‘Will & Harper’ Press Conference with Stars and Director

(L to R) Will Ferrell and Harper Steele in ‘Will & Harper’. Photo: Netflix.

In the new Netflix documentary ‘Will & Harper,’ which premieres September 27th, director Josh Greenbaum chronicles a cross-country road trip by actor/comedian Will Ferrell and writer Harper Steele, who embark on their journey after Harper comes out to Will as a trans woman.

Longtime friends and collaborators ever since meeting on ‘Saturday Night Live,’ Will and Harper address their own friendship, Will’s questions about Harper’s transition, and the chances of both acceptance and intolerance along the way, especially as they venture into areas of the country where Harper may be the target of hate and misunderstanding.

1) It’s All About Who You Know

(L to R) Harper Steele and Will Ferrell in ‘Will & Harper’. Photo: Netflix.

Before directing ‘Will & Harper,’ Josh Greenbaum directed documentaries like ‘Becoming Bond‘ and ‘The Short Game,’ as well as a number of TV projects and the narrative feature films ‘Barb and Star Go to Vista Del Mar‘ and ‘Strays,’ which is how he came into the orbit of Ferrell and Steele.

Josh Greenbaum: I actually knew them prior to making this doc, 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, called ‘Barb and Star Go to Vista Del Mar.’ He starred in my next movie, called ‘Strays,’ and we’ve been friends for a while. 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.’ Then I was brought into the mix of this incredible story and this incredible film through our producers, Jessica Elbaum and Rafael Marmor.

2) You’ve Got Mail

(L to R) Will Ferrell and Harper Steele in ‘Will & Harper’. Photo: Netflix.

As ‘Will & Harper’ begins, Will Ferrell gets an email from Harper — an email that Harper sent to all her friends — in which she reveals that she has transitioned.

Harper Steele: That’s a tough email to press ‘send’ on. You build up a lot of fear, unnecessarily in my case, which is a privilege that I had. I had friends that responded the right way. But I was very afraid to send that. I’m also a writer. I’m a comedy writer, and I’m arrogant enough to think that I’m always right. But that letter was a different kind of writing. I rewrote it probably a hundred times, you know, over a long period of time, 10 years. That was a very difficult letter to put out in the world.

3) Will Ferrell’s Big Idea

(L to R) Will Ferrell and Harper Steele in ‘Will & Harper’. Photo: Netflix.

Before her transition, Harper Steele loved taking road trips across the country, stopping in funky, out-of-the-way places and meeting new people, but she found herself wondering if she could safely do that again as a trans woman.

Will Ferrell: If you know Harper Steele, you know that one of her great loves is taking cross-country road trips. We started talking about that, and a thought just popped into my head. 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, 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. We’ll go and talk to people, and we’ll film it, and maybe someone will pay for us to take a fun road trip.” And she eventually said yes.

4) The Key to Will and Harper’s Friendship

(L to R) Harper Steele and Will Ferrell in ‘Will & Harper’. Photo: Netflix.

Harper Steele says that there is one thing that has kept her and Will Ferrell’s friendship strong for years.

Harper Steele: Comedy, probably, is what we center our life around. We circulate and spin around each other with jokes all day long. I would say that’s sort of the basis of our friendship. It’s been that way since the day we met because we come from a humor background. I think we wanted to show that life and friendship are messy, but 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, that’s kind of our relationship and I think that is what we wanted to get across.

5) How To Support Trans Kids

Harper Steele in ‘Will & Harper’. Photo: Netflix.

Harper Steele was asked what advice she would give to parents about supporting their trans children.

Harper Steele: Well, personally, I would tell them to vote for the kinds of people that are going to support them. We’re not naming any names today, but I do think we need to keep in mind that politics does have a certain amount of control over the laws and the help that we get as trans people. I would say to any parent, you’re very lucky and you’re very fortunate to have trans children. So get out of their way. Let them be themselves, and they’ll be taking over the world soon enough. Let them be themselves.

6) Kristen Wiig Wrote A Song For The Film

(L to R) Kristen Wiig and Will Ferrell at the 81st Annual Golden Globe Awards, airing live from the Beverly Hilton in Beverly Hills, California on Sunday, January 7, 2024, at 8 PM ET/5 PM PT, on CBS and streaming on Paramount+. Photo: Sonja Flemming/CBS ©2024 CBS Broadcasting, Inc. All Rights Reserved.

Although they ask Kristen Wiig in the movie to compose a theme song for their trip, Will and Harper never actually heard the tune until Josh surprised them with it.

Will Ferrell: We thought it would be a funny running joke even if Kristen never got around to making the song. We were not even sure she was going to do it, and lo and behold, boy, did she ever. We had a final screening amongst ourselves where Josh said, “Can you guys come watch the movie again? I just made some small tweaks,” and he surprised us with her song at the end credits. It was another special moment of joy for us.

7) Will Ferrell’s Biggest Fear

(L to R) Harper Steele and Will Ferrell in ‘Will & Harper’. Photo: Netflix.

Although Will, Josh and Harper were all concerned about what kinds of reactions they’d encounter along the course of the trip, Will was also worried about what was going to happen in the car.

Will Ferrell: We were probably fearful about, could we fill the time every day? Could we talk to each other for six to eight hours a day in a car? And we passed with flying colors. We wouldn’t shut up. Also, I just thought, “Boy, this is going to get emotional at times. I don’t know where or when or how, but I just had this feeling that as I hear about what my friend went through and the struggles and the courage it took to get to this place, I just know this is going to get emotional.” I was kind of afraid of that. But then you go through it, and in the end, you’re so happy that you did.

8) A famous actor and a trans woman walk into a bar…

(L to R) Harper Steele and Will Ferrell in ‘Will & Harper’. Photo: Netflix.

At one point Will and Harper stopped in a bar that on the surface seemed like it would be a dangerous place for Harper. But much to Josh Greenbaum’s surprise, they were welcomed and treated kindly.

Josh Greenbaum: 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 to my camera team, like, “Why don’t you guys hide over here. Put your cameras here.” 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. As you see in the film, I think those prejudices and biases that I had were sort of subverted and not met, in a good way. So a lot of times, we found that adage of “it’s hard to hate up close” to be true.

9) What Will Ferrell Learned On The Journey

‘Will & Harper’. Photo: Netflix.

Will Ferrell didn’t know what to expect from America when he and Harper embarked on their trip.

Will Ferrell: I think what we learned is it’s such a big country, and what I mean by that is that within this country, 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 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 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 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 fantastic. 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.

10) Why did Will Ferrell throw a tantrum about Dunkin’ Donuts?

Will Ferrell in ‘Will & Harper’. Photo: Netflix.

In one of the funniest scenes in the movie, Will and Harper drive past a Dunkin’ Donuts and Will throws a fit when Harper says they can’t stop there.

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

What is the story of ‘Will & Harper’?

When Will Ferrell finds out his close friend (Harper Steele) of 30 years is coming out as a trans woman, the two decide to embark on a cross-country road trip to process this new stage of their relationship in an intimate portrait of friendship, transition, and America.

Who is in ‘Will & Harper’?

Will Ferrell

Harper Steele

(L to R) Will Ferrell and Harper Steele in ‘Will & Harper’. Photo: Netflix.

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