As excursions with a pair of comedians tend to go, Will & Harper is filled with those kinds of friendly jabs and jokes. Near the beginning of their trip, Steele unironically purchases numerous cans of flavored Pringles before the pair sets up folding chairs in the middle of a Wal-Mart parking lot to eat them. Their transportable furniture becomes a running gag, in which they plop down in random places to enjoy the beauty of their ordinary and extraordinary views. Along the way, Ferrell whines when Steele refuses to stop at Dunkin’ Donuts, disguises himself in a ludicrous getup for a fancy Las Vegas dinner, and yells angrily at barking dogs from the perch of a hot-air balloon. Though his humor sometimes masks some awkward moments, it’s more often a safety valve and resource when the mood dips or the tension spikes.
Greenbaum, who recently directed the comedies Barb and Star Go to Vista Del Mar and Strays, has a good sense of rhythm and pacing, knowing when to let Ferrell and Steele get vulnerable with each other. To their credit, the conversations never feel too forced, and the more they open up, the more both friends ease into their redefined relationship. Though Steele had known her transition was a long time coming, it was frequently interrupted by therapists uninterested in guiding her to embrace that kind of change, she says. It leads Ferrell to ask about breast surgery, and whether she’s struggled with body dysmorphia. “Every time I’ve done something for myself, it’s been guns blazing,” Steele says. Another day, she remembers the depressive thoughts that made her scared to keep a gun in the house. After her transition, though, “all I wanted to do was live,” she says.
Will & Harper doesn’t dive too deeply into politics. The closest it comes is during a Pacers game, where Ferrell and Steele sit courtside and briefly speak with Indiana’s governor. The next day, they realize that he—like many other state leaders—had recently signed a statewide gender-affirming care ban, and Ferell laments not pressing him about it. Still, if it feels like the road trip has too many sanded edges, or that it’s painting too palatable a picture of strangers accepting Steele in various social settings, the pair do encounter adversity during a pit stop at a Texas steakhouse. When Ferrell walks in, ready to devour an enormous steak while dressed as Sherlock Holmes, he’s greeted by hordes of gawking restaurant-goers recording him and Steele with their phones. The next day, Steele reads through a host of vicious and transphobic social media posts, prompting Ferrell to get emotional. “I feel like I let you down at that moment,” he says through tears.
It’s one of the few times that Ferrell’s celebrity doesn’t shield Steele from online and verbal attacks. The documentary is aware that the presence of a celebrity companion doesn’t always make for an honest representation of the treatment directed toward transgender people. But Ferrell’s presence is just as easily an example of how important allyship can be. At a diner, he gently corrects a waitress addressing Steele as “sir.” And when Steele wants to enter a seedy Oklahoma dive bar—plastered with Trump and confederate flags—by herself, Ferrell waits in the parking lot, waiting to spring inside if necessary.
There’s nothing too inventive about Greenbaum’s structure and aesthetic. While his subjects drive over highways and dirt roads, he supplements his footage with lighthearted montages and mainstream needle drops—he samples Brenton Wood, Bob Dylan, Tom Petty, and Frank Sinatra—and even sources an end-credits original from Kristen Wiig. Everything feels a bit conventional and accessible—which is the whole point. A road-trip documentary like this is really just the starting point of a much longer journey of understanding and acceptance. It’s an icebreaker—for its subjects, and for everyone watching. As the pair of friends depart from the California coastline, Ferrell acknowledges that once the cameras stop rolling he’ll probably have even more questions for Steele. “I’m going to think of something to ask you tomorrow,” he says. Then he takes a beat. “But we have time.”