How Will Ferrell became an ally on his transgender friend’s journey

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

Will their friendship change? What made her keep this up for so long? And the big one: “Does she still like trash beer or is she completely into wine now?”

Will invites Harper on a trip across America so they can find out “what all this means to us” and spend time hanging out at bars, eateries, and sports arenas — places Harper always liked to go before her transition but isn’t sure how welcoming she’ll be now.

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

Will told the BBC that 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 his best to stand up for 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 an exciting journey for us,” he explained.

“It was shocking news to receive. And I imagine it will feel the same, in terms of our friendship. But I don’t know for sure.

“Selfishly… I thought this could be a great opportunity for me to ask all these questions… and for Harper to have a chance to educate me.”

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

Harper went on to become head writer and supported Will when some others at SNL initially didn’t feel he was overachieving.

“If it was just payback for me supporting him before, he’d be done by now,” Harper said. [supporting her as a trans woman] far beyond what I gave him.”

She has taken countless long car trips and loves the open road, but this was her first cross-country journey since transitioning.

“Yeah, it was tough,” Harper said.

“And I would like to point out that my experience traveling across the country with a famous actor and camera crew was completely different from a transgender person traveling across the country alone.

“Plus, I have money. I can travel in a safer way. So there’s a lot of things out there that don’t relate to the transgender experience. Am I afraid of what I might find out?” out there? Of course I do.”

In one scene, Harper walks into a bar in Oklahoma that appears hostile. She wanted to try it herself. Will is outside waiting. Most were locals and there were pro-Trump and anti-Biden flags on the walls.

Will joins her, and when Harper is referred to as a man by someone, she corrects them firmly but kindly, which Will supports. And the conversation continued.

But as Harper notes, cameras and famous faces offer some protection in such encounters — there are similar experiences at the track and at basketball games. So does it ensure that everyone they meet is on their best behavior?

“I really don’t know,” Will said. “Yes, it is definitely an artificial environment.

“At the same time, when people ask that initial question of what are you doing here, what are you filming, that question goes away and you start talking to these people in a way that I think will last.” at if there wasn’t a camera there.”

But being in a goldfish tank can also have the opposite effect, as illustrated in a scene in a giant Texas steakhouse where friends stop for dinner.

Will randomly dresses up as Sherlock Holmes (which his fans love) and takes on the 72oz steak challenge. But they quickly began to feel uncomfortable as crowds gathered around to watch his efforts and film them on their phones.

The film featured several derogatory comments about Harper on social media and Will said he felt he had let her down.

The next day, the couple read some posts while drinking beer. “When you transition, you eat a lot of that junk,” Harper said. “Those tweets kept going through my head.”

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

“I think politicians are pushing these things to try to win votes, and I think the press is jumping on it because polarization somehow helps the numbers.

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

While there are obviously some very heavy dialogues in the film, there are also a lot of funny moments (note Dunkin’ Donuts), which the film’s director wanted to showcase.

“I’ve got 240 hours of footage!” Greenbaum said. “They’re very funny people. Even in deeper, more emotional conversations, which, seven times out of 10, they’ll crack a joke in there.

“Comedians are famous for using comedy to hide real emotions, but apparently that fear disappeared early on… I’m not sure how open they would be… But they really got there.”

So Harper still drinks trash beer?

“I don’t know if it’s estrogen or not, but I like wine more now,” she joked.