Will Ferrell and Harper Steele have been close friends for decades, since the pair first met on the set of Saturday Night Live, where Steele would eventually become head writer and Ferrell was one of the long-running sketch series’ biggest breakout stars. But when Harper came out as transgender three years ago, it raised the question of whether or not their longtime friendship would suffer any adverse effects.
This question is explored in Will & Harper, a poignant documentary about two friends road-tripping across America, reconnecting with each other and navigating new territory through compassion and kindness. After premiering to rave reviews at the 2024 Sundance Film Festival, Will & Harper is making its way to Netflix this weekend, and we had an opportunity to hear directly from its subjects, along with director Josh Greenbaum, during a recent press conference.
What prompted you to do a cross-country trip and document it with your friend?
WILL: If you know Harper Steele, you know that one of her great loves is taking cross-country road trips. It’s just a great way to get out there and see this country and meet people. And she was lamenting the fact that after her transition that “now I’m wondering if, as a trans woman, if I can still feel safe enough to go into a little out of the way bar or a funky place here and there, or even a rest stop.”
And we started talking about that, and a thought popped into my head. And I made sure she knew I wasn’t trying to exploit our friendship in any way, even though I was trying to get into the lucrative documentary game.
HARPER: Ah ha!
WILL: Cha-ching! But I just said, I have this crazy idea. Please say no, I expect you to say no. But what if we did a road trip and I was able to use it as a way to ask you all these questions I have, even though we’ve known each other for so long. I now have all these questions of what your transition is like and what it means to be trans. And I want to be able to educate myself in the right way. At the same time, we can go to these places and I’ll kind of be your buffer. And we’ll go and talk to people, and maybe it’s a way to kind of kill two birds with one stone. And we’ll film it, and maybe someone will pay for us to take a fun road trip.
HARPER: [laughs]
WILL: And she eventually said yes.
What do you think is the one thing that the two of you were excited about to have audiences see regarding your friendship?
HARPER: I think that because we come from a humor background, I think we wanted to show that life is messy with friendship. And as long as you can keep it funny, you can basically encounter and talk about any subject. As long as you’re kind to each other and making each other laugh. I mean, that’s our kind of relationship.
Josh, humor seems to be a safe space, obviously, for both Will and Harper. And it breaks the potentially uncomfortable silences that could have happened during the course of this documentary. Were there times that you needed to set aside leaning on the comedy to truly understand and learn about Harper’s story? Or did humor create the path to do so?
JOSH: A little bit of both. I think that humor absolutely created the path to start. I think there’s nothing more fun for me than sitting. I was usually in a car right in front of their car, you know, listening with my headset, occasionally checking with them via walkie-talkie or calling them. But listening to their conversations that start usually with a joke and then they organically find their way into one of the conversations. You see many of them in the film.
And, you know, as the journey progressed, I think they just got more and more open and honest with each other, and willing to go to those vulnerable places. And then, of course, toward the end, because this is what they love to do, they would, you know, return back to a great joke. And so, it was really important to me to kind of capture all of it. It would be disingenuous to have a film with these two incredibly funny people that the film itself wasn’t funny. So, that was really important to me.
But at the same time, as you’ll see in the movie, there’s a lot of really hard conversations. And Harper, in particular, is so brave and willing to share her story. She brought along her journals that have some really personal and deep and emotional parts from her past. And I felt like in her opening up to Will, I also got to witness Will, who I’ve known always as a very open person, to become even more so as the journey went on.
WILL: I think it also helps too that Josh, if you know Josh, is very funny. But he’s not as funny as us.
HARPER: Yeah, that helps.
There’s a scene at the Grand Canyon where a woman reveals she was a former therapist, and wasn’t very kind to a patient when they tried to come out to her as trans. What did you learn about yourself in this process, and do you think that it’s reflective of how others outside the LGBTQIA+ community may feel after they see the film?
HARPER: Well, that’s the hope. It’s hard to say if that’s gonna, you know, you can’t control how audiences react. As far as the therapist is concerned, I think that just demonstrates a kind of like evolution of her thinking and the way, you know, her evolution and my evolution were very similar. We came from the same era. I had felt the same thing about myself she was feeling about her patient. So, I think there was a lot of, you know, there needs to be a lot of forgiveness for people in this world who aren’t familiar with trans people and queer people.
At this point, I don’t forgive as much, for younger people especially. We’re in the world. We’ve been here for thousands and thousands of years, so, you know, let’s get over that. But yeah, I’m hoping the audience takes something very positive away from this about trans people, and about friendship and how friendship works.
And on a similar note, what did you learn about America on this trip? This includes Josh.
HARPER: Josh is not as perceptive as Will and I. So, we have to, like —
WILL: Not as funny. Not as perceptive.
HARPER: Yeah.
WILL: That’s fine. We still accept him unconditionally.
JOSH: Doesn’t sound like it. Doesn’t feel like it.
HARPER: Go ahead. What did we learn?
JOSH: I mean, I would say to that point, like there were so many moments where we had any version of expectation on a scene, a place we were about to walk into. I know personally Harper had picked out this bar in the middle of Oklahoma that was the kind of bar that she used to love to go to, and I had to go in beforehand just to sort of say, “Okay,” to my camera team, like, “Why don’t you guys hide over here. Kinda put your cameras here.”
And when I walked in there, I was taken aback. There were Confederate flags. There were political signs that just did not indicate this was going to be a positive experience for Harper, especially because she wanted to go in on her own. And as you see in the film, I think those prejudices and biases that I had were, you know, sort of subverted and not met in a good way. So, you know, a lot of the times I certainly found that we kind of found that adage of “it’s hard to hate up close” to be true. But as you see also in the film, the further you get away from being in a personal space, be it online, that hate, unfortunately, sometimes seems to rear its head again.
WILL: Yeah. I mean, I think what we learned is it’s such a big country, and what I mean by that is that within this country, there is a great capacity for people to, you know, there’s forgiveness out there. There’s people who want to engage. There’s a lot of stuff played up in the media in which we’re made to think we have all these differences when really, there’s a lot more we have in common with each other than we don’t.
That having been said, it’s still not safe for trans people, you know, in certain areas and in certain situations. There still is a lot of hate out there that I was really educated on by going through this journey with Harper. So, there’s definitely a lot to still kinda push through.
At the same time, we ran into some lovely people who were not threatened in any way by Harper. And if anything, were like “fantastic! You do you! And I see you. And come back again. Glad that you came.” You know, they were just super happy that we actually went out of our way to visit their community. And I think overall, that’s our hope that that’s what America is.
JOSH: Harper said something nice the other day that I want to repeat, which you said, you think that people’s resting place is kindness.
HARPER: Yes.
JOSH: And I love that. And I think we all believe that. And I would say we all felt that to a large extent on the trip.
Will & Harper is available to stream exclusively on Netflix.