo, Texas — some places that Steele fears would be unsafe for her to visit alone as a trans woman.

"They're wonderful places where all kinds of humanity, all kinds of Americans exist, and I love ‘em now as much as I did [prior to transitioning]," Steele says. But, she adds, "It's always a little bit more fraught [now]. And I don't know if it's because I'm a woman or if it's because I'm a trans woman. I can't quite discern that at this point."

At the Texas steakhouse, a crowd gathered to photograph Ferrell, but the friends soon felt the energy in the room shift. Their discomfort was confirmed when they later saw hateful and transphobic social media posts from people at the restaurant.

"I just carried a little bit of the guilt and the burden of like, Why did we even go in there? There was no need to," Ferrell says. " And yet I think it's a powerful part of the film. ... It turned out to be kind of valuable for me to feel that and to see that that kind of hate does exist out there for the trans community."

For Steele, the film was less about the cross-country journey and more about her decades-long friendship with Ferrell and an exercise in vulnerability: "I was just looking at [it as], this would be an interesting way to have a conversation about this subject with someone that I care about."

Interview highlights

On coming out as a trans woman later in life

Steele: It wasn't a decision about right timing. It was a decision about living in misery and not wanting to do that anymore. So it just took me a long time to finally give up — and I do think of it as a giving up. I just collapsed into myself and found the other side and it's been so much better. ...

I've discovered that vulnerability is truly a really powerful superpower. I'm not calling that a feminine trait. … For me personally, to walk out of my house in a dress was a very vulnerable and raw moment, and what became of that moment was pure joy. So trusting vulnerability more has been something that truly has been helpful to me.

On Ferrell's response to Steele's coming out

Ferrell: You get an email from a friend announcing this kind of dramatic news and I didn't really stop to think how much pain, how much anguish there was to get to that point, how much thought it took to write that email. ... This was something that obviously was a part of her this whole time, and the sadness of her kind of putting it aside, kind of squashing it down, but then the courage that it took to get to that point where she was like, "Enough, I'm going to give up the fight." I just learned how incredibly strong she is, how articulate she is. She's always made me laugh. … And a lot of people have come up to us just saying, "It's just nice to see friends stick up for each other." I think that's what we're most proud of about this whole thing.

On correcting people who misgender her 

Steele: When it comes to friends, I sort of feel out the situation, If people are misgendering me and it's annoying me, then I correct them. If it's friends, I correct them in my funny way. But I don't like my friends to feel on edge around me talking about my transition or talking about who I am now. I don't want them to feel that. So I'm not interested in nailing everyone around me.

Ferrell: What's happened with me, though, as I've become more comfortable with it and it's become second nature, I've found a certain vigilance when we're out together and someone by chance does misgender Harper, I'm like, “Excuse me, no …  She. Her.”

On hugging 

Steele: Will has pointed out many times that before I transitioned, hugging was not in the equation. Will would hug me knowing that I would go stiff as a board and just hate it and now I'm a hugger so I will accept all hugs from good friends between men and women, between anyone. … It has meaning. It's touch, it's "I care about you" and that's wonderful.

On being aware of her face more now as a woman 

Steele: Hollywood, in the business that I work in, we value faces. Somehow Will Ferrell slipped through.

Ferrell:  Somehow. … But I'm going to get some work done after this.

Steele: We value faces. And so I like the middle of the country because it's me. There's people out there, like real people.

Ferrell: Well, men are lucky in that —

Steele: You can be ugly.

Ferrell: You can be ugly. And we can look distinguished. … I'm in comedy, so it's not critical for me to worry about that. But it's not my nature anyway. And, in fact, I remember doing a Q&A somewhere, and one of the questions from the audience was, "Why are your eyebrows so white?" I said, "Because I have gray hair. It's called the aging process." So I'm almost a poster child for not doing anything in that regard.

On not wanting to change her voice

Steele: I think it's important for me to tell people that I am first a human being and second, a trans person and third, a woman. So I'm not that overly concerned about passing. I like being gendered correctly, I do. But passing is something that a lot of trans people want and need and should have if that's what they want. But for me, it's not as important. I would love to be prettier, but I'm not sure I'm different than a lot of women in the world. And I wish I had been born with a different voice. But this is who I am. But these things are fluid, too. I could tomorrow start voice lessons. I doubt I will, but who knows? Your gender is a slippery thing for some people, and I'm happy about that.

Lauren Krenzel and Anna Bauman produced and edited this interview for broadcast. Bridget Bentz, Molly Seavy-Nesper and Beth Novey adapted it for the web.