Harper Steele opens up about ‘Will & Harper,’ the documentary’s Emmy nominations, friendship with Will Ferrell, and the joy of trans life in this conversation. The documentary is nominated for Outstanding Documentary or Nonfiction Special, Outstanding Directing for a Documentary/Nonfiction Program, Outstanding Cinematography for a Nonfiction Program, Outstanding Picture Editing for a Nonfiction Program, and Outstanding Original Music & Lyrics.
“When you’re traveling across the country with Will Ferrell, it’s just not a trans experience,” Steele says of taking a road trip with Ferrell. “It’s a different thing. In that sense, the movie is not so much as an exploration of red state, blue states, but what friendship or allyship means.”
In this interview with Awards Focus, Harper Steele reflects on the Emmy-nominated documentary ‘Will & Harper,’ which follows her 16-day road trip with longtime friend Will Ferrell. She talks about the freedom and challenges of coming out later in life, the role of humor and writing in processing dysphoria, and the film’s central message of allyship and joy. Steele also shares anecdotes about filming on the road, navigating political tensions, and the surprising impact of watching the documentary with audiences.
When longtime friends Harper Steele and Will Ferrell set out on a 16-day road trip from New York to Los Angeles, they weren’t just retracing familiar highways—they were navigating a new chapter in their three-decade bond. Steele, a former ‘Saturday Night Live’ writer who came out as trans after years of friendship with Ferrell, uses the Emmy-nominated documentary ‘Will & Harper’ to explore identity, allyship, and America itself. Along the way, the pair revisit meaningful places, share plenty of laughs (and Pringles), and open up about what it means to grow together through change.
‘Will & Harper’ is streaming on Netflix.
Awards Focus: It’s so nice to meet you today. How are you doing?
Harper Steele: I’m doing great. How are you?
AF: I’m doing well aside from all these attacks by the federal government on my rights.
Steele: Oh, yeah, it’s our day. I’m writing comedy right now. I’m in the middle of a show. If I pick up the paper or look at anything, it pulls me into a depression and then I’m gone for three hours. I’m avoiding so don’t tell me about the (inaudible) rates.
AF: I have baseball on my TV over MSNBC for the same reason.
Steele: I can’t do it.
AF: ‘Will & Harper’ made the Oscar shortlist, and now it’s received multiple Emmy Awards nominations. How honored are you that the film has been received well by the Television Academy?
Steele: Honored, maybe not as much, but I’m very happy that the film continues to get—for me, all of it, the awards, anything, is just a further chance to promote the movie, get it out there, and keep it out there in the public mind.
AF: When you emailed Will and came out to him, did you have any fear that it would impact your relationship at all?
Steele: Of course, yeah. When you send a coming out letter as late as I did, obviously fear is something that you’ve been living with for a long time. It’s generally projected fear and not real fear, but that’s not something really to fear, but you get very good at projecting that fear.
Yeah, I was terrified that it—Will’s a good person, but it just would color the relationship in a way that I thought would be strange. My own transphobia or something probably carrying around in there.
AF: Yeah. As you traveled across the country with Will over the course of 16 days, did you have any fears about stepping foot in a particular state because of being trans?
Steele: No, no. I’ve driven across three or four different times since, and one time before that trip. I’m a little more wary of certain areas of a town or certain kinds of environments late at night and just sort of depending on the political moment.
But when you’re traveling across the country with Will Ferrell, it’s just not a trans experience. It’s a different thing. In that sense, the movie is not so much as an exploration of red state, blue states, but what friendship or allyship means.
I didn’t—no, I was never really afraid. I think walking into a bar at one point by myself without Will was a very nerve-wracking experience.
AF: I think I’d be more nervous by having all the cameras surrounding me.
Steele: Yeah. You kind of learn to forget the cameras are there very quickly. Our director, who’s done five documentaries, maybe six at this point, said about three days in, you won’t notice the cameras. That was turned out to be kind of the truth, yeah.
AF: What would you say was the most challenging aspect throughout the entire filmmaking process?
Steele: Honestly, there were no challenges for me and Will. We, I think, walked into it thinking, how can we keep talking and entertaining ourselves for 16 days straight?
We got to the beach in Venice and we realized how easy that was for the two of us because we speak the same language, we laugh at the same things, and we were able to keep it going pretty much endlessly, which we can do so it was a lot of fun.
Challenges, I’m sure, for the production side, which I wasn’t as aware of.
AF: Yeah, I’m sure getting, what, 200 hours of footage down to the final 114-minute runtime.
Steele: I had nothing to do with that, thankfully.
AF: Well, if I get a chance to interview Josh, I will be sure to ask him that.
Steele: Yes, yes. It was a process.
AF: You all had a run-in with Indiana’s governor while attending the Pacers game.
Steele: Yeah, not unknowingly. I mean, I wasn’t aware that that was the governor of Indiana. But yeah, I like to say the same thing all the time about situations like that is when Will explained to him what we were doing, he kind of smiled, talked along and didn’t say much, but just kind of looked happy.
