Best Of: Jeremy Strong / Will & Harper's Roadtrip Across America
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From WHYY in Philadelphia, I'm Terry Gross with Fresh Air Weekend. Today, actor Jeremy Strong. He played Kendall Roy on HBO's Succession. He's now starring in The Apprentice as Donald Trump's unscrupulous lawyer and mentor, Roy Cohn. Strong says the film examines the playbook Cohn passed on to Trump. Always attack, deny everything, and never admit defeat.

Also, Will Ferrell and his friend and former SNL writing partner Harper Steele talk about the road trip they took after Harper sent an email explaining she was coming out as a trans woman. In the last 10 years, I've been trying to understand what's going on. Tried to get rid of it over and over again throughout my life. And now I'm giving up the fight. Their road trip is the subject of the new Netflix documentary Will and Harper. That's coming up on Fresh Air Weekend.

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This is Fresh Air Weekend. I'm Terry Gross. Like many fans of HBO's Succession, I became a fan of actor Jeremy Strong through his portrayal of the character Kendall Roy, one of the siblings hoping to take control of their father's media empire while the father was nearing death.

Strong won an Emmy for his performance on Succession and a Tony for his recent starring role on Broadway in Ibsen's An Enemy of the People. Now he's starring in the film The Apprentice. The Apprentice refers to the young Donald Trump as he's trying to establish himself and his father's business as a real estate developer. The person who is mentoring him in how to become successful is Trump's lawyer, the infamous Roy Cohn, played by Jeremy Strong.

Cohn was known for prosecuting and winning the federal government's case against Julius and Ethel Rosenberg on charges of giving nuclear secrets to the Soviets. In a controversial decision, they were sentenced to death and executed in the electric chair in 1953. In 1954, during the communist witch hunt period, Cohn was the chief counsel to Joseph McCarthy's Senate investigations into the communist influence in the U.S.,

Cohn and McCarthy were also leaders in the anti-gay movement that led to an executive order banning gay people from serving in government. But Cohn was a closeted gay man who died of AIDS. He never came out, and he insisted that his disease wasn't AIDS, it was liver cancer. He was disbarred weeks before his death in 1986.

Strong's performance personifies what was written about Cohn on his patch on the AIDS memorial quilt. It read, Bully, Coward, Victim.

Let's start with a scene from early in the film, when Trump and Cohn first meet. Trump has gotten accepted to a private dining club in Manhattan. Cohn is seated at a table with several mobsters, including Fat Tony Salerno, the boss of the Genovese crime family. When Cohn notices Trump, who he's never met, he asks his friend to bring Trump to the table. Cohn is interested in finding out who Trump is. Trump is played by Sebastian Stan. Jeremy Strong as Cohn speaks first.

What is your business, Donald? Real estate. I'm vice president of a Trump organization. Oh, you're Fred Trump's kid? That's right. He's Fred Trump's kid. It sounds like your father is a little tangled up. It looks like he could use a good motor. Tell us about it. Right now, the government and the NAACP are suing us.

They're saying our apartments are segregated. This is America. You can rent to whoever the hell you damn want. But our lawyer wants us to pay a huge fine to settle, and we can't. It's going to bankrupt us and ruin the company. Did you tell the feds to f*** themselves? Sam Street! File a lawsuit. Always file a lawsuit. Fight them in court. Make them prove you're discriminating. Wow. I guess you might have to get us a new lawyer. Of course, it helps if Nixon and the Attorney General are your pals.

Jeremy Strong, welcome to Fresh Air. I love the film and that scene has so much energy to it. You have such swagger in it. Thank you, Terry. I'm honored to be talking to you. Thanks for having me. Oh, it is totally my pleasure. You know, a biopic is different from a film based on an original story. So you had a character who was a known person who you had to portray. What did you do to know, to watch, to listen to him before playing him?

Yeah, you know, I'll just say I haven't watched the film in a while, and hearing that scene back, it's really so charged, isn't it? And Roy, in that scene, encapsulates the playbook, which the film examines the idea that, you know, what Roy Cohn stood for, these principles that he passed on to Donald Trump, always attack, deny everything, and never admit defeat, right?

