Will Ferrell talks about the trans-documentary “Will & Harper”

NEW YORK – A road trip with Will Ferrell is just as fun as you could imagine.

In the Netflix documentary “Will & Harper” (now streaming), the comedian travels across the country with his best friend Harper Steele, who came out as a trans woman in 2021 at the age of 61. Together they embarked on a 16-day road trip from New York to Los Angeles: visiting national landmarks, jamming to alternative rock while drinking Pringles and McDonald's coffee.

Whenever they got bored, “I'd call the number on a billboard that said a personal injury lawyer,” Ferrell recalled cheerfully as he ate lunch of salad and croissants one afternoon. “There are hours of footage of this – it really made us laugh.”

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How 'SNL' Rekindled Will Ferrell and Harper Steele's 30-Year Friendship

The longtime friends met in 1995 when they were both hired on Saturday Night Live in the same week (Ferrell as a cast member, Steele as a writer). They quickly discovered that they had similar temperaments and comedic sensibilities. Amid the chaos of Tuesday night writing sessions, they often holed up in Steele's office, chatting and listening to records.

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“I was a little upset, but I'm subdued,” said Steele, sitting on a couch next to Ferrell. “Will is a very gentle and reserved person to the point where you have to be the other person, so I think we just clicked.”

After “SNL,” they continued to work together on comedies like “Casa de mi Padre” and “Eurovision Song Contest: The Story of Fire Saga” until the COVID-19 lockdown. During this time, Steele came out to her close friends and family via email. Knowing how much she loved greasy spoon restaurants and dingy dive bars in the heartland of America, Ferrell suggested a road trip so she could revisit those places where she now lives as a woman.

Steele initially declined to film their outing. “I don’t like being in front of the camera for some reason,” she says. But after thinking about the idea for a few months, she thought about what the documentary “could mean in terms of politics and the trans landscape in America and any (anti-trans) laws that get passed.” I thought , there would be something valuable. Plus, every time I work with Will we do weird projects. This one felt uncomfortable and strange.”

Ferrell also had his own fears about the very personal film: Steele gives him free rein to ask her all about life as a trans woman, her decades in the closet and her struggle with self-hatred and insecurity. They're also venturing into conservative parts of the U.S. where trans people often face prejudice.

“I was afraid of, ‘Am I asking the questions right?’” Ferrell, 57, remembers. But also, “Are we going to have a crazy confrontation (with someone) out there?” And when people inevitably ask what we're filming, can I stand up for my friend and articulate what's going on? All these things were going through my head.”

Harper Steele doesn't want to be afraid as a trans woman

Partly because of Ferrell's celebrity, most of her interactions with strangers are warm and cajoling. But the film also forces viewers to confront the bigotry that Steele faces as a trans woman: In one scene, she receives cruel comments on social media after sitting courtside with Ferrell at a basketball game in Indianapolis. Even dinner at a steakhouse in Texas turns into an unpleasant nightmare when Steele is mistreated and stared at by the restaurant guests.

“I just want to be able to be in these places because I don’t hate them. I don’t want to be afraid of them,” Steele said. “Basketball games in the middle of the country are things I want to see and I should be welcome there. And I can't say if I'm really welcome there because I was there with Will Ferrell. With Will Ferrell you’re welcome everywhere, so it’s not necessarily a real trans experience.”

Since filming, she has traveled alone across the Midwest without the camera rolling.

“I found it easier,” Steele says. “Part of it is because of me and the confidence I bring with me now when I go to these places.” But people in general “aren't interested in being mean to begin with.” They're interested in being kind, and when they come home to their basement, they may feel like they have to say mean things.”

Will Ferrell and Harper Steele hope their Netflix documentary will “do some good.”

Many Oscar experts expect “Will & Harper” to be nominated for best documentary. The film is part of an exciting new chapter for Ferrell, who, along with producing partner Jessica Elbaum, has helped helm women-centric films such as May December, The Menu and Am I OK?

“We're just trying to lend the money we have to the voices that maybe aren't getting as much support as they should,” Ferrell said. “That’s kind of the rallying cry, and it’s so fun when these things actually get traction.”

Ferrell says he's already received text messages from friends saying, “I didn't really know what it meant to be trans,” and that they now know how to better support other people transitioning. Steele also hopes the film will do “something good in the queer community.” Now living in LA, she sees Ferrell more regularly and is grateful for the “care” he showed her. Had she come out as transgender decades ago, she may never have been hired on or become friends with “SNL,” Steele suspects.

“Any person who comes out later may feel regret, and you can decide whether or not you want to move forward with it,” Steele says. “I just don’t do that. I have no interest in living with resentment.”

Will Ferrell talks about the trans-documentary “Will & Harper”

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