In Will & Harper, longtime friends and comedic collaborators Will Ferrell and Harper Steele reconnect and embark on a transformative 17-day trek across the United States.
Harper Steele remembers the exact moment fellow comedian Will Ferrell became her friend. It was in the mid 90s, when the pair joined the cast and crew of the famed late-night sketch comedy show Saturday Night Live. Steele was in the writers’ room, largely unsuccessfully pitching sketches, when an idea she had starring Ferrell finally seemed like it would make it to the live broadcast. The sketch, titled “Zipper Boots,” was about a guy who was obsessed with his shoes. It survived the gauntlet of critique all the way to that week’s dress rehearsal before being cut.
“I was sitting there kind of sad, the way you do when you’ve been cut on rewrite day because now that you don’t have a sketch in the show, you don’t have any value,” she recalls. In walked Ferrell with a pair of Florsheim zipper boots for Steele. The gift, which she still owns, was a small gesture that spoke volumes. With one another’s support, the writer and actor thrived: Steele served as an SNL writer for 13 seasons, including four as head writer, and Ferrell went on to star in such beloved films as Anchorman and Old School. When he and writer-director and SNL-alum Adam McKay co-founded the comedy website Funny or Die, Steele joined as creative director.
“Our friendship really came through comedy and how we both were attracted to trying things that were completely off-the-wall,” Ferrell says. “Harper and I connected and I think we supported each other in that way, and that really created a bond.”
Almost 30 years since they first met, that bond takes center stage in the documentary Will & Harper. Following the duo on a nearly three-week cross-country road trip, the film chronicles the latest chapter in their friendship, which involves Steele’s gender transition, adding a layer of complexity and necessary vulnerability between the longtime pals. Against the backdrop of a sociopolitical climate in which laws protecting the human rights of transgender people are actively being banned in state legislatures nationwide, “[the documentary] is an incredibly personal story about two close friends and their open and honest dialogue and journey through change,” says director Josh Greenbaum (Barb and Star Go to Vista Del Mar, Strays, The Short Game).
And because Steele and Ferrell are both very funny people — their professional collaborations also include co-writing Eurovision Song Contest: The Story of Fire Saga — there’s humor alongside emotionally heavy conversations. “Will and Harper’s love language with each other is rooted in comedy and laughter,” Greenbaum continues, “so I wanted to ensure that for every moment of pain, struggle, or discomfort, there were equal moments of levity and laughter.”
Ferrell and Steele spoke with Queue about driving across the country, being an active ally to transgender people, and their enduring friendship.
An edited version of the conversation follows.
Harper Steele and Will Ferrell
Tre’vell Anderson: Harper, an email you sent to family and friends disclosing your transition was the ultimate catalyst for this documentary. What was it like before you hit send?
Harper Steele: Horrific. I had probably thought about sending it every day for three months. So it was really a hard thing to send. And the thing you carry around inside you, it just demonstrates what projected fear can do to you. You really think the ramifications of what you’re about to send are possibly, if not life-threatening, then instantly ruinous.
So it’s just very hard to send that thing. In hindsight, you can laugh at the fact that it’s not ruinous in any way, and it’s the world of entertainment, so literally everyone supported me. But what’s going on in your mind, because you’re dealing with the negative side of this for so long, at least I was, is that sending that letter out is torture.
Will, how did you receive the letter, and how did you come to this idea of doing the documentary and the road trip?
Will Ferrell: It was as surprising a piece of news as I’ve ever received, and because we are comedians, there was a part [of me] like, Wait, is this a joke? In reading the body of the email that Harper sent, it was so thoughtfully laid out that I just knew this was real and this must have been extremely difficult to send. I wrote back right away to say, “Congratulations, and we support you. I support you and this is amazing.” But at the same time, as I’m writing it, I don’t really know what I’m saying because it was such new territory. That subsequently led to us kind of sitting down for the first time [in] a while, and when we were catching up, I was like, “So I’ve got this crazy idea. Please say no immediately, and I’m sure you will, but . . . ”
HS: Yeah, I’ll point out that the first words out of Will’s mouth were, “I’m going to say an idea. I hope it’s not too opportunistic. There’s just a lot of social justice warrior sort of posing [that happens]. I don’t want to use you that way.” He made that very clear, and I’m like, “Okay, well, get on with it. What is it?” Yeah.
And when he says this road trip movie idea, what is your initial response? Was it always a yes?
HS: It was pretty much a quick no. In my mind, I was flattered and I thought, What a cool thing to think about, but I hate being in front of the camera. I mean, more than anything, it’s just something I’m very afraid of. I did feel like, What is the point of it? What could happen?
And I was back in my house in New York for a good three months, and I read a lot of news, especially trans news and things happening in the trans world, and there were so many bills being passed. I was like, I don’t know, maybe there’s some good that can come out of this.
So I pushed myself. And selfishly, I thought, Yeah, this will push me out more too. So I want to be clear that I’m not full of altruism; I also thought that there was something in it for me in terms of just helping me come out.
Harper Steele
A lot of people could have asked me to do this and it wouldn’t have made sense, but it makes sense with Will.
Harper Steele
Will Ferrell
My book We See Each Other: A Black, Trans Journey Through TV & Film documents how visibility for us in the trans community is a paradox. As we in the trans community become more visible, we become more vulnerable in a lot of ways as well. How did that factor into your decision to ultimately thrust yourself into visibility in this way?
