How well do we know our friends? Our neighbors? Ourselves? In the new documentary “Will & Harper,” which opens in select theaters on Sept. 13 and will stream on Netflix starting Sept. 27, the superstar comedian Will Ferrell and his best friend and frequent collaborator, Harper Steele, take a New York-to-California road trip together to try to answer those questions.
Hitting the highway on a quest for meaning is a classic American story, but it hasn’t been told in exactly this fashion before: Steele is a trans woman who came out to her friends, including Ferrell, two years ago. That was after years as a comedy writer, many of them at “Saturday Night Live,” where they both worked and where Steele eventually became a head writer. The two friends explained to me that the show wasn’t always the easiest environment, though they have different reasons for saying so. They also experienced some ups and downs on their cross-country drive, which gave them a chance to talk through what Steele’s transition means for their friendship and to get a clearer sense of how their fellow Americans feel about transgender identity.
As you might expect, the film’s soul-searching often comes wrapped in laughs. But given the politicization of trans rights, even situations the duo set up for silly comedy can turn tense. There’s a key scene in the documentary in which Steele and Ferrell stop for what they hope is a goofy eating challenge at a rowdy Texas steakhouse. It does not wind up being goofy.
That scene, and this emotionally wide-ranging film, evoked feelings in me that work by Will Ferrell hasn’t before. (And I say that as someone who will happily argue for the deeper resonance of his gloriously idiotic “Step Brothers.”) But as “Will & Harper” the movie and Will and Harper the people attest, change can very often be a good and necessary thing — a funny one too.
The hard-hitting first question: How did you become friends? Ferrell: We became friends at “Saturday Night Live.” We were hired in the summer or fall of 1995, and we were all this brand-new group. No one knew each other, and one day Harper and I went to lunch. A very pivotal lunch for me.
Tell me about it. Ferrell: I found out later that a lot of other people were like: “Who’s the tall, maybe sort of handsome guy? He doesn’t seem funny.” Harper and I had lunch and she reported back to the gang, “Hey, that guy, he actually is funny.” I think in some ways that opened the door to people accepting me. Steele: Will, if he’s not on camera — Ferrell: Here it comes. Steele: He’s kind of boring.
I think of comedians as people who like to tease, not the gentlest with displays of vulnerability. Harper, given the internal disconnect you were feeling, what was the “S.N.L.” work environment like for you? Steele: I think if you look in a comedy room, you’re looking at a lot of disassociation and people who are hiding things. We know that because people are drug addicts; Darrell Hammond said that he was cutting himself. You’re walking into that environment, and you don’t want to let a lot of your vulnerability come out. I can’t say I was sitting around there thinking I was a woman. I just know it’s a scary environment. You’re walking in there and as soon as anything got too real, you gotta find a laugh.
Is there anything that you wrote or were in that makes you think, I wouldn’t have handled that subject like that today? Steele: A good third of my comedy. There were a few times even while seeing the sketch mounted, I would go, ugh. I think that is a fear-based thing where you feel like you’ve got to please an audience or you’re losing your job, and you make a decision that is not — I probably felt a lot of fear, impostor syndrome. I might have overstepped bounds. Ferrell: I’d have to go back and review shows, but I’m sure there’d be a fair amount where you’d lament the choice. I mean, in a way, the cast — you’re kind of given this assignment. So I’m going to blame the writers. Steele: Yeah, he’s not culpable at all. [Laughs.] I wrote Monica Lewinsky stuff I wasn’t proud of. I wrote some good Britney Spears stuff and some stuff that I’m not as proud of. I wrote some Clinton things I wasn’t proud of. I’m just moving on. I have to.
