When former Saturday Night Live writer Harper Still came out as a convert to her decades-long boyfriend Will Ferrell, the couple decided to take a road trip from New York to Los Angeles.
We all feel like we know Will Ferrell by this point. He’s a funny, loud guy and will do anything to get a laugh. He has many leather-bound books and his apartment smells of rich mahogany. He is the Burgundy Rune, Lord Business, Mugatu. Much of that character is still here in this fascinating documentary, but toned down. The focus is instead on his longtime friendship with former SNL writer Harper Steele, who came out as transgender in 2021.
Steele’s unexpected emergence, which occurred late in life, is explained in a startling prologue, in which Ferrell reads the email Steele sent him: tough, open, honest, funny (“Instead of being a fool, I’d be a whore”). It sets the tone for the entire movie. The two friends decide to take a road trip across America to process it all, based on Steele’s love of moving across the country, and use that as an opportunity to recast the friendship in its new guise. It is an internal journey taken on an external journey.
Ferrell inevitably finds moments of bizarre silliness, but he’s also tender and generous.
Director Josh Greenbaum is best known for Barb And Star Go To Vista Del Mar, but there’s little of the silliness or surrealism of this film here: it’s much more honest and profound. Ferrell, inevitably, finds the occasional moment of grotesque silliness — he throws a mock tantrum when they don’t stop for cake, and dresses up as Sherlock Holmes during dinner at a restaurant — but he’s also tender and generous toward his friend, who is still navigating a new, sometimes painful, and empowering new life in Sometimes.
It’s especially poignant during their visits to less tolerant parts of the country, and there are times when the film gets really tense: especially when the pair visit a Texas steakhouse and have an awkward encounter with Indiana Governor Eric Holcomb, who shows up later. I passed anti-trans laws. Ferrell is sometimes naive to the dangers, but he is also very supportive of his friend, his immense fame acting as a shield and magnet for unwanted attention. But his participation in this film is commendable. At a time when many millionaire comedians are using their large platform and power to demonize a minority, it’s very refreshing to see someone try a different approach.
The film acts as a kind of learning experience – for Ferrell, who is trying to understand the new dimension his friendship has taken; For Steele, who is still grappling with her identity and how others receive her; And on our part, the audience, at a time when the “debate” about transgender people still seems so ugly and ill-intentioned. “The biggest question people ask when they come out of the closet is: Will I still be loved?” Steele says at one point. This film is a definite and honest answer to that question.
An affectionate film of road trip friends, featuring unseen depth from Will Ferrell, this documentary is illuminating, timely, and gently funny.