They're all kind of the DNA of that scene. It contains all of them. It's a great introduction of a character. But your question about playing historical figures, you know, I've done a fair amount of work playing people who, you know, were either alive or were historical figures. John Nicolay in Lincoln, James Reeb in...

in Selma, Jerry Rubin in the Charlie Chicago 7, Lee Harvey Oswald. I feel always an enormous sense of responsibility to a kind of historical veracity and accuracy to try and

capture and render the essence of these people. And ultimately, it's not an intellectual. You're not writing an essay on someone. So the information is sort of emotional, intuitive, visceral information. Did you ever fact check any of it? Like, do you feel a responsibility to not only be have acting truth, but have, you know, like fact truth? Absolutely. Yes, I absolutely feel a sort of fidelity to truth with a capital T, which is funny in this case, because

Roy Cohn, if he's anything, to me, he's like the progenitor of alternative facts. He's like not someone who really espoused truth with a capital T. He thought truth was a play thing that you could...

And I should mention here that the film was written by Gabriel Sherman, who is a journalist who wrote a book about, you know, Murdoch and Fox News. Yeah, a book about Roger Ailes. Yeah, I should have said Ailes, right? Well, no, I mean, it's also about Murdoch. But of course, I read that book when I was working on Succession because...

You know, during that time... Right. Well, that's the thing. Like, I feel like your recent career is so connected to Trump. There's intersectionality there. Yeah. What I want to know is, do you feel very adjacent to Trump? Like, that you know Trump? Because your characters have been so, you know, related to Trump in one way or another and very directly related in The Apprentice. You know, I don't. I don't. If I'm honest...

I feel that my job is to almost be a sort of vessel which involves clearing myself out. But your question about whether I felt adjacent to Trump, I guess I don't. I guess I feel like my job is to...

Be a musician, a first chair musician to play whatever instrument it is that I'm given to play whatever piece of music that I'm given. Because I was going to ask you if you notate your scripts as if they were music, because like in the scene that we just heard, there's real music in your voice. You've got a rhythm. Thank you.

You know, I used to, when I was in college, I sort of have held on to old scripts and plays. And when I did, you know, American Buffalo or something, Look Back in Anger in college, I have a million notes and it's sort of notated and annotated to death. And then at a certain point, I'd stopped writing anything down. I guess at a certain point, you develop a trust that

in your unconscious, intuitive self, that if it's properly absorbed something, then it will be there somehow. Now, I think voice is very important to me for any character, and Roy had a very, very particular voice

way of speaking and a very specific pentameter and the music of that is something that becomes your job to both master and then throw away. You know, he writes in Hamlet, Shakespeare says that use can almost change the stamp of nature and I feel that actors, especially when you're attempting to do some kind of transformational work, which is the kind of work that I love the most and have been inspired by in my life the most,

your job is to kind of change the stamp of your nature. And voice is a really key part of that because there's something about a person's voice that is like their eyes. It's such a way in to that person.

My guest is Jeremy Strong. He played Kendall Roy in HBO's Succession. He stars in the new film The Apprentice as the young Donald Trump's unethical lawyer and mentor, Roy Cohn. We'll hear more of our conversation after a break. I'm Terry Gross, and this is Fresh Air Weekend.

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This is Fresh Air Weekend. I'm Terry Gross. Let's get back to my interview with Jeremy Strong. He became famous for his role on HBO's Succession as Kendall Roy. He stars on the new film The Apprentice. It's about Donald Trump as a young man striving to become successful and his unethical lawyer and mentor, Roy Cohn, played by Jeremy Strong.

Let's talk about Succession a little bit. Sure. I don't know if I'll remember anything, Terry, but let's try. Okay, great. Thank you. So Succession is the HBO series about a media mogul who owns a Fox News kind of conservative cable network. He owns theme parks and cruise ships. He's old, his health is fragile, and his four adult children are competing to see which of them will take their father's place.

So you auditioned initially for Roman, the Kieran Culkin character, and then Adam McKay, who was an executive producer of Succession, after you didn't get the part of Roman, he asked you to audition for Kendall, which is the role you became famous for. And, you know, Kendall is this mix of, like, confidence, sometimes overconfidence, right?