I think a lot of people will give up their political beliefs or their ethical stand on something just to get a picture with Will Ferrell. I think that’s almost what was happening there. I think here’s a person who had signed legislation against medical care for trans youth. And yeah, here Will was explaining the purpose of this trip to him, and so there was a bit of a hypocrisy going on there.
I do like to also sort of bracket that with, I don’t necessarily know the man himself and what his true feelings are about; as a politician, he’s acting in ways sometimes that are counter to who he may be, so I don’t want to completely judge a person for being an idiot, and being a politician, which is oftentimes aligned with idiocy.
AF: Personally speaking, I wish there were more films like this when I was growing up because I wouldn’t have repressed myself for so many years. I had that Oh My G-d moment in November 2015.
Steele: Yeah, that’s the point of the film. The point of the film really is for parents and their children to—your hope is that they watch this film together and that’s a conversation that they can have because people of all walks of life like Will Ferrell movies and it’s an entry point that allows, I think, a lot of different people to pick up the conversation about what it means to be trans and also, a very positive film about how joyous and wonderful it can be or is to be trans.
AF: Being a writer myself and coming up through improv, I noticed through the years that a lot of my dysphoria would manufacture itself through the fiction writing. I’m curious if that was the same for you.
Steele: Absolutely. As a writer, you are drawing on yourself and it’s a sing-song way of writing.
Sometimes, you’re trying to let other people know that you’re not queer, and so the writing might take that turn, which would be maybe toxic or male or something, which I’m sure I did.
Other times, you’re trying to let people out in coded language, let people know something about you, which is an entirely different impulse. I did both of them in my writing throughout my entire career.
AF: Yeah. What do you hope people take away from watching the film?
Steele: Well, like I said, I want people to, one, see the positive. I think there’s a kind of a notion that—especially with a parent who’s concerned that your trans child or someone—child can mean anything from very young child to college-age kid or later—is doing something that is very—what’s the word? At one point, probably dangerous and at other points, maybe just sort of—I can see parents thinking it’s ruinous.
I can think there’s all kinds of things you can kind of preconceptions you can have about trans people. What’s not being portrayed quite often is how joyous and exceptional it is to be trans and I joke but I mean it, how much better we are than cis people.
I think the more people can see that, the more they’ll realize all the government legislation and laws being passed probably shouldn’t happen because we need more trans people, happy trans people in the world. What’s better for not just trans people obviously, but better for the world.
AF: When it comes to road trips, what music or audio books do you usually like listening to?
Steele: I have a few podcasts. I love Matt Bernstein when he puts something out. But I mainly listen—it depends what part of the country I’m in. Quite often, if I’m going through the South, I’m a big country music fan and I have a lot of country music that I listen to.
But I’m all over the place. I’ve been collecting records for 40 years, so my musical tastes are fairly broad. But music is a huge part of it. A lot of times music is just being used to keep me awake so I do that.
Podcast-wise, yeah, I have some favorites. My friends, Erin Gibson and Bryan Safi, do one called Issues. Sometimes, I’ll listen to the three dudes who make the, I can’t remember the name of it, Will Arnett and those guys, whatever that podcast is, very popular. Sorry. But yeah, mainly music.
AF: What was it like to go up in a hot air balloon with Forte?
Steele: Neither one of us enjoyed that experience. When we were up there, there was some beauty to it, and it was sort of okay. But I think when I landed, we both knew at that point in our lives we would never go up in a hot air balloon again.
AF: I guess you won’t be competing in the Kentucky Derby Festival Hot Air Balloon Race!
Steele: I will not be doing that. I think a week or two after Will Forte, Will Ferrell, and I were up in that hot air balloon, that same launch area, a balloon went off and I think exploded or crashed and burned or something. I’m done with hot air balloons.
AF: What did you think of the theme song that was written late in the film?
Steele: Shocking. I know Kristen. She’s very talented, but we were giving her all these ridiculous directions. I didn’t really have a concept.
I didn’t see it until maybe the third edit of the film. I didn’t know it was, and to some extent, neither Will nor I knew it was actually happening. It was kind of a bit, and that was it. If it didn’t happen, it would have been fine. But the fact that she came up with that, I’m really excited. I’m glad that was nominated as well.
AF: What’s it been like getting to watch the documentary with audiences at film festivals and other screenings?
Steele: I watched it at Sundance and I watched it in New York. It was just a screening in New York. I didn’t watch it at any other Telluride or any of these places because I don’t particularly love watching myself on camera.
I saw it at Sundance and that was an experience I’ll never forget. It was a standing ovation and quite magical, for someone who’s written a lot of stuff that people hate and people like, but that was not a mixed review. It was a standing ovation so that was unusual.
AF: It was so nice getting to talk this afternoon.
Steele: Thank you, Danielle.