Here's a Weird One: Will & Harper - FilmInk
by Gill Pringle
Will Ferrell is under no illusion that documentaries actually make money, but his new doco Will & Harper comes straight from the heart and there was no way he could not make it.
It all began when he received a surprising email from a dear friend of almost 30 years – who was coming out to him as a trans woman.
That friend was Harper Steele, a writer he met on his first day at Saturday Night Live back in 1995. From that fateful first meeting in the halls of 30 Rock, Ferrell knew he had found a match made in comedy, their friendship and creative partnership continuing to grow over the next three decades.
Naturally, he immediately responded to the email and had a lot of questions.
“If you know Harper Steele, you know that one of her great loves is taking cross country road trips, and she’s done it as long as I’ve known her and she was lamenting the fact that, after a transition and as a trans woman, if she could still feel safe enough to go into some of these little out of the way bars and places or even rest stops,” recalls Ferrell, 57.
“So, we started talking about that, and a thought just popped into my head – and 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… Cha ching!” jokes the actor, celebrated for comedies such as Elf, Anchorman, Old School and Step Brothers.
“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, because 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. But at the same time, we can go to these places, and I’ll kind of be your buffer, and we’ll go talk to people, and maybe it’s a way to kind of kill two birds with one stone. And we’ll film it, and maybe someone will pay for us to take a fun road trip’. And she eventually said yes,” he recalls when FilmInk meets with Ferrell and Harper Steele herself.
A firm believer in changing hearts and minds through comedy, Steele says: “I think that, because we come from a humour background, we wanted to show that life is messy with friendship, and 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. I mean, that’s certainly our kind of relationship, so we wanted to get that across.”
She hopes their documentary sheds light on an issue that is still uncomfortable for some people.
“I think there needs to be a lot of forgiveness for people in this world, who aren’t familiar with trans people and queer people. We’ve been in this world for thousands and thousands of years so let’s get over that.
“But yeah, I’m hoping the audience takes something very positive away from this about trans people, and about friendship and how friendship works,” she adds.
Directed by Josh Greenbaum, the trio set out on their road trip with certain trepidation, understanding how the U.S. is a huge country, and peoples’ views can be polarizing; amply demonstrated by a scene where Steele visits an Oklahoma bar festooned with confederate flags and vulgar anti-Biden posters.
“But I think what we learned is it’s such a big country but within that, 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 than we don’t,” argues Ferrell.
“But 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 kind of push through.
“At the same time, we ran into some lovely people who were not threatened in any way by Harper. And they were fantastic: ‘You do you!’ or ‘I see you!’ and ‘Come back again!’ 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,” he concludes.
Sending that original email where she came out to all her friends was not easy for Steele who had progressed to SNL’s head writer, coming up with comic sketches for the likes of Kristen Wiig, Will Forte and Tina Fey.
“That was a tough email to press ‘send’ on,” she recalls. “You’ve built up a lot of fear – unnecessarily in my case. So that’s a privilege that I had. I had friends that responded the right way, but, yeah, I was very afraid to send that. I’m also a comedy writer, so I’m arrogant enough to think that I’m always right, and when you write that letter, that was a different kind of writing. I rewrote it probably a hundred times over a long period of time, ten years maybe. It was a very difficult letter to put out in the world,” says Steele, 62, who used the subject line: ‘Here’s a weird one . . .’
“And then, my goal after I transitioned was to see if the country still loved me, or if I still loved the country – and I still love my country,” she says.
Making the documentary was not an easy decision. “I was hesitant at first, so I had to think about that. I don’t like being on camera, and yes, it was opening myself up to a lot of vulnerability.
“But I think Will has said this about when he does projects, and I feel the same way once I’m in it, is that you’re at full steam ahead and I don’t really think about. I didn’t know where everything was going to go – it’s a documentary after all – but I knew I was not going to be necessarily comfortable, but I was going to go there,” she says.
As much as Will & Harper is an exploration of the life of a newly trans woman via a road trip documentary – it is also a sweet story about the power of enduring friendship.
Will & Harper is streaming now