The Janet Reno character hits a false note now. Ferrell: That’s something I wouldn’t choose to do now. Steele: This kind of bums me out. I understand the laugh is a drag laugh. It’s, “Hey, look at this guy in a dress, and that’s funny.” It’s absolutely not funny. It’s absolutely a way that we should be able to live in the world. However, with performers and actors, I do like a sense of play. This is an interesting question to me. Do queer people like “The Birdcage,” or do they not? Robin Williams, at least as far as we know, was not a gay man, and yet he spent about half of his comedy career doing a swishy gay guy on camera. Do people think that’s funny, or is it just hurtful? I’ve heard from gay men that it was funny, and I’ve heard from gay men that it was hurtful. I am purple-haired woke, but I wonder if sometimes we take away the joy of playing when we take away some of the range that performers, especially comedy performers, can do.
Harper, you say in the film that you’ve always loved to take cross-country drives. Whose idea was it that Will would go along with you on your first of these drives after transitioning? Steele: It was Will’s idea. I wouldn’t have ever thought of something like that. Nor when he suggested it to me did I think it was a good idea. It took a couple months before I actually thought, Whoa, there might be something here. It wasn’t my first time crossing as Harper. I crossed but I was intensely fearful. I slept in my truck, and I would not go into my favorite kinds of places — the restaurants, the truck stops, the bars. But it was a different thing with Will.
Will, what was your pitch for it? Ferrell: I told her: “I’m not trying to exploit our friendship. Please, I hope you know that. [Laughs.] But this is a crazy enough idea.” By the way, this is the first time we’d seen each other. We were having coffee in my backyard, and we’re both nervous, you know? We’re sitting down and we’re like, “How’s it been going,” just catching up, and that’s when I kind of sprung it on her. Because I’d heard from a mutual friend of ours that she was lamenting the fact that “I don’t know if I can do these road trips the way I used to.” And I said to Harper: “What if we went on a road trip, I went with you, and we film it? I’ll be kind of like your offensive lineman. It’ll be a chance for me to ask all the questions that I have, and we can examine what’s changed, what’s not, but I totally get it if you don’t want to.” I think Harper finally landed on the square that, “Oh, we could help people possibly.” But it didn’t come from a social-justice-warrior place. Steele: We’re both producers and writers, and he’s kind of an actor. Ferrell: I’m either a midlevel A-lister or a top-tier B-list actor. Steele: We make a lot. That’s how we think sometimes: We want to go do something fun. What can we make out of it? That’s part of our process. But I had to talk myself into doing it. I can’t really pin down the motive. There’s a social-justice part of this, because I’m reading the newspaper every day, and more and more trans bills are being offered up, and it’s making me think, Well, you can do something. So I’m thinking about that but then I’m also thinking, Hey, I would like to go across the country with the best bodyguard of all time, who everyone wants to meet and love.
If you had been traveling with someone who wasn’t recognizable, there would have been a lot more anonymity. Was there any tension in that for you? Steele: I didn’t see any of the negative side effects, except for a few places where social media is responding to us, and they wouldn’t respond to me and some other noncelebrity friend of mine. Will is putting a spotlight on this whole thing. So you’ve got people calling me the best possible names that they can come up with in their basements.
There’s a scene in the film that takes place at a steakhouse in Amarillo, Texas. That’s the one you’re referring to, where afterward people were saying nasty things on social media. So that scene happens, and it’s an upsetting experience, and after it in the film, Will, you say you felt as if you let Harper down. Can you unpack that for me? Ferrell: I didn’t really have a grasp on how intense it was going to be and felt responsible for not properly vetting the situation we were putting ourselves in. That felt like it was going to be this benign place where you eat a big steak in the amount of time, and then you walk in and it’s a thousand people seated in this room and I was like, “Oh, why are we here?”
Also, just to paint the picture, you were dressed as Sherlock Holmes. Ferrell: That was a bad choice, too. [Laughs.]