And insecurity, uncertainty, indecisiveness, sometimes decisiveness, but the decision is frequently not the right one. So there's this constant conflict going on within him. What did you relate to about that brew of contradictions within him? You know, my experience as an actor was an experience of years and years and years of kind of struggling and feeling thwarted.

and feeling a sense of being denied, a sense of being in a wilderness. So those feelings were accessible to me, the way that Kendall, you know, who begins the series as the incumbent and then is sort of, you know, held down and subverted and thwarted,

but with a great need and desire to do the thing he feels that he is born to do. That's something, that vector, it was very alive for me.

So in one of the final scenes in Succession, the father has died. The children are fighting to keep the company while the head of another company is trying to buy it out. Kendall has pitched himself as the successor at the final board meeting before the decision is made. They're about to vote and each of the three siblings has a vote too. And the decisive vote is going to be the sister, Shiv's.

And before she says what her vote is going to be, she calls a meeting in another room with you and Kieran Culkin's character. And she explains why she's not going to vote for you. And this refers back to

When you confessed to your siblings that you had accidentally killed a young man while you were very high and he had a drug contact and you were too high to be driving and you accidentally drove off the road into a lake and you couldn't rescue him from the car. So what you did was like run away and then like pretend like you had nothing to do with it. But you confessed to your father.

who covered it up for you, and then you were indebted to him. So I want to play that scene where the three siblings are in a separate room, and Shiv, your character's sister, is explaining why she's not going to vote for you. I feel like if I don't get to do this, I feel like that's it. Like I might die. Shiv, can we go in that room? Can you just vote? Please. Please.

You can't be CEO. You can't, because you killed someone. Wh-wh-which? What? Wait, what do you mean? Which? What, like, you killed so many people you forgot which one? That's not an issue.

That didn't happen. Wait, it didn't? As in what? It's just a thing I said. It's a thing I said. I made it up. You made it up? It was a difficult time for us, and I think I, you know, must have something from nothing because I wanted for us all to bond at a difficult moment. Wait, it was a move? No, not, there was a kid. There was that kid. So there was a kid? I had like a toke and a beer and not, I didn't even get in the car. Hold on, what?

I felt bad and I false-memoried it. Like, I'm totally clean. I can do this. Wait. Did it happen or did it not happen? It did not happen. It did not happen. I wasn't even there. It did not happen. Dude. Vote for me. Just please, vote for me. Shiv, vote for me. No. Yes. No. Shiv, don't do this. You can't do this. No. Absolutely not, man. Absolutely not. No. Why? Why?

No, why? What, just... I love you. I really, I love you, but I can't on f***ing stomach you. This is disgusting. It doesn't even make any sense. I'm the eldest boy! I am the eldest boy! And, you know, it mattered to him. He wanted this to go on.

Such a great scene. And I should mention that Sarah Snook playing Shiv and Kieran Culkin playing Roman. What was that day like for you? That's such an intense scene. And it ends up where you're actually kind of strangling Kieran Culkin's character. So what is a day like that?

How does that play out for you? It's such an emotional scene. I mean, your character has said he's going to die if he doesn't get to be CEO. And I think he means it. I mean, I think his life is invested in taking over from his father. He always, always, since childhood, believed he would do that. I haven't watched that or listened to it in a really long time. It's really...

affects me like I can feel it in my chest and in my body right now how does it affect you like what are you feeling in addition to pain probably just pain um you know it was a kind of volcanic day right and the stakes were so high both for me as an actor and for Kendall in his life

So of course you approach a day like that with a certain amount of, or I do, dread and trepidation of just like, will it come? Will we clear the bar of what this writing demands and what the potential for this is? Which is really a kind of cataclysmic scene.

So I want to end with a song. There are two musical moments in Succession that really stand out. One was when you were practicing, you're kind of doing a soundcheck for your birthday party that you've planned, and it's a very elaborate, really ridiculous party that you've planned that doesn't work out well. But you're rehearsing or doing the soundcheck with the Billy Joel song, Honesty. And the song I want to end with is...

