How Will Ferrell Became His Trans Friend’s Road Trip Ally

When Hollywood star Will Ferrell received an email from his old friend Harper Steele a few years ago telling him that she was becoming a woman, he had many burning questions.

Will their friendship change? What made her keep it up for so long? And most importantly: “Does she still like trash beer or does she totally like wine now?”

Will invited Harper on a road trip across the United States so they could understand “what this all means to us” and spend time hanging out at bars, restaurants and sports arenas – places where Harper had always liked to go before transitioning, but wasn’t sure about it. how welcome she would be now.

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

Will tells the BBC he started thinking more about how he could support Harper after she sent him a follow-up email announcing her name and asking him to “do your best to defend me” .

“If I’m really as good a friend as I think I am to her, I want to show her that (support) in what I hope will be a fun journey for us,” he explains.

“It was shocking news to receive. And I thought it would be about the same, in terms of our friendship. But I wasn’t sure.

“Selfishly…I thought this might be a great opportunity for me to ask all these questions…and give Harper the opportunity to educate me.”

The two met when they were both hired in the same week by the American television show Saturday Night Live in 1995.

Harper then became editor and defended Will when other people at SNL didn’t think he quite hit the mark at first.

Harper says, “If this was just a reward for my support earlier, he would be done by now. This (supporting her as a trans woman) is way beyond what I gave him.”

She had taken countless long road trips and loved the road, but this was her first cross-country trip since her transition.

“Yes, it’s intimidating,” Harper says.

“And I like to point out that my experience traveling across the country with a famous actor and film crew is quite different from that of a trans person traveling across the country solo.

“Plus, I have money. I can travel more safely. So there’s a lot of stuff out there that doesn’t speak to a trans experience. Am I afraid of what I might find out there? Of course I was.”

In one scene, Harper walks into an Oklahoma bar that appears potentially hostile. She wants to try it for herself. Will is outside, waiting. It’s mostly locals and there are pro-Trump and anti-Biden flags on the walls.

Will joins her, and when Harper is called a man by someone during the presentation, she firmly but kindly corrects them, supported by Will. And the conversation continues.

But as Harper points out, the cameras and the famous face offer some protection during such encounters – similar experiences happen on a racetrack and at a basketball game. So, did this guarantee that the people we met behaved better?

“I don’t really know,” Will said. “Yes, it’s an artificial environment, that’s for sure.

“At the same time, once people ask that initial question, what are you doing here, what are you filming, that disappears and you settle into a conversation with these people of a way that I think would have existed if there had been “There are no cameras there.

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

Will randomly dresses as Sherlock Holmes (the kind of antics his fans love) and attempts the 72-ounce steak challenge. But it starts to get uncomfortable pretty quickly as crowds gather around them to watch his attempt and film it on their phones.

The film reveals disparaging comments on social media about Harper, and Will says he feels like he’s let her down.

The next day, the two men read some messages over a beer. “When you’re trans, you ingest a lot of this garbage,” Harper says. “Those tweets stick in my head.”

Harper told the BBC she was “acutely aware” of the toxicity of much of the transgender/gender debate.

“I think politicians push these things to try to get votes, and I think the press seizes on it because somehow polarization helps the numbers.

“And I understand that there are people in their basements and people who are angry and want to lash out. But overall, I believe people are kind, and letting a person live their truth should be everyone’s goal.”

While there are obviously some very heavy conversations in the film, there are also a lot of hilarious moments (watch out for Dunkin’ Donuts), which its director wanted to highlight.

“I had 240 hours of images!” Greenbaum said. “They are very funny people. Even in the deepest, most emotional conversations, seven times out of ten they would make a joke within it.

“Comedians are famous for using their comedy to mask real emotions, but obviously that fear disappeared early on…I wasn’t sure how much they would open up…but they definitely go for it.”

So, does Harper still only drink trash beer?

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