Women Who Travel Podcast: Harper Steele on Navigating America in 'Will & Harper'
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Lale Arikoglu: Hi, there. I'm Lale Arikoglu, and this is Women Who Travel. Today, we're going on a road trip and exploring the story behind Netflix's documentary Will & Harper. 30 years ago, one Saturday Night Live writer and another actor became lifelong friends and collaborators. They are Harper Steele and Will Ferrell. In 2022, Steele came out to Ferrell about her gender transition.
And soon after, they decided to embark on a cross-country road trip to talk about whether or if or how their relationship might change. And I am so excited to have Harper on the show today to talk about that trip. You are, I think, in a hotel room right now. Where are you? Are you traveling?
Harper Steele: Yes, I am traveling. We're still showing the film to audiences and talking about the film, which I love. And I'm in New York City overlooking Central Park right now on a beautiful, beautiful, crisp, slightly too cold, sunny day.
LA: It is really cold outside. I stepped out this morning and was like, are we actually going to get a winter?
HS: No, I like this. I was unprepared too. This was a little bit of a detour coming to New York and I didn't know.
LA: When did you start having conversations about embarking on this trip with Will and how did the idea come about?
HS: Will and I during the pandemic, we hadn't seen each other in a long time. And I had written this letter saying I was going to come out and present as a woman and, that's the wrong way to say that, to live my life authentically. At any rate, I wrote this coming out letter, but I wasn't able to see Will. And then we ended up in Will's backyard still during the pandemic, and we were sitting around.
And he said, "How are these road trips..." Which I'm known for. I travel across the country back and forth many times. "How are these trips impacted by this new sort of decision?" And then he just out of the blue said, "What if we took a road trip and we filmed it?" And I'm very camera shy, so I said no. And then I sat around in my house for a while and thought about it, and a couple of factors.
One of them was that there was a lot of legislation and legal battles going on across the country and a lot of state houses that were fairly anti-trans, and I just thought there was something positive to do here, especially with a beloved actor like Will Ferrell.
LA: When Will asked you that question about how road trips, which clearly is a form of travel that's been important to you throughout your life, had you considered that answer before or was that a new thing for you to suddenly think about?
HS: Yes, I knew the ramifications of it and also the projected fear of it that I had already experienced, but it was fairly hidden. When I first started doing it sort of as myself, I would get scared. And then if I had to go to a gas station or a truck stop, I would throw on a pair of sweatpants. It was always an upsetting moment right at that moment where I had to decide to give up who I was just to go into a restaurant. And so right before Will and I did it, I went back and forth once.
And that time I said to myself, I'm not going to do that because now I've come out officially. And yet I will say that I still was quite, what's the word, fearful of spaces out there. Maybe I shouldn't have been, but it was early days and I was projecting a lot of fear. So if I had a decision to make, like I need to go to use a rest stop bathroom, I might say Dunkin' Donuts has these unisex solo bathrooms, maybe I'll look for a Dunkin' Donuts. So I was making decisions based out of fear, I think, from the beginning.
LA: That's a lot of anticipating. That Dunkin' Donuts example, which I'm sure that many trans people can relate to, is you have to add a layer of planning to a trip that other people may not have to consider.
HS: Well, what I have learned from my female friends is that built into being a woman is a layer of planning as well just in terms of safety and traveling at night and the kinds of places you stay, all these things I didn't consider back when I was passing as a man. It was a bit of an education in that regard. And then yes, because there is some real and definitely much more perceived hostility towards trans people, it did add an extra layer I think. But I don't want to take away from what I think women probably experienced traveling alone across the country all the time.
LA: I mean, I'm coming into this as someone who grew up in the UK. So the idea of an American road trip is just so big and bountiful and weird and adventurous. It captures my imagination so much. What is it that you love about those trips?
HS: America's so vast. People joked, "I want to see a sequel to this. Maybe you should try England." Well, that's a two-day road trip.
LA: I was going to say, yeah, it won't take very long.
HS: That doesn't help me. No, it's so vast and there's so many areas to explore. I'm not really much of a continental or world traveler. There's something stressful about planes for me. I love traversing this country so much that it's enough for me. It's not that I don't like Europe or exotic places outside of Europe. I don't know. I've never been an island person. I do really find myself out in the middle of the country.
LA: It is a movie about friendship, and the dynamic between you and Will is so beautiful to watch and enjoyable. I imagine when you first got in the car, it was just like standard catching up banter. I mean, in the documentary, you pick Will up from the side of the highway and he's in this garish jacket. And it's all very funny. How long did it take to break things open, so to speak?
