How Will Ferrell became his road trip buddy

When Hollywood star Will Ferrell received an email from his old friend Harper Steele a few years ago, telling him he was transitioning to live as a woman, he had a lot of burning questions.

Will their friendship change? What made him keep this up for so long? And biggie: “Do you still like trash beer or are you totally into wine now?”

Will invites Harper on a road trip across the US to find out “what this means to us” and spend time hanging out in bars, restaurants and stadiums – places Harper was always excited to go before the transition but wasn’t sure. how can he be accepted now.

Their 16-day journey from New York City to Santa Monica, California, is the subject of Josh Greenbaum’s new Netflix documentary Will & Harper.

Will tells the BBC that he began to think more about how to support Harper after he sent her a follow-up email announcing her name and asking her to “do everything she can to represent me”.

“If I’m really as good a friend as I think I am to him, I want to show him that [support] which I hope will be a happy journey for us,” he explained.

“It was kind of shocking news to find out. And I thought it would be the same, in terms of our friendship. But I didn’t know for sure.

“Selfishly… I thought this would be a good opportunity for me to ask all these questions… and give Harper a chance to teach me.”

The two met when they were both hired for the same week by the US TV show Saturday Night Live back in 1995.

Harper went on to become a head writer and championed Will when others at SNL didn’t feel he was making the grade at first.

Harper says: “If it was just payback for my support before, he would be done by now [supporting her as a trans woman] it is far more than what I gave him.”

He had been into long road trips and loved the open road, but this was his first cross-country trip since his conversion.

“Yeah, it’s scary,” Harper said.

“And I would like to point out that my experience traveling with a famous actor and a camera crew is very different from someone traveling alone across the country.

“And I have money. I can travel safely. So there’s a lot out there that doesn’t talk about the trans experience. Was I afraid of what I might find there? Yes, I was.”

In one scene, Harper walks into a hostile-looking Oklahoma bar. He wants to try it on his own. Will is out of abeyance. Most of them are residents and there are pro-Trump and anti-Biden flags on the walls.

Will joins him, and when Harper is called a man in the introduction, he corrects them firmly but kindly, with Will’s support. And the conversation continues.

But as Harper points out, cameras and famous faces provide some protection during such encounters – there are similar experiences at the racetrack and at the basketball game. So did it ensure that the people they met behaved very well?

“I really don’t know,” Will said. “Yes, artificial nature for sure.

“At the same time, people asked the first question of, what do you want here, what are you recording, it melts and you start talking to these people in a way that I think would have happened if they were not there. the cameras are there.”

But being in a bowl of goldfish can also have the opposite effect, as shown in the scene at a large Texas steakhouse where friends stop for dinner.

Will randomly dresses up as Sherlock Holmes (the kind of food shown to his fans) and tries the 72oz steak challenge. But it quickly starts to feel uncomfortable as crowds gather around them to watch his attempt and capture it on their phones.

The film brings out insulting comments on social media towards Harper, and Will says he feels humiliated.

The next day, the pair read another post about beer. “Once you’re over it, you eat a lot of junk,” Harper said. “Those tweets are stuck in my head.”

Harper tells the BBC she is “very aware” of the toxicity in the mainstream transgender/gender debate.

“I think politicians are pushing these things to try to get votes, and I think the media is jumping on it because segregation somehow helps the numbers.

“And I understand that there are people in their basements and people who are angry and want to evict. But in everything, I believe that people are kind, and letting someone live their truth should be everyone’s goal.”

While there’s obviously some serious dialogue in the film, there are plenty of funny moments too (watch out for the Dunkin’ Donuts), something the director was keen to promote.

“I had 240 hours of footage!” Greenbaum says. “They’re very funny people. Even in deep, emotional conversations, naturally, seven times out of 10, they can make a joke within that.

“Comedians are famous for using their humor to hide real feelings, but obviously that fear quickly disappeared… I wasn’t sure how much they would open up… but they really went there.”

So is Harper still just drinking trash beer?

“I don’t know if it’s estrogen,” she jokes, “but I like wine now.”