Harper Steele is an American writer and filmmaker from Iowa City. She worked on sketch comedy show Saturday Night Live from 1995-2008, during which time she was promoted to the role of writing supervisor in the second half of its 26th season in 2001, and later promoted to the role of head writer from 2004-2008. She was the creative director of Will Ferrell’s comedy video website and production company, Funny or Die, in 2008. Steele and Ferrell star in Will & Harper, a documentary directed by Josh Greenbaum following the life-long friends on a road trip across the country. The film opens at FilmScene on Sept. 13 and will drop on Netflix on Sept. 27.
The Daily Iowan: Why did you decide to go on a road trip? Was the plan always to film the journey?
Steele: The idea to do the road trip was Will’s. We went on a road trip because, among my friends, I am known for traveling back and forth across the country hundreds of times. It’s just something I like to do, and Will knew that and wondered if possibly that life would change for me now that I’ve transitioned.
Given your background as a writer, was it difficult to make a documentary and avoid the desire to write skits instead?
When Will thought of the idea, I wasn’t too keen on it because I didn’t like the part about being on camera. Also, he was very wary of being exploitative. He didn’t want to feel like a virtue signaler, you know. It took me a while to think about it, but I got there, mainly because I thought it would be crazy, and Will and I both like to do lots of crazy things. There was a lot of trans legislation and stuff in the news that I wanted to have an impact [on]. Honestly, I was being more exploitative with Will than he was with me. When I got to the point where we said yes, it was our natural impulse to think of bits to do on the road, sketches and bits. It was one of the producers, a woman named Jessica Elbaum, who works with Will who said, “No don’t do that, you guys should just do what you guys naturally do,” and what we naturally do is just talk. And be funny while we’re talking. There was no desire to make any sketches out of it.
What made you choose John Greenbaum, also director of “Strays,” and “Barb and Star Go To Vista Del Mar,” as the director?
It always seems to be left out of many [articles], but he’s made six documentaries. I got to know Josh through Kristen Wiig, who’s in “Barb and Star,” and we’re friends. The reason why we chose Josh was because this was a very vulnerable thing for me to do. I couldn’t have a stranger direct it. I needed it to be someone that I knew and spoke my language. My language even in intimacy is comedy, and Josh was familiar to me.
How exactly did you and Will Ferrell meet? What has your relationship been like up to this point?
Thankfully, it’s pretty much unchanged, and it got deeper through this process because Will is a good friend and an ally and wanted to ask me about what I was going through. We met at Saturday Night Live in 1995. We were both hired the same week, I as a writer and Will as a performer and a writer. We’ve been friends for almost 27… 28 years I don’t know. But the relationship has always been besties.
How does spending time with a good friend differ when it’s on camera vs off camera?
For us, if you watch the documentary, it’s exactly how we are at all times. The first couple of days were uncomfortable because not even Will is used to cameras following him as Will. I certainly am not used to that either. But Josh, he’s done a bunch of docs and said that after day two or three, they all disappear, which neither of us believed. But that did happen, we got very comfortable, and what you’re seeing is exactly how we communicate now, and forever. It’s just comedy. That’s where we live.
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Do you believe that you and Will have a stronger friendship now that the movie is finished?
I’m sure we do. I couldn’t have had the strongest of friendships with anyone because I was holding a part of myself from people. I think friendships are formed with honesty. I’m not saying I was dishonest, I was repressed or afraid, but I think friendships deepen when people are honest, and it has changed for the better.
What was your favorite part of filming this movie and why?
I love Iowa City, I really do. I grew up there, I go there often, and my sister still lives there. I’ve been back, but just coming into that town, experiencing it the way I was supposed to have experienced it, is thrilling for me. I don’t think it’s everyone’s favorite moment in the doc but there are a lot of fun moments that happened. [Going to Iowa City] was a very personal moment and I enjoyed it
What about your story felt important to share with the world?
This is a roadmap for friends to discuss difficult issues in general, not just transitioning. What happens when good friends communicate with each other the way they probably should? And obviously, I hope it is a way for families and people to think about trans people in their own families and communities and feel more aligned with those people.
When did you know transitioning was part of your path in life?
It’s been a part of my life since I was born. I think the pathway started to open up about 12 years ago. It would be a complicated mess for me to try to explain what happened before that.
How do you feel now, so close to the movie’s release on Netflix and at FilmScene in Iowa City?
A little nervous. Again, I’m not an actor. I will not be making more movies as an actor. To see yourself projected sixty feet tall is — on top of the dysphoria I sometimes feel about myself — just looking at yourself on film like that is nerve-wracking. But then also, like I said, Iowa City is a special place for me and I’m just hoping it’s warmly received there.