L to the OG. Right, which my kids can now do a pretty good version of. Good. So if I listen to it any more times, so will I be able to. Okay, so this is like the rap that you do at your father's 50th anniversary of his business. Yeah. The way you say L to the OG, the way your voice raises on the OG, it's like a question mark for

Usually in hip-hop, there's a lot of assertion and almost arrogance, like, this is who I am. Sure. So was that a choice to make it sound a little tentative and insecure, like a question as opposed to an exclamation? No, it's interesting. Back when I would go to some acting classes, people would always say, oh, I like the choice you made, or that's an interesting choice. I never, ever experienced anything as a choice.

I experience it as an impulse and I've learned to trust those impulses. So that's just when I was trying out things in the car, trying to learn that rap in the back of a sedan on my way on some road in Scotland, that's just ended up feeling like the best way to sing it. And so I just stuck with it because, you know...

Necessity is the mother of invention and I had like two days to be able to stand up there and do it. And I didn't want anyone to hear it until the first take. So one thing I love about that scene is the look on Kieran and Sarah and everybody's faces, which is just like incredible.

It was like horror. But that's because they'd never seen me do it until then. Oh, so that was a real reaction in part? Yeah, but that's the thing about film. You want it to be real, or at least I do. That's really funny. So one more question and then I will let you go because I've kept you a long time. How did it feel to end your relationship with Kendall when the series ended? Did you feel liberated from him or did you miss him?

To be honest, I've sort of just put it away. Like I put away all of these things. You know, I have a stack of scripts in my office and it's like this stack of lives that I've had that when they're over, they're over. And you just put them away. And I put it away because, you know, I have a life and children and then I moved on to the Ibsen play and that took up all of me.

So, you know, I don't feel more of a kinship with that role than I do with any other role that I've ever played, which might sound like a strange thing because I know it's the thing that I've become known most for. You know, one day maybe I'll watch it all back and sort of take in the magnitude of what it was. But I've probably had to protect myself from that because I don't think that that would...

serve me uh if that makes any sense you know it's the it's the Rudyard Kipling thing of like you have to treat success and and failure as imposters I find that you do your work you give it everything and then that's it like that's all you need to be involved with

So whether it becomes the biggest thing in the world, whether something wins the Academy Award, that's not your concern. Your concern is to be all in when you're doing it.

Well, it's just been great to talk with you. I admire your work so much. Thank you so much for being on our show. Yeah, it's so great to talk to you. And let's end with L to the OG. Okay. So this is Jeremy Strong, who stars as Roy Cohn in the new movie The Apprentice. And here's L to the OG, which he sings in succession. Thank you again. Thanks, Terry. L to the OG. Dude be the OG. A and he playin'.

Playing like a pro, C, L to the O, G, Dude be the OG, A, and he playing...

Playing like a pro, make some noise. A1 ratings, ADK wine. Never gonna stop, baby, for the time, bro. Don't get it twisted, I've been through hell. But since I said that, I'm alive and well. Shaper of views, creator of news. Father of many, paid all his dues. So don't try to run your mouth at the king. Just pucker up and go kiss the ring. L to the OG.

When Will Ferrell found out that his close friend and former Saturday Night Live writing partner was coming out as a trans woman named Harper Steele, Ferrell decided to make a documentary about this transitional period in their friendship.

Early in the film, Will and Harper read the coming out letter Harper sent to Will in 2021 when Harper was 59. Will reads first. Hey, Will, something I need you to know. I'm old now, and as ridiculous and unnecessary as it may seem to report, I'll be transitioning to live as a woman. In the last 10 years, I've been trying to understand what's going on. Tried to get rid of it over and over again throughout my life.

and now I'm giving up the fight. When I was young, I thought all boys felt like me. Then I thought, maybe I'm just a weirdo. Then I pushed it away for many years and ended up in therapy. It's a wonderful thing when your mind and body revolt against the unnatural, despondent thing you become. I doubt being a trans woman will change my personality that much. Instead of an asshole, I'll be a bitch. I think it's made me a lot happier.