HS: If I’m being honest, it’s more unlikely that I will suffer from my visibility than someone else might. That’s just a reality. But I wasn’t thinking about [vulnerability] as much as maybe the privileged side of it. There is a kind of thing with transness going back to Christine Jorgensen, that it’s just always been a white world, and it’s not true. And here I was, going to sort of promote that again.
I had to weigh that with the very wonderful power of Will Ferrell, just the red state, blue state appeal that he has and what that maybe can do. Again, not taking into account the visibility thing, as much maybe as I could have. I would say having Will there, the opportunity, to me, just felt too big. A lot of people could have asked me to do this and it wouldn’t have made sense, but it makes sense with Will.
What do you love about this world of cross-country driving and small-town dive bars, and why did you want to be able to return to these spaces as your true self?
HS: It’s really a drag when you are yourself and you can’t be that everywhere. People feel that in all different forms, not just trans people. But when you are being asked to not be yourself, I think that’s really horrible. I know from the other side of it, just navigating the country for many years, the weirdness I felt doing it as not myself. I say that everything I do now, I haven’t [done] before — even [if I did it] before I transitioned. Everything’s new to me. So why wouldn’t I want to experience that in the state I grew up in, Iowa, and around the kinds of people that I was friends with on some level? Why wouldn’t I want to experience that joy? Why wouldn’t I want them to experience the joy of me, the best me?
And yes, I understand that it’s not safe for everyone. It’s not even safe for me. I went on a road trip with Will Ferrell and a camera crew; I’m not a dummy. But I’ve [driven across the country] a few times by myself and I gained a lot of confidence with the doc that carried over and I discovered many things were fearful projections. It’s not that the whole country’s accepting me now, but I don’t know why they can’t. Everything’s new to me and I want to make the country new to me, too.
Will Ferrell
I don’t know if I realized what it is like to step outside your house, go to the grocery store, and move through the world as a transgender person in a day-to-day way.
Will Ferrell
Harper Steele
Had you, Will, thought about the politics that invariably get thrust on this “issue” or the safety of trans people before filming?
WF: No, I can’t say that I had. I had a more simplistic view: This was a chance for me to ask all the questions that anyone in my position has being around and getting to know someone who’s trans. It was as simple as that. For us to kind of selfishly have a fun road trip, knowing full well we were going to laugh and tell our stories and amuse ourselves, and at the same time, be able to dig down and discuss all these things that I was wondering about . . . As we went on, all the other political ramifications revealed themselves more to me.
The core of the film is just two friends talking with the vulnerability and openness that one has with their really good friend. Did it feel vulnerable to each of you as you were going through it — knowing that there was a camera right there?
WF: It felt vulnerable from the get-go because of that. We might’ve underestimated at first that there were cameras there the whole time, but there is a complete indoctrination period. It’s about day three when you forget that you’re talking in front of a camera. That’s when we probably started really feeling like we could dig into things and explore different topics, ask certain questions.
But at the same time, I was like, Oh, I know I’m going to cry at some point. I said it because I meant it, but I also said it as a way to get over that, almost to push myself to feel safe about potentially doing that. I was trying to give myself permission to feel that vulnerable. And then things kind of happened the way they happened.
HS: I already had experienced the kind of vulnerability that I didn’t know that I had in me just by coming out. That was the most vulnerable moment for me. This next step was a combination of me being more vulnerable, but also allowing my friend in. What do I want to achieve with a person that I love? That’s what the film is about: two friends demonstrating the best possible way to show their love in a crisis.
Harper Steele and Will Ferrell
Will, how has this process changed your understanding of what it means to be a friend, but also to specifically be an ally to your friend who’s also a trans woman?
WF: Obviously it took a lot of courage to send that first email. But I think what I learned is, and Harper expressed this, now I have to walk the walk. I have to live in the community as this person — because I want to and it’s who I am — and be the best ally possible. I don’t know if I realized what it is like to step outside your house, go to the grocery store, and move through the world as a transgender person in a day-to-day way. That was something that I really didn’t take into consideration. I mean, that’s a huge learning moment.
In the film, we talk about how the level of hate that’s out there is something that, until you’re with someone who’s going through it, I don’t know if you are exposed to. I don’t know if it’s something I would’ve ever clocked. And yet, we obviously had some amazing encounters with a lot of people who are completely open — and it just shows that all you need to do is have a conversation and a lot of things get demystified. But boy, there is just a ton of ignorance, a lack of taking the time to think about what anyone in the trans community is going through on a daily level. So that was something for me to take in as well.
Who do you hope watches this film, and what do you want them to take away?
HS: For me, personally, politically, I want it to be a movie about trans people for trans people because honestly, between you and me, Tre’vell, trans people are exceptional and better than cis[gender] people — sorry, Will. But the other thing: I guess I want people to see it outside of a trans story and how friends should navigate difficult periods in their lives because I think that’s part of it too.
WF: I hope it sets an example for people to get out of their comfort zones. It would be amazing if that could happen. Of all the things I’ve gotten to do creatively, it’s one of the things I’m most proud of. And if it helps begin a bunch of little discussions everywhere, then that’s a great start.
