Trans Friend Will Ferrell Travels Across the Country

Former “SNL” castmates travel from coast to coast in a sweet film rooted in friendship.

Adam Graham
| Detroit News Film Critic

Will Ferrell travels across America with his best friend in “Will & Harper,” a gentle and caring documentary about truth, discovery and the open road of friendship.

Harper Steele is her co-pilot for the adventure, and she’s following her own path: The former “SNL” writer underwent a gender transition during the COVID-19 pandemic, announcing her intention to Ferrell and a few close friends and family members via email. Harper had plenty of questions of her own — “Will I still be loved?” and “What do we do from here?” among them — and she knew Ferrell would have his own questions about his transition, so the couple packed a car and hit the road, traveling from New York to Los Angeles in 16 days with a film crew in tow.

There are a few stops along the way, first at the “SNL” studios and for dinner with familiar faces like Colin Jost, Tim Meadows, Seth Meyers and Tina Fey. There are a few of those meet-ups with former “SNL” stars built into the trip, which seem mostly designed for the audience watching at home.

But the heart of the film is the relationship between Will and Harper, which hasn’t changed, but now has a different dynamic. They’re clearly comfortable with each other, and Harper lets Will ask her whatever questions he wants, and he leans in to ask her about her new breasts.

But there are much deeper, richer conversations about Harper’s self-discovery and her long journey toward transition, and the feelings she’s always had about her place in the world. The road trip is a part of her life: Throughout her life, one of her favorite things to do has been to travel the country and hide out in dumps and speakeasies in the middle of the country, and she wonders if she can still do those same things, in the same way, now that she’s a woman. Would it be the same? Does she face new threats?

Ferrell is both a help and a hindrance in these circumstances. He’s sort of like a jack of all trades, in that he can go anywhere in this country and be recognized and receive love and laughter from strangers. He helps Harper out of some social troubles, but he also attracts the wrong kind of attention when the couple visits a Texas barbecue restaurant and he dons a Sherlock Holmes costume and she unwittingly becomes part of his sideshow.

It’s a learning moment for the couple, and the trip is full of them, as they pull out their camp chairs and crack open a few beers in parking lots, along the road, and at the beach. And they talk, like old friends talk, and they share laughter and jokes and tender moments together during that most classic of American rituals, the road trip.

“Will & Harper” is a bit contrived at times (there’s a Kristen Wiig segment that has a nice ending, even if it feels stretched out for narrative purposes), but if those gags help draw attention to a story that deserves to be seen by as wide an audience as possible, then so be it. This destination is well worth the journey.