HS: Yeah, there's two forces at play there. It's any friendship that needs a little time to warm up again, but also the cameras make it a very constrained and weird environment, even for Will, who's not used to having a camera on Will Ferrell. He's used to having a camera on one of his characters. So the director Josh Greenbaum had said, "On day two or three, you'll forget these cameras are here," which we did not believe at all, but it did turn out to be true.
So it took at least three days before we were just comfortably having conversations. When you're with someone in a car like that, it gives a great rhythm to a conversation. There's peace and a pacing or space to the conversation because you can be looking out the window at nothing, but also talking about the most serious things, which car conversations generally do get a little more intimate just because it's a forced intimacy.
So it's a really fascinating way to go through the world. I would recommend it for any deep friendship to be in a car because, I don't know, I just think that that's a great way to be intimate without having to stare at each other. It's very helpful sometimes to not have to look someone in the eyes. Will and I were actually shocked.
We thought we would be done talking by about Pennsylvania, and we didn't stop talking until we hit the beach in Santa Monica, which we both were a little surprised by. And now Will and I, the way we converse is trying to make each other laugh. That's basically our love language.
LA: I mean, when I think of some of my closest relationships, when the other person is struggling or we're having an emotionally difficult conversation, I think my instinct often is at a certain point to turn into the court jester and that's not always helpful. And being in a car together with this very focused purpose for why you're doing this trip must have at points stopped you from doing that.
HS: Well, I think we reached some emotional places that were a little unexpected for both of us. I joke. I mean, it's halfway the joke, but it's the first time I've seen Will cry, and I have known him for 27 years.
LA: After you pick Will up, it begins with your two children in a diner.
HS: Yeah, I think that was a good place for us to start just so that Will could get a sense of the emotional backdrop of what it means to transition inside a family as well and how much love there was I think for all of us and how much concern there was. Both of my kids, they're smarter than me. I think that was neat for Will to see. Yeah, that was a good starting point as far as I'm concerned.
LA: After the break, we talk about some of the many highlights in the film. You're back with Women Who Travel and Harper Steele.
HS: Will has never driven across the country. I've done it more than truck drivers. So we sat down. And we just thought about some things we wanted to achieve, and one of the bigger ones was to go and talk to my sister in Iowa City.
LA: It sounds like you always knew you wanted to go home and see your sister at some point. That was always going to be part of this journey.
HS: Yeah. My family in general has been very accepting, which can be unusual for a lot of trans people, sadly. I don't know, I think I just wanted to acknowledge what that looks like, not just for me, but for other trans people or actually just more for other people with trans people in their families. What does it look like to be an ally? And my sister I think defines it. I mean, when I sent the letter out, she didn't really send anything back right away except, "Oh good, I've always wanted a sister," and that was it.
And then we talked later after that, but I think that just demonstrated the speed and the love behind that moment. And so going back to my city as my true self to me is very empowering. And I have this feeling all the time of stepping into places I once haunted now as myself and feeling this overwhelming joy. I would say by the time we got to my sister's, Will and I were pretty comfortable talking about anything, but naturally things came up after that that I think were fairly intense and I think make the movie not just funny, but useful, interesting.
From New York to Iowa City, there's a few routes you can take, but basically you're stuck on 76 or 80 or one of these highways that goes across the country that's going to end up in Iowa City. And it was also wintery. It was still late spring, and I hate cold. So as soon as we got out of Iowa City, we went south. And Highway 40 is one of my favorites because there's long stretches of nothing out there, especially in Oklahoma and West Texas.
LA: How did you plot out where you were going to stop on the route and how much was you and Will figuring it out together and did you have certain places that you were like, "We've got to go there?"
HS: Yeah, so I think it was just based on a few things. And then there were little logistical things like the basketball. We had to hit one where they were playing a game. We wanted to do a basketball game because Will and I had a lot of history going to basketball games before I transitioned. Basketball is something I've loved my whole life and it's mine. It's mine as much as anyone else in there.
So I think it was important for me to walk into that space not being afraid because I don't want to be afraid in the kinds of places that belong to me as much as they belong to anyone else. And I would say that about the dirt car racing track or any of these places that are deemed bro-y are spaces for all Americans. And the more we challenge that, the better we're all going to be off, I think, just by allowing everyone in.
LA: The basketball game I found as a viewer quite hard to watch at the end with the governor.
HS: Yes.
LA: When you're looking back on that now, how do you think about it?
