How a cross-country road trip brought Will Ferrell closer to his trans bestie Harper Steele

Will Ferrell and Harper Steele talk about each other the way only decades-long friends can. Interspersed with the effusive praise they give each other and the fond memories they share are lighthearted jabs and barbs, always with love behind them.

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That’s how it’s been since the two met when they both started at Saturday Night Live the same week back in 1995. But when Harper came out as a trans woman during the pandemic, the two comedy legends were afraid that might all change.

Would they no longer be able to joke? Would they have to tiptoe through a minefield of hot topics during every conversation? Would they drift apart? The opposite came true.

courtesy Netflix

Scenes from the Netflix documentary "Will & Harper"courtesy Netflix

“I’ve never seen her more relaxed, more open, and more outgoing,” Ferrell says of Steele. “She is someone now who jumps right into engagement. There’s just a lightness to her that brings me such joy. Don’t get me wrong, she still makes fun of me and is beautifully acerbic … but she’s filled with light and joy.”

Ferrell and Steele’s friendship is the subject of the documentary Will & Harper, coming to Netflix September 27. The film follows the pair as they go on a cross-country car trip (something Steele has loved to do her whole life), stopping at dive bars, rodeos, and roadsides shortly after Steele came out to Ferrell.

The two have been tight friends ever since SNL, when Ferrell was considered the rough-around-the-edges new guy and Steele loved writing sketches for him. Eventually, Steele became a head writer, having that role from 2004 to 2008. When they both left SNL, they worked together at Funny or Die, where Steele was creative director, and she went on to write off-kilter but underrated movies for Ferrell like the Spanish-language Casa de mi Padre and 2020’s Eurovision Song Contest: The Story of Fire Saga.

courtesy Netflix

Their shared sense of humor got them through a lot, and now both have said that humor helped them bond after Steele came out, something that pushes up against the conservative talking point that trans people can’t take a joke.

“That clearly is on both sides. There are people who start crying if you call them cis,” Steele points out. “But there isn’t a trans person I’ve met who doesn’t have a sense of humor about themselves.”

“My advice would be to not be afraid to ask questions, no matter how stupid you think they may be,” says Ferrell, who has made a career out of looking stupid for laughs. “The other recommendation is to just listen. Sit back and listen to their story, their journey, and try not to assume anything. It will all feel strange but it’s exciting to learn about your friend in a completely different way.”

“I think it helps that Harper and I have known each other for close to 30 years and we really got to know each other through the language of comedy,” Ferrell says about their ability to joke. “I also think we only really tease and joke about the ones we love the most. I believe that as long as there is a base of sensitivity and understanding, some gentle teasing helps demystify the topic.”

courtesy Netflix

In between laughs, Ferrell and Steele also worked through some emotional moments while on the road.courtesy Netflix

“I think that’s the dividing line for me. My humor in general is not mean-spirited ... I don’t like to punch down,” Steele says. “I do think trans people — although we are superior — are thought of sometimes as inferior. And so for a lot of people and culture in general, when they’re talking about trans people and making fun of trans people, they are punching down. That to me is a cowardly thing to do.”

“If you’re friends with [a trans person], laugh with them about what they’re going through. I mean, I laugh about my bodily changes, my life all the time,” she says. “I don’t think there’s not a serious side to this, but also it’s my nature to be comic.”

Steele and Ferrell’s humor flows freely throughout the documentary, and any fan of either will find plenty to laugh at here. That alone should convince most of America to watch it.

Whether you’re from New York, California, Indiana, Ohio, Texas, or Kentucky, Will Ferrell will make you laugh. Although her name isn’t as big, if you watched SNL or Funny or Die at any point in the last three decades, Steele has made you laugh too.

“Will is funny,” Steele says. “I’m funnier, but I hope people watch it because it’s a funny movie.”

courtesy Netflix

“I mean, that’s the glory and the power of my friend Will. I think politically there are people who probably do not align with him and might hate him on some level because of his liberal politics. But I don’t think there’s a person out there of a certain age group that wasn’t touched by either Elf or Talladega Nights or Anchorman,” she adds. “The country as a whole, I think, likes seeing him.”

That’s good, as Will & Harper could be one of the most important films of the year.

While the country as a whole loves Ferrell, not all of it loves trans women, and that’s one of the reasons the two traveled together — Steele felt apprehensive about traveling alone through small towns and red states as a trans woman.

Across the country, more than 550 anti-LGBTQ+ bills were introduced in 43 states last year, and more than 80 were passed into law. In some states, Harper wouldn’t be able to use certain public restrooms, while in others, businesses could turn her away just because of her gender.

courtesy Netflix

Since the movie was made, Steele has never been happier. She’s working on a Netflix show, enjoying life, and looking for her next opportunity for a road trip. She glows with excitement when she talks about it.

But Steele also knows that trans issues have only gotten more incendiary since she came out, and the atmosphere will get more heated as the election nears. While she’s dealt with transphobia her whole life, she doesn’t think she’s ready for the onslaught of hate headed her way when the documentary finally releases.

“Yes, I want it to be positive and I want it to be a positive influence on my life, to be selfish, but I know I’m going to get destroyed online, I know.” she laments. “Any out-front trans person is relentlessly killed online by the weirdest subset of people in our culture who obsess over things like this. They are a small group, I believe, I truly believe, but they are the loudest group online.”

“And they do wield influence in an ugly and subtle way, and it finds its way into laws and courts and makes my life — and especially the lives of people without my privilege — especially difficult,” she adds. “I’m very proud of it. I’m scared of, like you say, the aftermath of it coming up, but I’m very proud.”

She should be.

Will & Harper premieres September 27 on Netflix.