@Courtesy of Netflix

Q: How did you get involved in this project?  

Josh Greenbaum: I actually knew them prior to making this project, which is the first time I’ve ever made a documentary where I knew my subjects beforehand. I’ve known Will for about eight or so years. He produced my first movie titled Barb and Star Go to Vista Del Mar. He starred in my next movie Strays. We’ve been friends for awhile, and now I’ve known Harper for about three or four years. I was introduced to her through Kristen Wiig while I was making Barb and Star. And then I was brought into the mix of this incredible story, in this incredible film through our producers Rafael Marmor and Jessica Elbaum, who happened to be Will’s business partner.

Q: What prompted you to travel across the Country and document it with your friend? Why did you all decide to do it in the winter time? 

Will Ferrell: We actually did it in March, so we were right on the real cold.  If you know Harper Steele, you know that  one of her great loves is taking cross country road trips. She’s done it as long as I’ve known her, she spent her college years doing it. It’s one of the things that she loves about this country, that you can take these amazing trips, get out there, see this country, meet people.  After the transition she was wondering if as a trans woman she could still feel safe enough to go into some of these, a little out of the way bars, or a funky place here and there, or even a rest stop. 

We started talking about that and it just popped into my head and we made it. I made sure she knew I wasn’t trying to exploit our friendship in any way, trying to get into the lucrative documentary game. I just said: “I have this crazy idea. Please say no. What if we did a road trip? We were able to use it as a way to ask each other all these questions. We’ve known each other for so long, I had all these questions about  what her transition was like, what it means to be trans. At the same time, I wanted to be able to educate myself in the right way. We could go to these places and I would be her buffer. We’d go and talk to people, maybe it would be a way to kill two birds with one stone And maybe someone will pay for us to take a fun road trip. She eventually said yes.  

Q: What do you think is about your friendship with Will that kept you guys bonded all these years? 

Harper Steele: Comedy is where we center our life around. I would say that’s the basis of our friendship. It’s been that way since the day we met. But I want to go back to something now: If I had done this in the summer, I would have the best legs. It was so disappointing that they said let’s do this in the cold weather…

Q: What is the one thing that the two of you were excited about to have audiences seeing your friendship?  

Harper Steele: Because we come from a humor background, we wanted to show that life is messy with friendship. As long as you can keep it funny, you can basically talk about any subject. That’s our kind of relationship, that is what we wanted to get across.  

Q: What advice would you give to parents as they navigate the challenges of helping their children become who they really are? 

Harper Steele: Personally, I would tell them to vote for the people that are gonna support that. We need to keep in mind that politics does have a certain amount of control over the laws. I would say to any parent, you’re very fortunate to have trans children. Get out of the way, let them be themselves. They’ll be taking over the world soon enough.  

Will Ferrell: Just listen and not try to be too perfect about your engagement with your kids.

@Courtesy of Netflix

Q: Were there times that you needed to lean on the comedy to truly understand and learn about the Harper story? Or did the humor create the path? 

Josh Greenbaum: A little bit of both. The humor absolutely created the path to start. There was nothing more fun for me than sitting in the car right in front of theirs, listening with my headset to their conversations that usually started with a joke, then they organically find their way into one of the conversations you see in the film. As the journey progressed they just got more and more open and honest with each other, willing to go to vulnerable places.

And then of course, towards the end, because that’s what they love to do, they would turn back to a great joke. It was really important to me to capture all of it. It would have been disingenuous to have a film with these two incredibly funny people and the film itself wasn’t funny. In the movie there’s a lot of really hard conversations. Harper in particular is so brave and willing to share her story. She brought along her journals that have some really personal, deep and emotional parts from her past. 

Will Ferrell: I think it also helps that Josh is very funny. But he’s not as funny as us. That helps. Yeah. None of us felt like we had to compete. 

Q: Can you talk about the musical choices for the film? Did any of them have any special meanings for you? Can you also talk about this theme song by Kristen Wiig?

Josh Greenbaum: She just stopped picking up their calls at home. That was kind of hilarious. Music music is everything to me as a director, it’s the fastest way to understand tone in a film. It’s emotion, it’s pace, it’s everything. And of course, what would be a road trip without great music? 

Harper Steele: I have a collection of 10,000 records. But I stayed out of the music, even if I had great suggestions. I brought along a record player, I used to do that on all my road trips.  When I’m on the road, I like country music. After one of our first conversations, I sent over a bunch of tracks that were fantastic. Many of which are in the film. 

Josh Greenbaum: The one that I quickly flagged was a song called Go With Me by Gene and Debbie, that I had never heard before. I thought it could have been our last song and that’s where it is. 

Harper Steele: So happy that that song finally got there. 

Will Ferrell: We thought it’d be a funny runner, even if Kristen never got to make a song like that. Low and behold. We had a final screening amongst ourselves because Josh said: “ Can you guys come watch the movie again? I made some small changes” and he surprised us with her song at the end credits. It was another special moment of joy for us. 

Q: What did you learn about America in the process of this trip? 

Josh Greenbaum:  Harper had picked out this bar in the middle of Oklahoma, that kind of bar that she used to love to go to. I had to go in beforehand just to put the cameras in. 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, those prejudices and biases that I had were subverted. We found that it’s hard to hate up close. But as you see also in the film, the further you get away from being in a personal space, online that hate, unfortunately, sometimes seems to raise its head again.  

Will Ferrell: We learned that It’s such a big country. There is forgiveness out there people 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 there’s a lot more we have in common with each other. On the other hand it’s still not safe for trans people in certain areas and certain situations, there still is a lot of hate out there. I was really educated by going through this journey with Harper. We ran into some lovely people who were not threatened in any way by Harper. They were just super happy that we actually went on our way to visit their community. Overall that’s our hope that that’s what America is. 

Josh Greenbaum: Harper said something nice the other day that I want to repeat: people’s resting place is kindness. I love that. I would say we all felt that to a large extent on the trip. 

Harper Steele: My goal after the transition was to see if the Country still loves me or if I still love the Country. And I still love my Country.  

@Courtesy of Netflix

Q: What were you most nervous about going into this journey? 

Harper Steele: I was hesitant at first to do it. I had to think about that. I don’t like being on camera, I knew I was opening myself up to a lot of vulnerability. Will told me about what he does with projects, and I feel the same way once I’m in it:just go full steam ahead. I don’t really think about it. I didn’t know where everything was going to go with the documentary, but I knew I was going to be in. I was not going to be necessarily comfortable, but I was going to go there. 

Will Ferrell: We thought about all the ramifications and all the potential, things that could or could not happen. But once we decided to go forward  for better or worse there’s no turning back. I was worried that this was going to get emotional at times. I didn’t know where or when or how, but I just had this feeling that as I heard about what my friend went through, the struggles and the courage it took to get to this place,  I was like: “God, this is going to get emotional!” I was afraid of that, but.  But in the end, I am so happy that I did it  

Q: Last question: what is this obsession with Dunkin’ Donuts?  

Will Ferrell: I’m not going to ask that question.  What’s so funny is that I have probably been in a Dunkin’ Donuts three times in my whole life.  We were just driving along and I spotted that sign from a distance and that’s what we do: something hit me where I was like: “I’m going to throw a tantrum right now and talk about how in this trip we haven’t done one fun thing and I just want to go to the Dunkin’. I knew that would make her laugh. That’s all we do. We are always thinking of the next thing that will make each other laugh. That is just an extension of the games we like to play. 

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