HS: When we met this governor at the basketball game, we were told, "Oh, it's the governor." He comes over to talk to Will and asked us what we're doing. It's a silly moment if you slow it down, but Will, "We're going across the country and this is my trans friend. And we're just going to all the places that she used to go to before." And he gives a kind of like a, I don't know, perfunctory little like nod.
But after the fact, you can see me in the documentary I'm on my phone because I can't keep up with every governor of every state and what their politics are with trans people. But this particular governor had signed a bill that restricted trans healthcare for youth. And had I known that before or had Will known that before, I don't think we would've engaged in that conversation at all, unless we thought there was a teaching moment, but I don't think that's the environment for that, a basketball game.
So I don't think we would've talked to him, but we were ambushed. And that happens with Will a lot because everyone wants to meet him. Every stripe, every kind of human being wants to meet him. So that was the backdrop for that moment. It's shameful how a politician with a voting record in certain ideology will give up their principles to go take a photo with Will Ferrell.
We had a tense moment in a Texas steakhouse. We were in a Texas steakhouse that we had decided might be a funny, silly place to go because we had seen a sign on the way up Highway 40 outside of Amarillo that said eat this big steak in an hour and you can get it for free. And it's a giant piece of meat with a bunch of sides that Will kept complaining about. It was going to be funny.
We didn't realize we were going to be on a stage. It quickly became a kind of fishbowl environment where there was a lot of people, which is always true with Will, taking photos of Will. He was also dressed as Sherlock Holmes, a thing that we used to do all the time to each other just to make the other person laugh.
LA: That he had packed for the trip as well.
HS: He had packed the Sherlock Holmes thing. It was something he had done on a previous bar night that we had had, because we used to do this all the time, show up at a bar and try to show up in a different costume or something. If you're trans, you kind of have a radar, but the room felt very judgmental, and it started to get very claustrophobic in there.
I think I was beginning to feel fairly uncomfortable, and I think even Will said he's been in a lot of fishbowls before where people are surrounding him and taking photos, but there was something about the air in there. I do like it. I just refrain from saying the place was hostile because I don't know all the people that were in there. There may have been queer people in there and I would hate to be judgmental against a giant group of people.
But the tweets that we saw afterward that came from out of that environment definitely demonstrated a kind of hostility towards me. I like a decaying America too. I don't like it because I'm happy that it's decaying. I like it because it evokes... I don't know. I see that when I travel through the country, I see these decaying places and I think it's almost metaphorical for the sometimes moral decay that's going on. Again, I'm waxing too philosophical because I also just like to see a defunct old red brick building.
LA: Yeah, I feel like there's a lot of setting up camping chairs in parking lots at the side of the highway. Why were you choosing some of those locations? You could have been in the Grand Canyon really in front of some wild landscape, but it feels like almost that wasn't the important thing.
HS: No, no, no, no. I think people miss so much of the beauty in America looking for the treasures that we all know about or the tokens that everyone tells us we need to see. And I'm not saying that they're not beautiful. The Grand Canyon is quite beautiful and everyone should see it. It's that there is beauty in a Walmart parking lot, and there's definitely beauty on the side of a highway in the middle of nowhere. I like showing that to people when I take other people out on the road.
LA: Kind of thinking of that reference to the Walmart parking lot, what is the beauty you see there?
HS: Yeah, I don't know. Just walking into an artwork and saying, "How does it affect you," I guess, or a museum and looking at a Jackson Pollock or something and go, "What do you see that's beautiful in that?" I'm looking at a big chunk of my country in a Walmart parking lot.
And yes, the different kinds of cars, the people, the kinds of people that are there. Sometimes I'm talking to them, sometimes I'm not. And sometimes they're just in these excerpt, suburban locations out on the highway that also jus... I don't know, they just seem... It's a landscape that I don't think people really recognize, but it's so prevalent and everywhere.
LA: Coming up, traveling the world for screenings and festivals and seeing the audience reactions. Back with Harper Steele and what it's like now the movie's been watched by audiences across the world. It's amazing that you're still traveling and talking about this. I think it shows its reach and how many people have connected with it in different ways. It premiered at Sundance back in January. It's been nominated for a bunch of awards like the People's Choice Award at the Toronto International Film Festival. We're at the other end of the year. What impact do you feel like this film has had?
HS: One of the joys that I'm experiencing is people have been coming up to me on the street and saying they've seen the film. I'm not vain. It's not about that. I'll get into these conversations with parents who either have queer kids or queer kids with parents, and then they'll say they watched it together and it's the best conversation they've had in years. So if that's what comes out of this film, then that makes me proud.
