Harper Steele Is Ready for Her Next Adventure

“Life on the other side, from my experience, has been nothing but joyful,” the former Saturday Night Live writer tells Bazaar ahead of the release of her new Netflix documentary with Will Ferrell

By Chelsey SanchezPublished: Sep 30, 2024 1:07 PM EDT

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Since driving from New York City to Los Angeles with a camera crew and Will Ferrell in tow, Harper Steele has made the trek across the country again. Twice. Only those times, she did it alone.

The cross-country voyage undertaken by Steele and Ferrell—who have been close friends and collaborators ever since they first met in 1995, working on Saturday Night Live—is at the center of Netflix’s new documentary Will & Harper. Together, the duo set out to visit places like Iowa, Indiana, Texas, and Arizona, rediscovering what it means to explore parts of the United States for the first time since Steele came out as a trans woman at 61 years old.

“It can surprise you,” she tells Bazaar. “The ‘F Biden’ signs and the Trump signs are there, and the Confederate flag and all the sort of signs that say: ‘This isn’t a welcoming place for liberals or liberal-thinking people.’ But that doesn’t turn out to be true.”

Instead, the doc shows there is a side to the U.S.—one that often gets buried in the bipartisan kerfuffle of political theater—that is open-minded and tuned in to human empathy.

Despite tense run-ins with Indiana Governor Eric Holcomb and patrons at a Texan steak house, Steele (who is quick to note that not every trans person is armed with the security of a Netflix camera crew and an A-list celebrity) found the experience only emboldened her to do two more road trips on her own, an endeavor she previously worried she wouldn’t be able to undertake again. “It’s given me hope,” she says. “It’s given me a little more confidence.”

A day before the documentary dropped on Netflix, Steele got on a call with me from Los Angeles, to chat about finding thriving queer spaces across the country, thrifting in the Valley, and seeing Will Ferrell cry for the first time ever.

Netflix

Will & Harper has been getting so many positive reviews and reactions since it first premiered at Sundance in January, and now it’s going to be released on Netflix and in theaters. How are you feeling ahead of the release date, knowing it’s going to be heading to a wider audience pretty soon?

I think I’m going to try to avoid thinking about it, because I don’t know the ramifications at all of what it means to go into 200 million households. You know what I mean? I think I was talking to Elliot Page, and he said something like, “Don’t pay attention to any of the comment sections.” And I’m kind of taking this to heart. I’m just like, “I don’t read good or bad reviews. I’m just letting it kind of happen.”

At the beginning of the documentary, you said, “I love this country so much. I just don’t know if it loves me back right now.” I’m curious to know how you think your perception of the U.S. might have evolved from before and after the trip, if it’s even evolved at all?

It’s evolved for sure. Part of that’s my evolution and not the country’s evolution. Part of it’s just my own projected fear about how I would be received in places. Maybe there is a learning that also goes on, that’s real, that I think people—despite what the press and what politicians and what Twitter is doing to us—I think we all would like to see civility and kindness return. I hope there’s a kind of longing for that. I think I felt it a little bit. I know in my home state of Iowa, it’s something that I think is there. It’s sort of the resting place. It’s been there my whole life.

Netflix

You went through a lot of different places throughout the country—Iowa City, like you mentioned, Texas, Indiana—and a lot of these places that you traveled through also happen to be places that are actively passing anti-trans legislation. Was there any specific reason why you chose this route?

No, the country is so vast and so wonderful in every area that this was almost based just on the weather. It was spring and I have to go through Iowa City, where I’m from, and there was that moment where we stopped by and saw my sister, which is something I wanted to do. But right after Iowa City, we went as fast south as we could down to basically Interstate 40. And I just wanted to be warmer. But again, I mean, there’s red states, blue states on any path across America.

It’s refreshing to see because there’s this stereotype that Middle America is inherently conservative. What’s really compelling is that the doc shows that, not only can we find tolerant and accepting people anywhere, but you also find queerness everywhere. The scenes with you and Dana Garber—the woman who is part of the trans community in Illinois—those moments really help show how universal queerness is or how queerness and transness can thrive if given the resources and support system to do so.

Oh yeah. There’s a trans woman, Samantha Allen, who wrote a wonderful book called Real Queer America. She traveled around the country and she was mainly interested in going and finding queer spaces, but they’re everywhere. They’re all over the country. Even where we ran into some what might’ve felt like a lot of intolerance or possibly just sort of some judgment—I know that Amarillo [Texas] has a queer community. There’s queer people everywhere, obviously. So that’s not even, for me, the issue. … There’s liberal people in conservative places and conservative people in liberal places. So we tend to kind of codify these things, and it’s unfair to all the people out there. And often I find conservative people also are very accepting. So it’s just a mix.

Was there anything that surprised you during your trip?

Well, to be honest, I don’t think I've ever seen Will Ferrell cry. We generally are laughing. We’ve had serious conversations, but I don’t think I’ve ever seen him cry. So I think that was a bit of a surprise. [Laughs.]

will harper to r will ferrell and harper steele in will harper cr courtesy of netflix

Courtesy of Netflix//Netflix

Will’s presence on this trip, he almost acts as a kind of protective force. Not only is he your cisgender male friend, but he’s also Will Ferrell, The Celebrity. I think fame can be kind of insulating in that way. But there is also a pivotal scene in the documentary where you decided to enter a bar by yourself and you had Will wait outside for you. Why was it important for you to go ahead solo in that moment?

