NEW YORK – Going on a road trip with Will Ferrell is just as entertaining as you would think.

In the Netflix documentary “Will & Harper,” currently available for streaming, the comedian journeys across the U.S. with his close friend Harper Steele, who came out as a transgender woman at the age of 61 in 2021. Their adventure includes a 16-day drive from New York to Los Angeles, during which they visit famous sites, enjoy alternative rock music, and munch on Pringles and McDonald’s coffee.

Whenever boredom struck, Ferrell humorously recounts how he would call any personal injury lawyer’s number featured on billboards. “We have hours of that footage—we had so much fun making ourselves laugh,” he says while enjoying a light lunch of salads and croissants.

How ‘SNL’ Ignited a 30-Year Friendship Between Will Ferrell and Harper Steele

The two have been friends since they started working together at “Saturday Night Live” in 1995—Ferrell as a cast member and Steele as a writer. They quickly found they shared similar personalities and comedic styles, often retreating to Steele’s office during busy writing nights to chat and listen to music.

“I might be a bit grumpy, but I’m pretty chill overall,” Steele mentions while sitting next to Ferrell on a couch. “Will has this gentle demeanor unless he needs to be more animated, which is probably why we clicked so well.”

After their time at “SNL,” they collaborated on various films, including “Casa de mi Padre” and “Eurovision Song Contest: The Story of Fire Saga,” until the COVID-19 pandemic hit. It was during this time that Steele came out to her family and friends via email. Knowing her love for greasy diners and worn-out bars across America, Ferrell proposed a road trip so she could revisit those same places, now living authentically as a woman.

Initially, Steele declined the idea of documenting the trip. “I’m not one for cameras at all,” she admits. However, after thinking it over a few months, she realized the significance this documentary could hold regarding politics and the current trans issues in America, especially with so many anti-trans bills being proposed. “There’s some value in that. Plus, every time I work with Will, it leads to interesting projects. This one felt challenging and out of my comfort zone,” she added.

Ferrell also had his reservations about this deeply personal film, given that Steele allowed him to ask any questions regarding her life as a transgender woman, her years spent hiding her identity, and her battles with feelings of self-worth and insecurity. They also ventured into conservative areas in the U.S. where transphobia is prevalent.

“I was worried about whether I was asking the right questions,” Ferrell, 57, recalls. “There was also the concern of having a potential confrontation out there. When people asked what we were filming, would I be prepared to defend my friend and explain our purpose? Those thoughts were constantly on my mind.”

Harper Steele Aims to Live Without Fear as a Trans Woman

Thanks in part to Ferrell’s fame, most of their encounters with strangers are positive and warm. Nevertheless, the film also sheds light on the discrimination Steele faces as a trans woman. One scene depicts her receiving hateful messages on social media after being seen courtside with Ferrell at a basketball game in Indianapolis. Another scene features a tense dinner at a Texas steakhouse where she’s misgendered and met with hostile stares from other customers.

“I want to be in those places because I don’t dislike them. I don’t want to feel fearful about them,” Steele shares. “I’m interested in attending basketball games in the heartland, and I believe I should be received well there. However, I can’t fully assess my welcome since my experience was alongside Will Ferrell. With Will Ferrell, you’re always greeted warmly, so that doesn’t provide an authentic trans experience.”

After filming, she ventured across the Midwest on her own without the cameras.

“I’ve found it to be easier,” Steele expresses. “Part of that is due to my confidence going into those situations now.” She also notes that people generally “are not inclined to be unkind right away. Most people seek to be compassionate, although they might vent their negative feelings when they’re alone at home.”

Will Ferrell and Harper Steele hope their Netflix documentary will make a positive impact

“Will & Harper” is anticipated to receive an Oscar nomination for best documentary by many experts. This film marks a new and exciting phase for Ferrell, who, together with producing partner Jessica Elbaum, has been instrumental in bringing women-focused films like “May December,” “The Menu,” and “Am I OK?” to life.

“We aim to use whatever influence we have to elevate voices that don’t receive as much attention as they deserve,” Ferrell shares. “That’s our mission, and it’s incredibly gratifying when these projects resonate with audiences.”

Ferrell has already received messages from friends expressing, “I didn’t really grasp what it means to be trans,” and now they feel better equipped to support others through their transitions. Steele also hopes the film will make a “positive difference in the queer community.” Now residing in LA, she is grateful for the “kindness” Ferrell has shown her as they meet more often. She reflects that if she had come out as trans years earlier, she might never have been hired on “SNL” or formed a friendship with him.

“Anyone who comes out later may have regrets, but you can choose how to deal with them,” Steele explains. “I prefer not to dwell on them; I choose to live without resentment.”