The road movie is a quintessential part of American cinema. Some would argue that Will Ferrell is a quintessential part of American comedy. Until recently, trans stories have not been a quintessential part of mainstream media, often ignored or reserved for subculture-like spaces. Ironically, all three topics combine in Josh Greenbaum’s latest film and fourth documentary feature, Will & Harper.
Will Ferrell first met Harper Steele back in the 1990s on Saturday Night Live. The latter was hired as a writer, while the former was placed in the cast. Ferrell’s appreciation for Steele is felt early on in the film when he remarks that many of the writers didn’t know what to do with him. He credits much of his career decisions to Steele, from to his stint in a Lifetime movie to the Spanish-speaking Western Casa De Mi Padre.
Early in its runtime, Ferrell details the email Steele sent him where she reveals that she is a transwoman. Steele, who appears onscreen soon after still feels apprehensive about where their friendship will go from here and explains that the one thing she will miss about her life pretransition would be road-tripping and visiting the underbelly of America.
Will quickly suggests that they take the trip together traveling to various parts of the country, from attending an Indiana Pacers game, to visiting Harper’s childhood home, to hot air-ballooning in Albuquerque with Will Forte. It’s through those experiences that the pair not only become closer together but where Farrell experiences the fears and hardships Harper could experience the rest of her life.
Director Josh Greenbaum is no stranger to the comedic documentary. There’s one scene in Too Funny To Fail, a doc about Dana Carvey’s failed TV show that still makes me dissolve into laughter. In his past work, Greenbaum used mainly talking head interviews where he would step in with the occasional question, reenactment, or archival footage. In Will & Harper, he lets them take the lead the entire time, relying on these showbiz professionals to lead the way. The one thing that took away from the experience was the constant needle drops which detracted from the story.
Though parts are clearly planned out and orchestrated, Greenbaum leaves room for both people to be themselves. Ferrell shows up in costume numerous times and isn’t afraid to perform bits for the camera. Steele may be quieter than her friend, but she is even more open, asking hard questions and sharing her fears about frequenting the seedy bars and greasy diners she used to go to before she transitioned.
Ferrell and Steele are a dynamic cinematic duo. The former SNL cast member knows when to perform for the camera and when to let Harper have her moment. Without trying, Ferrell models how to be an ally and that includes making mistakes. He regrets not educating himself on Indiana Eric Holcomb’s support of banning gender-affirming before meeting him. He breaks down in Texas after a bit he does draw attention to the duo and vile comments about Harper’s existence show up on the internet.
Don’t get me wrong, Will & Harper is hilarious. While the film is an exploration of friendship and allyship first, it feels like a masterclass in comedy. They meet up with several of their colleagues including Tina Fey, Seth Meyers, Colin Jost, Paua Pell, Tim Meadows, Molly Shannon, and the aforementioned Forte.
In some flyover state, Kristen Wiig, who was a part of that Lifetime movie and worked with Greenbaum on the underrated Barb and Starr Go To Vista Del Mar, is asked by the duo to write a theme song for their trip. The pair have a lot of demands, needing it to be funny but also bring a tear to the eye and somehow both jazzy and country at the same time. Ferrell and Steele check in with her throughout the film with no response, however, we do get a delightful little number during the credits that starts along the lines of “Harper and Will go west. Just two old friends and a new pair of breasts.”
Will & Harper is probably the most important film Ferrell will ever make. We don’t often see depictions of older people transitioning and being so vulnerable about their journey. Even more than that, the film smartly capitalizes on Ferrell’s persona. Known for his often bro-y and sophomoric fare, he and his team have made something that transpeople of all ages can not only relate to but watch with those in their lives who might not yet be allies but call themselves Ferrell fans. This film will build connections, start conversations, induce laughing fits, and even save lives along the way.