Well, certainly that’s the kind of place that I liked to run around in while I was trying to pass as male. So that was part of the doc. I needed to make sure that I was okay in the same spaces that I always wanted to be in. I mean, I don’t want to give up that love of that part of America. So it was important for me to go in there. Will and—certainly to some degree—a camera crew change the dynamic no matter what you’re experiencing.

That said, I was with a camera crew and it makes it a little easier. I’m not positive I yet have the confidence to walk into that kind of space by myself without a crew. Certainly Will Ferrell changes the dynamic in any place you’re going to, ’cause everyone wants to be friendly to Will. As I pointed out a few times, there’s [Indiana Governor Eric Holcomb] who has passed some anti-trans legislation, and I find to some extent he’s given up his principles to take a photo with Will. I think that that sort of demonstrates what Will can unite. He can bring people together. He’s beloved by a lot of people. Again, I don’t want to be so aggressively angry at this governor. I don’t know his principles. Politics sometimes covers or determines how people act, and maybe it’s not how they really feel. So I can’t judge him completely on that level. But yeah, Will changes the dynamic. Cameras change the dynamic, and there’s other things that make it slightly different for a lot of trans people that aren’t privileged, that don’t have the money to zoom out of there in a car. There’s all kinds of ways that dynamic wasn’t exactly a trans experience. It was important to me to go in there alone, though, for the reason that these are places that I love.

Have you gone on a road trip again since filming?

Yes. I’ve been back and forth twice. That bar, maybe I wouldn’t go into at 11 o’clock at night or whenever we were there. But I’ve been to the truck stops and diners and a lot of places, so I’ve gained a lot of confidence and a lot of trust in how people are going to respond.

For fellow trans people who may be facing a similar situation, who might be coming to terms with their gender identity later in life, would you have something that you would want to say to those people who are watching the movie?

Well, I hope the movie speaks to people who are struggling and they can share it with the world [and] the people that they are worried about. Will Ferrell has such a wide audience that maybe this will allow people in on a conversation for those people who are either thinking about coming out or who might want to. Life on the other side, from my experience, has been nothing but joyful. I can’t vouch for everyone’s experience, but for me, it’s been nothing but joyful. And I can only hope that for anyone who’s trans, once you’re fully out and sort of in front of the world the way you need to be, there’s just no comparison.

toronto, ontario september 11 l r harper steele and will ferrell attend the premiere of will harper during the 2024 toronto international film festival at roy thomson hall on september 11, 2024 in toronto, ontario photo by jeremy changetty images

Jeremy Chan//Getty Images

Harper Steele and Will Ferrell attend the premiere of their documentary at the 2024 Toronto International Film Festival.

Harper’s Bazaar is a fashion magazine, so obviously we’re going to talk about fashion. Could you talk to me a little bit about what that’s been like for you, getting to build your own style preferences from the ground up?

I’m a thrift-store queen and I’ve been one for my whole life, so style and clothing are seriously—with a lot of trans people, honestly, but for me—one of the most important things to me. It’s a fluid situation now. I’m changing. I was given a Staud dress for a [Toronto International Film Festival] premiere that, when I put it on, it was sort of [like] walking on air. It was incredible. The Rodarte sisters have created two dresses for me. So this is really a dream come true in a way, but it’s not going to take me out of my thrift store. I’m going to keep rummaging through there, looking for fun, weird things to wear. And obviously I’d like to work on my accessory game. That’s where I’m really kind of failing. So any advice Harper’s Bazaar has for me, I will take.

I love that you said you’re a thrift queen. For thrifting in L.A., I’m from the Valley and—

Yeah. Oh my gosh, you know then. You know. Those are the best stores in the world. And I’m a road person, so I know where all the great thrift stores are and nothing beats the Valley.

The Valley’s great. Living in New York City, the thrifting game is not the same as it is in L.A.

It’s fallen off. It was good back in the ’80s, but not now.

Is there anything that you're getting to learn more about yourself as you’re going through this style overhaul, essentially?

Yeah. Because style is so desperately important. You know what I mean? This is probably just true for all people, but I can speak to sort of my trans experience. You are trying to get more and more comfortable in the gender that you want to present, and so the style has just been such a wonderfully evolving [process]. Again, I just love discovering something new.

This is particular, but I found a 1980s Frederick’s of Hollywood vest, and it’s kind of lingerie-looking. It’s a little thicker than that. And I put it over a different piece of clothing and I just fell in love with this look suddenly. So, you know what I mean? Like I just love playing with clothing and sort of creating my sense of self through that. But yeah, it never ends. To me, that’s a joyful part of it also. That’s the thing. It’s like you’re sitting there in my dead self wearing a pair of J.Crew khakis and some dirty bucks and a button-down shirt for 30 years of my life. It is like a jail sentence. And so you get this opportunity to finally live the way I need to live, and there’s just so much freedom there. And I think fashion, it equals freedom.

Have you gotten a chance to wear the diamond earrings that Will got you yet?

Oh yeah. No, I’ve worn those. I wear ’em at certain premieres, and then I take ’em off because I lose studs faster than any human on the planet, so.

All right, Harper, my last question for you—I think this is the hardest one yet.

Okay.

What are your tips for the perfect cross-country road trip?

Well, it takes a certain kind of friend, but you should always try to bring a friend. There may be a few arguments here and there—there weren’t with Will and I—but take that friend that you’re going to have fun with, experience life through their eyes as much as yours, and get the mixtape right—although now it’s a Spotify list—get that right. And bring a cooler. You have to bring a cooler.