I'm glad that that's revealed itself over the last year. The film is not very political. It's fairly benign. It is political obviously and it's subject matter and who I am, but we're not very strident in the film. It's a funny movie. I hope people understand that. It's Will Ferrell and me, and I'm funnier than Will, so imagine that.
LA: How do you think your friendship changed after all of this driving and these emotional intimate conversations together?
HS: We had a good friendship, but I think we had a deeper friendship and I think that's the value of a road trip, honestly. I think if you have a good friend and you have the time and maybe they're going through something, it doesn't have to be a transition, by all means, any kind of road trip, three or four days just in a car with someone, it just opens up an opportunity to listen and talk to each other. And I think that's what came out of this for Will and I. And yes, our friendship has been deepened, I think.
LA: You meet so many people on this trip, so many different types of people and different characters, and there are a lot of positive interactions, or at least they appear so, as a viewer. Did you walk away feeling like most of your interactions, and they're not all positive, that's for sure, but did you feel like most of them were or there was something about human-to-human connection in travel and traveling around the country that felt hopeful?
HS: Yes, 100%. I would say I'm not positive of how that really played out because I was traveling around the country with Will Ferrell, who is beloved literally by everyone. So those interactions might've been different had I been alone. The hopeful side of it is I don't really believe that entirely. Yes, definitely some of the reactions would've been different. Who the fuck is this person is fair enough when you're not with Will Ferrell and maybe even more hostile like I don't like trans people.
But I do think that most of the interactions I have, and I've been back and forth across the country since the documentary, I find that people are willing to talk to you or willing to be nice. I also tend to go to places where I feel there are possibly disenfranchised people or people that are not so settled. So I go to a lot of thrift stores. And in those conversations in those places, I'm talking to people who could be there for a variety of reasons, but they're in a thrift store.
We all have a community from the beginning when you walk in. I find a lot of comfort in places like that as in dive bars. When you're in a dive bar, there's lots of reasons to be in dive bars, but one of them is just a search for community, unless you're going there angry at your husband and you just want to drink by yourself, I don't know.
LA: I feel like a dive bar for me often ends up offering a real cross section of a community or of people who live in a place, like you said, looking for community, and that's why I love them.
HS: Well, so much so. And what I thought of envy about England is pub culture. Because after work hours, the streets are filled with people jabbering and talking to each other and it's really quite... I don't know, there's just something very communal about that. I don't know what the equivalent is for us. So ours is a little more isolated, a little more lonely, but you still do get a sense of those connections that can happen in those places.
LA: What does 2025 look like for you as a writer, as a traveler? What have you got in the pipeline?
HS: The traveling for me is never really planned out, but I will most definitely do it. My family is spread out across the country, down in Texas and up in Minnesota and Iowa and North Carolina. I will hit the road at some point in 2025, maybe once or twice for sure. And then in terms of work, I'm working on a show now and I'm halfway into a film that we'll see if it ever gets made, but I write and that's what I keep doing. That's what I get paid for. My career is established.
I'm not super worried about whatever future I have. I can drive across my country, which I grew up in, and feel present and be myself in. It's wonderful, and I have felt that since the documentary. I gained a lot of confidence going across the country. Again, partly a false sense of security because I was with Will and a camera crew, but my confidence level was a lot higher.
And so when I've been back and forth, I've had no hesitancy going into truck stops and bathrooms, and this transition has just been like a get out of jail free card. So I don't know why my euphoria would ever stop. I definitely wake up happier every day. I just feel more present every day. I'm hoping it doesn't stop. I don't know. I have a lot of trans friends who are like, "I don't feel a lot of trans people for you anymore."
I don't know. I think it's a little different for someone who's come out so late. Let me know that it won't stick around forever and you'll just return to being a miserable human being at some point, which I don't know, I never really was. I'm hoping that doesn't happen.
LA: Harper, this was so wonderful. Thank you for giving us so much time. I know we ran over, so I'm very, very, very appreciative.
HS: That's fine. Thank you, guys, and good luck.
LA: Thank you for listening to Women Who Travel. I'm Lale Arikoglu, and you can find me on Instagram @lalehannah. Our engineers are Jake Lummus, James Yost, Vince Fairchild, and Pran Bandi. The show is mixed by Amar Lal at Macrosound. Jude Kampfner of Corporation for Independent Media is our producer. Stephanie Kariuki is our executive producer, and Chris Bannon is Condé Nast's head of Global Audio.
Originally Appeared on Condé Nast Traveler
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