I'd like to say my happiness translates to a bright, carefree future full of courage and confidence, but no such luck. I carry self-doubt and fear around me like the comedian I've been my whole life.

As their friendship journeys into new territory, the film follows Will and Harper on a cross-country road trip from New York to California, alternating driving. They stop on places that Harper used to go to before transitioning that she's now afraid may be unsafe for her to go alone as a trans woman, like a dive bar in Oklahoma, an Indiana Pacers basketball game, and a steakhouse in Texas.

Their new film, Will and Harper, is streaming on Netflix. The two met in 1995 when they both started working at Saturday Night Live. Harper stayed until 2008 and spent the final four years as head writer. After that, she moved to the comedy website and production company Funny or Die, which was founded by Will Ferrell and Adam McKay.

Farrell left SNL in 2002. He starred in such films as Anchorman, Talladega Nights, and Blades of Glory. He was an executive producer of HBO's Succession.

Will Ferrell, Harper Steele, welcome to Fresh Air. I really like the movie, and I feel like I got to know you, Harper, in the film. So I'm glad you shared your story, and I'm glad, Will, that you shared your friendship together. So, Harper, what made you think it was the right time to come out to Friends?

Well, it wasn't a decision about right timing. It was a decision about living in misery and not wanting to do that anymore. So it just took me a long time to finally give up. And I do think of it as a giving up. I just collapsed into myself and found the other side. And it's been so much better. Right.

Well, what was your reaction when you got that letter? And I'm even wondering, and excuse me if this sounds weird, I'm even wondering if you thought it was a joke at first, you know, if you were that unprepared. Right. Because Harper is a comedy writer. No, definitely unprepared. It was a complete surprise knowing Harper for as long as I did knowing her dead self and

That was an expertly acted role for all those years because it was so convincing that I didn't see it coming.

And then you fall back on, whoa, what do I do? What's the right thing to say? How should I say it? And I just wanted to respond quickly and say, oh, my God, this is wonderful. Wow, congrats. And I can't wait to see you in person, which took a little while. You know, you mentioned that you felt Harper had been playing a role. And I was wondering, you know, Harper, in your years on Saturday Night Live,

All the actors were playing roles. They were all in, like, sketch comedy, playing a different role each week or doing their own recurring characters. Did you feel in those years that you were playing a role, too, but you weren't on stage? You were playing your role in real life. Yeah, I mean, I always felt that way. I don't like to turn these things into black and white. Harper Steele has been with me since I was born, so...

I was at SNL as myself, Harper Steele. And yes, there's a protective armor around that that was the role that I played. And I don't even hate the role. It just was just sort of probably my survival instincts, unconscious maybe even.

Will, when you were first getting to know your old friend as Harper, did you worry that you would, like, use the wrong language or accidentally misgender her because you were so used to your friend having a different name and a different gender publicly? Yes. The public-facing version. Yes. I mean, that was all...

part of the learning curve. Uh, and, and I'm sure when we sat down in our, in my backyard to have a cup of coffee, I probably misgendered you accidentally in that, that hour and a half that we sat down and Harper was, you know, just made it really clear that like, don't worry about it. Like, you know, like I'm glad that you're recognizing it and, and, and correct the moment as, as well as you can, but it's, it's going to take some time. And, uh,

To, you know, be cognizant of it, but at the same time, don't be too hard on yourself. And that my heart's in the right place with all of it. You know, after spending time, after really getting to be around Harper, that becomes very easy. I mean, it becomes very easy to...

use the right pronouns. I think, Harper, right, everyone in your life has gone through this kind of... I've gone through it. Yeah. I've gone through it. I mean, you know, I think as a stock phrase I used, I'm not the kind of guy who does that. That stock phrase is automatic. And so, yeah, I misgender myself. And when it comes to friends, I sort of feel out the situation if people are misgendering me

and it's annoying me, then I correct them. If it's friends, I correct them in my funny way. But I don't like my friends to feel on edge around me talking about my transition or talking about who I am now. I don't want them to feel that, so I'm not interested in nailing everyone around me. What's happened with me, though, as I've become more comfortable with it and it's become second nature, I've found...

