When trans woman and longtime comedian Harper Steele walked into a hostile-looking Oklahoma bar, what happened next shocked everyone.
One fateful day in 1995, future Hollywood A-lister Will Ferrell, 57, arrived at New York’s NBC studios (aka 30 Rock) to walk the hallowed Saturday Night Live halls that the who’s who of the comedy world has passed through at one point or another.
Here, he met Harper, 63, then a young comedy writer who shared an instant spark with Will. One that has stood the test of time over the past three decades.
Then, during the pandemic, the Anchorman star received an email from Harper in which she revealed she was a trans woman and wanted him to know as she started living life as her authentic self.
After his instant acceptance, Will was left not only with questions about Harper’s identity but what it meant for their friendship. Did she still like the same beer and truck stops? Would their comedic chemistry remain the same or be inexplicably changed?
And so the dynamic duo set off on a cross-country road trip – documented in the new Netflix film Will & Harper – filled with constant riffing, the usual dingy haunts Harper knows and loves and a tender vulnerability rarely seen by the Hollywood elite.
In the two-hour documentary, the pair revisit significant places in Harper’s life, from a sports game in Indianapolis to her childhood home in Iowa City, as they confront the reality of navigating often Republican spaces as a trans woman.
There are plenty of tense moments, including a strained steak dinner in Texas which they pulled out from early, and an unwitting interaction with an anti-trans governor.
But there is one moment during filming (which produced over 240 hours of footage that had to be ruthlessly chopped) that has stayed with director Josh Greenbaum long after he cut the cameras.
‘I think the moment that hit me hardest while we were filming was when we went to the bar in [red state] Oklahoma,’ Josh told after the UK premiere of Will & Harper.
He continued: ‘I walked in [and] there was a confederate flag, there was some political signage that made me feel that this was not going to be a safe environment. But Harper insisted she wanted to go in on her own.’
There’s no doubt about the initial hostility in the air – with ‘f**k Biden’ and pro-Trump posters scattered on the walls – as Harper tests the waters and the patrons emanate an intense curiosity only the hardiest of people would be able to bear for long.
But then a switch flipped – and everything changed.
‘She went in and after a while was met with not just acceptance, but degrees of love that was so heartwarming,’ Josh explained.
Soon enough a pair of Native American customers start performing music for Harper and when Will enters the equation the level of comfort and genial conversation only increases.
It was an overwhelming night for all involved.
The Emmy-winning director added: ‘The thing that really floored me was, after we walked out of there and we went to a dirt racetrack, she had a little bit of a moment and started crying and saying, “I think what I’m afraid of is not people hating me, but me hating myself”.
‘And that was really hard to hear as a subject of my film, but also as a friend.
‘I think that’s something that you know we all have to recognize is when you are raised in a culture that has a lot of anti-trans messaging.
‘Of course, she has [internalised] transphobia. So the journey of the second half of the film really became her figuring out a way to love herself, which I think she did through the help of her close friend Will.
‘So that was a moment that really hit me hardest. It was a good 20 minutes of crying myself, and I think I was still crying after them, and they were like, “come on, Josh, get it together”,’ he added with a smile.
It’s not surprising that the moment was so moving considering the recent swathe of anti-trans bills sweeping several states across the US, including a push for the ban of gender-affirming healthcare for minors.
Josh had nothing but praise for the way both Will and Harper embraced the project which, at times, demanded huge amounts of vulnerability.
‘They have a shorthand and they’re incredibly funny,’ he said about their dynamic.
‘They’re just some of the best comedians of my lifetime and so they’re constantly trying to make each other laugh. But what was beautiful to watch was, as the trip went further and further, they got more and more comfortable being vulnerable and opening up to one another.’
And he hopes cis allies can learn a lot from their approach, that sometimes it’s as simple as ‘pulling up a chair or going for a drive or a road trip with those who may need it most, and being present and being there.’
Although Josh could see the vision of this film early on, it couldn’t have been more different for the subjects of the film who were just doing comic bits and hoping for the best.
‘There was no sense of what we were doing. In fact, Will and I, when we got to the end, pretty much felt like we didn’t have anything,’ Harper admitted.
And Will echoed her words: ‘For Harper, it took a great amount of consideration to even agree to do it, to come around but I think once we decided to jump in, you’re just along for the ride.
‘There wasn’t a lot of speculation, other than literally sitting at the beach [at the end of the film] and going “Well, I hope there’s a movie there”.’
As veterans of the comedy industry, both Harper and Will are all too familiar with the pitfalls of anti-LGBTQ+ comedy prevalent in Hollywood – especially in the 90s and 00s.
In fact, Will has previously expressed regret over dressing up in drag for an SNL sketch but believes the comedy industry as a whole is on an upward trajectory.
‘I think there is growth and evolution [in the comedy industry] in a very positive way. And there’s definitely things I look back on in my career and say, “oh, I definitely would not do that now”, but that’s part of the process,’ he told us.
When asked whether the tide is turning in Hollywood when it comes to amplifying trans stories, the pair remain realistic and humble.
‘Of course not,’ Harper scoffed.
As Will added: ‘We’ve created this, and we’re talking about this, and we’re putting this out in the world, so there’s one more story.’
And for Josh this has all been worth it to see Harper finally getting her flowers after years of having to hide herself away from the world.
‘I’m watching Harper now at these screenings, get standing ovations, and it’s such a beautiful thing that she was brave enough to make this decision late in life to really try to live her true, authentic self, and now she’s being celebrated for it,’ he concluded.