Will & Harper

Comedian Will Ferrell goes on a cross-country road trip with longtime pal Harper Steele after she transitions in a movie that's a hilarious and tender portrait of an evolving friendship.

Friendships change over time, in no small part because people change — usually slowly and subtly, but sometimes suddenly and dramatically. Comedian Will Ferrell and TV writer Harper Steele saw this when the latter transitioned at the age of 60. They got to know each other while working on “Saturday Night Live” decades ago, and just clicked.

Now that Harper (who used to go by Andrew) is living as a woman, Will proposed they take a 16-day road trip together across the U.S. The topline notion is to help Harper, a lifelong wanderer, reacquaint herself and see if she’s still comfortable with her favored pastime of dropping into greasy diners and shady roadside bars. And it gives the two of them a chance to assess their relationship and see how this change will impact it.

“Instead of an asshole, I'll be a bitch,” Harper jokes about her curmudgeonly ways.

“Will & Harper” is the movie chronicling that journey — part documentary, part therapy, part comedy.

Directed by Josh Greenbaum (“Barb and Star Go to Vista Del Mar”), it’s an often hilarious but also tender portrait of an evolving friendship, as well as a snapshot of America and its attitudes toward trans people. There will be moments of absolute cruelty, but also uplifting embrace.

The Netflix film opens in theaters this week, and debuts on the streaming platform Sept. 27.

Probably the key moment in the movie is when they arrive at a seedy bar in Oklahoma. Harper, who is starting to feel a little more comfortable in this new identity, asks Will to stay outside while she goes in alone. After some lonely moments of uncertainty, she finds herself chatting amiably with the locals, and eventually Will comes in and things light up.

Of course, their ongoing experiment in seeing how people will react to Harper, and she to them, is affected greatly by the presence of a highly recognizable movie star. When the go into a public setting, all the attention is on Will, who then introduces Harper to everyone and acts as a bit of a shield.

Not all encounters go so smoothly. A stop in a famous Texas steakhouse to take on the challenge of downing a 72-oz slab of beef results in some very nasty tweets and public reaction. Watching Harper read these aloud to Will the next day is just heartbreaking.

They also have an ongoing conversation about their roles as a comedic performer and writer. Will acknowledges his instinct is to always be “on” in public spaces and go for the laugh, and worries this exposes Harper to ridicule. (His wearing a Sherlock Holmes costume at the steakhouse probably didn’t help.) We also learn that a guy famous for flaunting his flubbery physique for laughs has body issues, just like most of us.

Their stop in Indiana comes early in the trip, including buying a veritable trove of Pringles chips at a Beech Grove Wal-Mart and then having an impromptu camp-out in the parking lot.

They also attend a Pacers game, about which I recall there being a large amount of media coverage back in spring of 2023. Will revved an Indy Car engine and pumped up the crowd over the PA system. In a telling moment, he began to introduce Harper and announce her transition, but the audio had already been cut off to return to the game.

They also had a dialogue with Gov. Eric Holcomb, without Harper knowing who he was at the time. Later they learn Holcomb is one of a number of state leaders to sign legislation limiting the ability of minors to transition. Will blames himself for not confronting Holcomb and defending his friend.

Cruising around in Harper’s vintage Jeep Cherokee outfitted with cameras and followed by a film car, “Will & Harper” is filled with gorgeous backdrops from across America that are sure to stir the heart. But it’s at its most profound during the small, quiet moments when Harper talks about what it was like for her to live so much of life feeling disconnected from her own body and identity, despite following a traditional path of career, marriage and kids.

“My whole writing career, my whole creative life, I performed as a character named Andrew.”

She chose the name Harper because her mother was a schoolmate of “To Kill a Mockingbird” author Harper Lee. She loved riding a unicycle all around her hometown of Iowa City, and gets a chance to refresh those skills. We also learn she had been ‘practicing’ living as a woman for years, even buying ramshackle house in Trona, Calif., just so she could have someplace to walk around wearing dresses.

Harper laments her (her words) masculine face and deep voice. She and Will joke about the gloriousness of boobs. And if she’s a worse driver now that she’s a woman. Harper invites her friend to ask questions about things like bottom surgery and seeking a relationship post-transition; he does, and she answers honestly and earnestly.

Harper admits to suicidal thoughts, struggling with passing as a woman and being misgendered, as when a diner waitress calls her “sir” while taking their order.

“I'm not afraid of people; I'm afraid of hating myself,” she says.

A number of famous friends and SNL alums appear, including Tim Meadows, Tina Fey, Seth Meyers and more. Molly Shannon joins them for a three-way pedicure. Will Forte takes them up in a hot air balloon. They jokingly ask Kristen Wiig to come up with a theme song for their trip, and then leave voice messages pestering her about why she hasn’t come through.

(Stick around for the credits to finally hear it — it’s actually a really amazing song.)

Life can be strange and uncomfortable. Knowing someone for decades as a guy and then they become a gal probably results in a lot of friendships that sputter and falter. “Will & Harper” is a story about two people who decided to step on the gas instead, and see what lies over the horizon.