I found a certain vigilance when we're out together and someone by chance does Miss Gender Harper. I'm like, uh-uh, uh-uh, excuse me. No, I've got a good ally here now. She, her, okay? Oh, yeah, yeah, sorry, sorry, sorry. So I find myself, I'm like almost, I almost get now irritable with it.

My guests are Will Ferrell and Harper Steele. Their new documentary called Will and Harper is streaming on Netflix. We'll hear more of our conversation after a break. This is Fresh Air Weekend. This message comes from NPR sponsor Oracle Cloud Infrastructure. AI may be the most important new computer technology ever, but AI needs a lot of processing speed, and that gets expensive fast.

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This is Fresh Air Weekend. I'm Terry Gross. Let's get back to my interview with Will Ferrell and Harper Steele. They first met in 1995, when Will became a cast member of Saturday Night Live and Harper became a writer on the show. They collaborated on sketches and became close friends. Their new Netflix documentary, Will and Harper, is about their road trip together after Harper came out as a trans woman in 2021.

In the film, you both go to some places that you'd feel comfortable in Harper before your transition, but you were kind of afraid to go to by yourself after transition. And part of the concept of the movie is that you're going to do this road trip together and together you will go to those uncomfortable places. So you get a sense of, can I be here without being targeted or humiliated and just be myself?

And it seems like, you know, judging from the movie that the places you used to go to before transitioning were really the kind of like, you know, bro or really like, you know, masculine, you know, like hyper male kind of places like, you know, dive bars and stock car races, truck stops. What attracted you to those kinds of places before transitioning? Yeah.

Well, they're beautiful places, wonderful places where all kinds of humanity, all kinds of Americans exist. And I love them now as much as I did then. I mean, yeah, I grew up in the Midwest. These are homes to me. These are my people.

So what's it like going to those places, recognizably as a woman? You're out. Well, it's always a little bit more fraught. And I don't know if it's because I'm a woman or if it's because I'm a trans woman. I can't quite discern that at this point. And I know when going to a car dealership, it's because I'm a woman. Yeah.

They don't talk to me the same way. They don't think I know anything about cars. But no, I'm joking. Maybe you're not. Yeah, no, I'm not joking about that. That's a real thing. But no, this all gets a little muddy for me because one, everyone should know that when you cross the country with a camera crew and Will Ferrell, this is not a normal trans experience. And on top of it, I have a lot of

privilege. And I have the ability to get in a car and get the heck out of places. So it's not a normal trans experience that I experienced. Now, I did go back and forth across the country twice since the film because I do that and I like that. And I have, yeah, I have more confidence walking into these places. Now, certain places, and I assume you know this, Terry,

being a woman, are not fun to go in at 11 o'clock in the morning

at night, you know, alone as a woman. So I probably am more cautious now for sure. You mentioned that you were in a unique situation traveling with Will Ferrell, a very recognizable star of stage and screen. Thank you. I appreciate the stage. Yes. He's over there floating on air now. I love it. But, you know, it's not only that you were there with Will Ferrell, it's also that there was a camera crew there with you.

Yeah.

Well, because the film is not really about a trans woman crossing the country by herself. It's about two friends and how they're navigating a friendship. So I was just looking at...

This will be an interesting way to have a conversation about this subject with someone that I care about. It was also a look inside to the way we like to entertain each other and the way we would have done a road trip even without cameras. I would have brought my Sherlock Holmes costume to get my friend to laugh as a callback to things we've done in the past. So it was also representative of that.

One of the places you go, I mean, the place you go into in the movie with the Sherlock Holmes costume is a steakhouse in Texas. And if I understand correctly, you get this like, you see the plate of steak on camera. The steak is kind of overlapping the plate. It's so big. Yes, 72 ounces of steak. Yeah, and you have like 60 minutes to eat it. And then they come and take away the plate?

Mm-hmm. Well, there's some fine print in there. You have to eat the steak and a baked potato and two little weird fried shrimps and I think some broccoli. So it's not just the steak. You've got to eat down all of that in 60 minutes.

