The Story Behind 'Will & Harper,' as Told by Will and Harper

I n Will & Harper, actor-comedian Will Ferrell and renowned writer Harper Steele embark on a cross-country trip as inseparable friends and creative partners of nearly three decades. Theirs is the kind of bond that speaks the language of comedy fluently, when it requires spoken words at all.

Still, their longtime camaraderie was at the start of a brand new chapter when they set out to make the movie. Just three years ago, Steele came out to Ferrell as a trans woman in an unexpected email. Ferrell immediately offered his support. Later, knowing Steele’s lifelong love of road trips , he pitched her an idea: “What if we do a road trip where we discuss what this transition means for us?” It was important to him that Steele know he wasn't trying to exploit their relationship for content. He just saw it as an opportunity for them to talk things through, for him to ask questions, and for her to revisit places that have always been a part of her life—but this time, living openly as a trans woman.

Steele said yes, and their cross-country adventure between New York and L.A. (with stops that included Iowa, Oklahoma, New Mexico, and Texas) eventually became the Josh Greenbaum-directed documentary Will & Harper , a nostalgic, heartfelt, and witty road movie, and one of the most beautiful films about friendship ever made. The film by Greenbaum (best known for the 2021 comedy Barb and Star Go to Vista Del Mar ) organically captures the duo’s vibe, charged by similar temperaments and a sense of humor fully in sync ever since they met at Saturday Night Live in 1995.

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A friendship forged under pressure

“I liked Will, because his way of being in the world was relaxing to me,” Steele recalls of their early encounters during our sit-down at the Telluride Film Festival, where Will & Harper screened to adoring audiences before its limited theatrical run on Sept. 13 and Netflix launch on Sept. 27. “I get a little nervous around big comedians trying to make you laugh all the time. Will wasn't doing that. We were at a volume that was much lower. I like that volume.”

“I loved what a grouch she was,” Ferrell adds with a chuckle. “ Saturday Night Live can be a frenetic place. And then I go by Harper's office, she's there with feet up on the desk, listening to a record while everyone's running around.” [To Steele:] “You were probably procrastinating.”

“I was procrastinating.”

From those long work hours emerged a shared impulse to make fun of the notoriously high-pressure environment on the show. Every now and then, Steele would slip an “urgent” message to Ferrell during rehearsals that just read, “ Don’t blow it! ” “Putting a lot of stake in everything being the best thing ever is just pointless. You don't write comedy that way,” Steele reflects.

The ease she speaks of, and the effortless rapport through which Steele and Ferrell have always engaged with one another, drive much of Will & Harper . The movie plays not as a collection of forced gags, but as a documentary-style hangout comedy starring two very funny and deep-thinking pals who enjoy each other’s company over an endless supply of Pringles. Ferrell recalls, “We had a meeting with Rafael Marmor and Jessica Elbaum, two of our producers. And Jessica was like, ‘You guys should just do this the way you're joking with each other right now. It should just live right there.’”

That off-the-cuff energy at the heart of the film also shines through in our interview. Just beneath their bickering lies the finest sort of friendship, one laced with as much droll sarcasm and self-deprecation as honesty and vulnerability. “Comedy is my language of love,” says Steele. “It is the only way we know how to converse,” adds Ferrell. “What's wonderful about the documentary is that we get into very earnest and serious discussions about the questions I have about what Harper's going through. And then there is a funny remark, but not on purpose. It was a lot of times led by Harper making fun of me for not being an A-list actor. You're with an A-list actor right now. You realize that, right?” Ferrell jokes.

“No, I was not,” Steele deadpans. “But you are an a-hole.”

“A for a-hole,” laughs her friend.

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Ups and downs across the country

In planning the itinerary, the priority was hitting spots that were meaningful to Steele. One was Iowa City, where she grew up. Fitting in a basketball game was crucial too, as going to basketball games ultimately helped form a significant part of their friendship. Then came other scenic ideas like the Grand Canyon that any self-respecting road tripper should at least consider. The shoot yielded 200 hours of footage, and the duo say they completely trusted Greenbaum with it. “He cut it the way he felt and saw it,” Steele says. “He made such wonderful choices,” Ferrell agrees. “And he found an amazing DP [Zoë White] who mostly comes from the narrative world.”

The result of those creative decisions is a classically cinematic look and feel, which excites the duo. “I’m sure other docs that feel [this cinematic] exist. But I’m very proud of that in our movie,” Steele explains. “And I like that Josh is funny like us. But not as funny as us.”

“There's no way,” Ferrell concurs with a grin. “Make sure you leave that in. Not as funny.”

The trip wasn’t always smooth sailing. Amid all the pleasant encounters and family visits, there was an experience at a steakhouse in Amarillo, Tex., where they were met with hostility. The transphobic social media attacks that came after, also included in the film, were equally painful. As Ferrell puts it, one of the themes of the movie is whether the country that Harper loves so much loves her back. The answer that the Amarillo experience offers is a distressing one .

Still, Steele wants to carefully emphasize what Will & Harper is and isn’t when it comes to trans visibility. “I am very uncomfortable with [referring to] this film as a representation of all trans people ,” she explains. “There are trans people and LGBTQ people of different backgrounds, race and class. What we represent is the power of the kinds of conversations that we should all be having. The hope is for people to recognize that they do have a queer person somewhere in their family. How are they thinking about treating that person? Maybe a film like this can show the way to do it with comedy.” Ferrell continues, “We're just talking in the film, it's as simple as that. You see me struggling with how I phrase certain things at times. ‘Am I asking it the right way?’ Hopefully the film will demystify just having a conversation about it.”

Learning to be vulnerable and take action

Has their friendship evolved since the making of Will & Harper ? “Evolved is not the word I would use. Devolved,” Steele jokes. “We don’t want to be around each other.” Ferrell laughs, “It’s devolved. I'm waiting for her just to buy dinner at least once in my lifetime.” Setting the gag aside, Ferrell continues, “There's no big evolution. We’re still hanging out. We went to a soccer match a couple of weeks ago. We're just kind of doing our thing.”

“We’re easy travel companions. Maybe we’ll go somewhere again at some point,” Steele says.

And what have they learned throughout this journey? “To be vulnerable is a very powerful position,” Steele says. “A lot of times, our friendships are built in ways that vulnerability isn't allowed. And once that vulnerability is allowed, it just opens up the friendship to new and better places.”

Seconding Steele, “I thought I was an evolved person who wasn't afraid to be vulnerable,” Ferrell continues. “But this was a whole different experience. I hope people understand that it's really important for us not to pay lip service to advocacy for our friends, but to actually take action.”

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Steele spelled out how she views this kind of action in an email she sent to her friends about her name change. “I’m not a political person by nature, but now as a trans woman, I am in a political arena whether I like it or not,” she wrote. “I just ask you to please stand up for me. I am Harper. My pronouns are she/her. And if someone misgenders me, it doesn't have to be a big deal. But just please go, ‘No, no, you mean her . You mean she .’” And Ferrell remembers thinking, “OK, I’ll take this to heart.”

“It’s hard,” Steele says. “A bunch of guys, friends my age, might be sitting there away from me, going, ‘Apparently he's Harper now, and likes to be called she. And so we should be calling her she.’ They might not be quite there. But Will got there very quickly. He is a C-level actor, but an A+ human being.”

“That's what we're trying to say,” Ferrell nods. “I'm C-list, but I'm an A-level human.”

Contact us at letters@time.com .