Did people in the restaurant think you were making fun of them somehow? Why were the vibes so off? Ferrell: I mean, the vibes were so off because, to put it bluntly, there was a trans woman sitting — Steele: Next to Sherlock Holmes. To your earlier question, I would say that was a moment where the Will Ferrell factor actually worked against me. Because that was a fishbowl. I was sitting there sort of on display. I’ll say something that wasn’t in the doc. We gave a little toast, and I said something about passing a trans bill, and the room did a kind of reversal and a little bit of a boo and a woman shouted out, “We still love you.” I hate the phrase. I could be misinterpreting this woman completely, but this is the feeling I had in the room: The “still” is conditional. You still love me when I finally give up being trans and give my life over to Christ. They still love me even though I’m some kind of sinner or something. I felt that. Ferrell: I wished I’d walked in and said: “No. This is going to be terrible. Let’s just go.” I was feeling that remorse and guilt of even going there.
Do you have a goal for the movie? Steele: When he asked me to do the project, he was very clear: I don’t want to make an opportunity out of our friendship. On the other end of that, I did want to make an opportunity out of my friendship. I want to be very clear about something, though, that I get in trouble with personally. There’s a process of normalizing queer people for America, and this movie does that. It makes the trans experience more understandable. It’s in a comedy language that they know from Will and me. It’s a good project. It’s representation in a good way. However, to be honest, I’m not that interested in normalizing for people who have hated me for centuries. I want the movie to make other people be gentler and softer and caring, and maybe if you’re a father who loved “Anchorman” and you’ve got a trans kid now, maybe you’re going to open yourself up. Ferrell: You’re willing to sit down and have a conversation. Steele: That’s the work I want the movie to do. But I don’t particularly care about making myself normal to people who don’t like me.
You say toward the end of the film, Harper, that you should have transitioned 40 years ago, but that if you had, none of your life would have happened the same way, which is a profoundly ambivalent emotion. Could you talk through it a little more? Steele: That’s an ever-fluid situation. I land on the side of good fortune of being able to come to this transition when I was 59, but there’s a lot going on there. If I transitioned when I was 20, my life would have been probably different. Maybe wonderful, but probably tough. I don’t think I would have gotten the opportunity to get a comedy job at “Saturday Night Live,” or I would have been looked a little more on as an outlier as a human. But if I had transitioned into an environment like today 40 years ago? Of course. I would have wanted to start my hormonal treatment at 16. When I see young trans people today and how easily they walk through the world — not everywhere, but in the coastal cities or something — there’s a kind of jealousness there. Like, Oh, that would have been wonderful.
How are you feeling now about being out in the world as a woman? Steele: I feel ecstatic. Look, there’s stressors in life: my kids, making money. There are still anxieties. But I basically wake up every morning happy, which is something I didn’t do for, mostly, 59 years. I feel amazing.
You said earlier when we were talking about the Janet Reno sketches that you wonder about whether being woke means we might sometimes take away the range that comedians have. Do you have any sense of how we’re supposed to draw lines between calling out stuff that is harmful and also allowing comedians to play around with subjects? Steele: You dirty bastard. The answer is nope. But yeah, did I defend drag as comedy? I don’t know if I did or didn’t. It was pretty vague, I hope.
I would say ambivalent. Steele: I certainly hope at the very least it was ambivalent. My short answer to that question is always no, I wouldn’t write it again and I don’t think it’s right. I have always thought punching down was wrong. What I have been discovering, like most of us, is that we were punching down sometimes when we didn’t think we were.
Was there any apprehension on your part, Will, about making your personal life into a documentary? You’re not a confessional comedian, and I don’t think of your comedy as you working out your personal stuff. Ferrell: It definitely occurred to me that OK, this will be the audience having more of an insight into who I am, getting to see more of a day-to-day kind of existence. I’ve had a long enough career that I’m very secure in exploring the subject matter with my friend. We’ll see what the reaction is toward me. It’s going to be some positive, some negative or whatever, but I’m at a place where I can take any of it.