And anyway, I don't know why anybody would want to do that. But I agree. You go there in the Sherlock Holmes, you know, with Will in the Sherlock Holmes costume and things don't go well. Harper, would you describe what happened and your reaction to it? Well, this was a negative reaction.

consequences of traveling around the country with Will Ferrell because the room sort of crowded in on us. A lot of photographs, a lot of cameras right in our faces, mainly Will's face. And I started to feel a little bit judged in the room. It's a feeling if you're trans. When people are

Looking at you, and again, I don't know if everyone in that room was judging me the way that I felt. They might have been saying, I'm happy to see a trans person here in Amarillo. I can't say that for sure, but later we do see a lot of tweets. Is that what they're still called? I don't know what they're called. Xs. Xs. We see a lot of Xs that people wrote about the experience. And yeah, what I felt was what was there.

And, Will, you felt really guilty afterwards because it was an unpleasant experience for Harper and you actually teared up. Yeah, I felt kind of ashamed a little bit. This was just supposed to be a silly stop along our way and another piece of Americana. And I just carried a little bit of the guilt and the burden of like, why did we even go in there?

There was no need to. And I subjected my friend to, you know, this ridicule and scorn that was, we just didn't need to go there. And yet I think it's a powerful part of the film. So in hindsight, it turned out to be kind of valuable for me to feel that and to see that that kind of hate does exist out there, you know, for the trans community.

So at one point you go to a dirt track race, a kind of car race. And on the way out, Harper, you say, I'm not afraid of these people. I'm afraid of hating myself. And then you tear up in the car as you're talking to Will. And Will, I think if I'm remembering correctly, what you do is, you know, kind of try to

To let Harper know that you understand and to try to comfort her. So like you rub her shoulder as you sit next to each other in the car. And I was thinking, and this might be a strange question, and I hope it's not an inappropriate one, but I think it's often really awkward when a man and a woman, when one tries to comfort the other, when they're good friends and there's nothing sexual about the relationship. How do you know?

Well, I said it's an uncomfortable, weird question, but yes, exactly. There isn't, by the way. But when there is nothing sexual and you don't want to have the other person misinterpret it, even though you might want to hug them to console them, you may be uncomfortable doing it. And I'm wondering, you know, you each get a chance to tear up in the movie, and I'm wondering if you were kind of self-conscious about how can I physically...

comfort the other person without either of us feeling uncomfortable or giving the wrong impression or

Well, I think with any human, that's a navigation. You know, friends. I'm not talking about random hugging. I'm talking about friends. But Will has pointed out many times that before I transitioned, hugging was not in the equation. I would purposely... Will would hug me knowing that I would go stiff as a board and just hate it. And now I'm a hugger. So I...

I will accept all hugs from good friends. Between men and women, between, you know, anyone, there's a camaraderie hug that can happen, and that's what I felt. I felt that arm on my shoulder, I'm sure, and I felt it has meaning. It's touch. It's I care about you. And that's, you know, that's wonderful. Yeah, and I don't know if this answers your question, Terry, but in that moment...

I'm navigating it as well and trying, yeah, trying to comfort my friend at the same time. If I had reached over, and I'm not saying you're suggesting this, but...

If I'd reached over and given her a bear hug and said, it's going to be okay. Like that, that would have been fantastic. Well, I guess it would have. And so I'm like, no, I need to let my friend feel this. I need to just be there and, and, and not say a word. It wasn't my place. And I think that pat on the shoulder is just like,

wow, buddy, we just experienced something here. And it was powerful. Harper, when you decided that you were just going to do it and transition, what kind of woman did you want to be, just in terms of how you wanted to look? And, you know, there's such a broad range of what it is to be a woman. You know, there's women who are very kind of

what would be described as feminine and women who are very what would be described as masculine. And it's a huge scale of visual styles, of voices, of ways of being in the world. That's a very strange question to me because I came out as me. I don't know what that means in terms of what it means to be a certain kind of woman. I am a woman. I came out

I acknowledge that. Again, it overpowered me the way it was supposed to because nature wins. And I am female. I look at fashion and I look at clothing and I go, wow, I want that or I want that. But I don't look at types of women and say I want to be that type of woman. I mean, we all like cool people. But no, that never entered my mind. In fact, the question to me is a little –

It's not a dated question. I'm not accusing you of that. The question to me is just so foreign to me because I didn't have like a mapping of femininity for me. I just was feeling who I am and I'm still that person.

