Will Ferrell hits the road with an old new friend in ‘Will & Harper’
“Will & Harper” — 3 stars
A road trip across the United States turns into a testament to self-acceptance and allyship in the tender, heartfelt documentary “Will & Harper,” in which Will Ferrell and longtime pal Harper Steele, who has recently come out as trans, embark on a cross-country quest in a wood-paneled Jeep to reacquaint Steele with the America she loves.
The comedy star and writer, respectively, first met three decades ago working on “Saturday Night Live,” where they found in each other simpatico comedy soul mates. When filming begins in 2023, Steele, 61, has undergone gender transition during the pandemic, confiding in friends and family her fears and self-doubt, as well as her optimism for the future.
How the world will embrace her weighs heavily on Steele. Traversing America’s roadside diners and dive bars to chat up locals is the kind of trip she loved to take solo but is now nervous to attempt amid widespread transphobia and anti-trans legislation. (In 2023, a record 510 anti-trans state bills were introduced, per the ACLU.) “I love this country so much,” she says. “I don’t know if it loves me back right now.”
So when a supportive Ferrell proposes a 17-day ramble from New York to California to bond and visit Steele’s old haunts, the aim is one of mutual discovery: They’ll ask each other the hard questions as the next chapter of their friendship evolves, and the “Anchorman” and “Talladega Nights” star will act as buffer-slash-wingman to help his friend negotiate spaces that no longer feel so welcoming.
Directed by Josh Greenbaum (“Barb and Star Go to Vista Del Mar”), the journey begins with a send-off from Tina Fey, Seth Meyers and other famous friends, but it doesn’t need the flourishes that lend a sheen of mainstream-appeal premeditation. (Cameos from Will Forte and Molly Shannon, however, are sweet sojourns in their quest, while a delightful theme ditty cowritten and performed by Kristen Wiig could put “Will & Harper” in the running for the best original song Oscar.) Ferrell’s candid curiosity about Steele’s transition, and her own poignant confessions, keep the film motoring along in the safety of their nearly 30-year friendship as a small crew trails them and car-mounted cameras film discreetly, like flies on the windshield.
And the jokes never stop as the two old friends riff their way through pit stops from Washington, D.C., to Las Vegas, where Ferrell dons a ridiculous disguise for a night on the town. Their chemistry is so affectionate and affirming, it’s a joy to watch the pair scarfing Pringles in a Walmart parking lot, arguing the finer points of cheap beer, or cannonballing into their motel pool, and “Will & Harper” rings most true when it ditches the gimmicks and sticks to the comedians in (and out of) cars, getting real.
Touching exchanges unfold between Steele and her children and sister, with a fellow trans woman in Peoria, among strangers at an Oklahoma biker bar adorned in Trump and Confederate flags, and even at the Grand Canyon. The positive interactions may upend viewer expectations. They even take Steele by surprise. “I’m not really afraid of these people,” she realizes after receiving encouragement at a rural auto racetrack. “I’m afraid of hating myself.”
While she acknowledges the privilege her friend’s fame affords her on this trek, the spotlight also places her in several distressing situations. She is repeatedly misgendered by strangers and is introduced to Indiana Gov. Eric Holcomb while she and Ferrell sit courtside at a Pacers game, only to later learn of his support for anti-trans legislation. Both become visibly uncomfortable at a Texas steakhouse where Steele and Ferrell, who is dressed inexplicably as Sherlock Holmes, are met with frosty stares in the room and transphobic comments online, but only Ferrell seems shocked that the stunt backfired.
It’s one of many sobering moments the two share as they unpack their experiences, along with gutting revelations of pain and self-hatred Steele shares when they reach the Mojave Desert. At times a case study in How to Be an Ally, the film is accessible by intention. Yet it remains raw, vulnerable and joyful, even when things get messy, as it charts a road map to empathy and acceptance — the real destination that awaits at the end of their cross-country odyssey.
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At Wayfarer Theaters in Highland Park and Landmark Century Centre Cinema in Chicago. Available Friday, Sept. 27, on Netflix. Rated R for strong language. 114 minutes.