Harper, you said you don’t care much about making yourself normal to people. That sounds like an emotionally necessary place to get to but also a hard thing to achieve. How did you get there? Steele: I don’t think I’m quite there. If I walk into what I’m perceiving as a particularly male space I still am self-conscious about who I am and how I’m dressed. When I started this process, I was looking in a lot of forums and the goal was to pass as a woman. But I can’t pass. I’m also not going to change my voice. If I was breaking down my classification I would say I’m a human being and then I am a trans person and then I like to be identified as a trans woman. I think I’m trans first and I feel like that’s the thing that’s been inside me. I just am very happy to be trans. The longer I walk through the world that way, it makes me feel better, or just more myself. When you say “normal,” being trans is normal. You know, I almost wanted to ask you, it’s a question I feel like I need to ask reporters: Do you believe trans people exist? Because quite a few people are skeptical that I exist.
I do believe trans people exist. Steele: OK, thank you very much. It’s just a thing that you go into an interview, you don’t know. Especially the ones asking skeptical questions like: How did you start feeling this way? Or, why do you think you’re a woman? Some of these things can’t be explained to cis people, and they get very frustrated by that.
Can you share the last thing that the other one did that really made you laugh? Steele: You have to imagine, when Will said, “Let’s do this project,” like all of our projects, there is a little bit of us going, like, That’s nuts. That’s the part that both of us love. Ferrell: I think we’re both drawn to holding our hand over the flame for as long as we can. For some people that means controversial. Not to us. It just means how silly can we be and not explain it. My last year on the show, we would have blue notecards of sketch ideas and it’d be like: “Harper, you have to write a sketch called ‘Taco Time.’ Go!” Steele: You’re forgetting a key element that speaks to this perfectly. “Taco Time” is a perfect example, or “Unicorn Mountain.” I would write the first half and then hand it to Will. So I don’t know what he’s gonna do with the sketch. It was always a left turn. Ferrell: David, sorry, just for our benefit, I want to describe to you what “Unicorn Mountain” was about.
Please. Ferrell: “Unicorn Mountain” was a song that led off the sketch and it basically set the premise of being a children’s show. It’s Unicorn Mountain where unicorns live in unity and harmony and they bring joy and they’re magical and they’re fun and let’s all go to Unicorn Mountain. Then we open on myself and Tracy Morgan and — this is Harper’s half — we’re eating a unicorn. We’re talking about how delicious the unicorn was and how easy it was to trap it and kill it because it was so benevolent and sweet and kind and I felt a little bad when we killed it but god this is good unicorn. [Laughs.]
I think I can detect a through line from the answers you just gave to the film you just made. On some level, you’re just trying to make the other guy laugh. Steele: Oh, for sure. Ferrell: Make the other girl or guy laugh.
Yes, I’m sorry. Steele: No worries.
It’s a verbal tic I have that I need to solve. I have two daughters, and I’ll say, “Come over here, guys.” I apologize. Steele: Please don’t worry about that. I say “guys” all the time. “Dudes,” “bros,” those are a little bit more transgressive. But “guys,” I say it to my kids, and they’re all girls. See, look what happened: Two of them are girls. One is a they-them.
It’s a universal experience. Ferrell: Yes. Steele: Yes.
All friendships change over time, I think, and change isn’t always easy. Has anything about your experience challenged or evolved your ideas about friendship? Steele: I think a lot of my friendships, there was an element of fear. The biggest change for me is that I’m not afraid of my friends. That’s pretty huge. That was a big change for me. It brought us closer for sure. Ferrell: For the entire time that we’ve known each other, we never talked as deeply or intensely as we did those 17 days. That’s without a doubt a change. I mean, we’re about to go through an intense period of press, of reflection, of analysis over all this stuff, and at the end maybe Harper might go: “Now I hate you for dragging me through all this. We are no longer friends.” My comedy brain says at the end of this we should announce we’re no longer friends. Steele: I agree. I don’t think it’s a maybe.
This interview has been edited and condensed from two conversations. Listen to and follow “The Interview” on Apple Podcasts, Spotify, YouTube, iHeartRadio, Amazon Music or the New York Times Audio app.
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