I'm sorry if the question was offensive, but I'm kind of glad I asked it because your answer was so good. And I think it's a very informative answer. I hope I didn't make it sound like it was an offensive question. It's just I'm sure other trans people might want to answer that differently. And we are not a monolith for sure. But that's how I answered it.

You also say, Harper, that the more makeup you wear, the worse you feel about your face. And you say the, quote, prettier I get, the more I see my flaws. It's making me self-aware of my very masculine face. Yeah. So where has that left you in terms of, you know, wearing makeup or not? And how much do you want to care about your face? No, I love makeup. I'm just not.

perfect at it. And again, what human is not fluid in the way that they see themselves? What human is not like always maybe working on to look better, to lose weight, to feel better about their bodies and feel better about themselves? I'm on a similar trajectory. Transitioning does...

make it a little more, I don't know, hyper aware of how you're wanting to look and how you want to be in the world. But yeah, I mean, dysphoria is real. I was unfortunately born, you know, was assigned male at birth. And so

Yeah, I've had to deal with that. But it's true. But you don't know how many women have walked up to me and said, oh, yeah, that's exactly how I feel. You know what I think? I think that the whole body positivity movement

has not acknowledged faces. Faces are totally not about body positivity. People have plastic surgery. You have to undergo the knife to feel like you have an acceptable face. Aging is not something you're supposed to show on your face. Wrinkles are taboo. If you can afford it, that's what people do. And I wonder if you have any thoughts about that, about body positivity not being

especially aging faces. Hollywood and the business that I work in, we value faces. Somehow Will Ferrell slipped through. Somehow. Somehow. But I'm going to get some work done after this. Okay, good, good. I just made up my mind. I just made up my mind right now.

We value faces. And so I like the middle of the country because it's me. There's people out there, like real people. Will, do you have any thoughts about that as you get older? Well, men are lucky in that, you know. You can be ugly. We can be ugly. We can be ugly. And we can look distinguished all of a sudden. Yeah, that's true. But no, I, you know.

It's funny. I'm in comedy, so it's not critical for me to worry about that. But it's not my nature anyway. And in fact, I remember giving, doing a Q&A somewhere, and one of the questions from the audience was, why are your eyebrows so white? I said, because I have gray hair. It's called the aging process.

Will, how do you think you were changed by the experience of this road trip? You know, you get an email from a friend announcing this kind of dramatic news, and I didn't really stop to think how much pain, how much anguish there was to get to that point, how much thought it took to write that email. And yeah, just Harper and I going around, visiting her sister in Iowa, and

You know, the part where she's looking through photographs and uncovering this story that this was something that obviously was a part of her this whole time. And the sadness of her kind of putting it aside, kind of squashing it down. But then the courage that it took to get to that point where she was like, enough, I'm not going to, I'm going to give up the fight and leave.

Yeah, I just learned how incredibly strong she is, how articulate she is. She's always made me laugh, and I knew she's a smart person, but not that smart. No way. But we have these conversations. It's on tape now. Yeah, it's on tape. It's on tape. And a lot of people have come up to us just saying, it's just nice to see friends stick up for each other. I think that's what we're most proud of about this whole thing. Yeah.

And making Will laugh. If I can make Will laugh, then job well done. It's been great to talk to you both. Congratulations on the movie, and thank you so much. Oh, thank you. Thanks, sir. Thank you. Will Ferrell and Harper Steele's new movie, Will and Harper, about their road trip together and their friendship, is streaming on Netflix. ♪

Fresh Air Weekend is produced by Teresa Madden. Fresh Air's executive producer is Danny Miller. Our technical director is Audrey Bentham. Our engineer is Adam Staniszewski. Our co-host is Tanya Mosley. I'm Terry Gross. This message comes from NPR sponsor Merrill. Whatever your financial goals are, you want a straightforward path there. But the real world doesn't usually work that way. Merrill understands that.

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