TIFF 2024: ‘Will & Harper’: It’s About the Journey AND The Destination

There is a moment during Josh Greenbaum’s winning, beautiful documentary, Will & Harper, when Harper Steele looks at pictures of herself while visiting the town where she grew up. She stares wistfully at a black-and-white photo of a child version of herself, her hair long and her eyes contemplating mischief. As she stares at her young self, we can see how much she would say to her, if she was given a chance. Greenbaum’s film is a tribute to allyship and enduring love, but, most importantly, it’s about connection through conversation.

Harper Steele has a very famous friend named Will Ferrell–you may have heard of him? The pair met when Ferrell was cast on Saturday Night Live in 1995, and the other writers weren’t sure what to make of this gung-ho, silly, curly-haired man. Steele (then known as Andrew) saw something in him and assured them that he would find his place. After decades of basketball games and debating the qualities of various beers, Steele surprised Ferrell when she sent an email announcing her transition. Ferrell admits to having a lot of questions, but who wouldn’t? “Will I be making a new friend,” he ponders.

Steele and Ferrell pile into Steele’s car when they decide to travel across the country to get to know each other all over again. When you are trapped in car with someone, you have literally all the time in the world, and this two-week trek allows these life-long friends to speak candidly about things like Steele’s selection of her new name as she tries to re-adjust her life to going to dive bars and Pacers games in her authentic skin. She never shies from telling people about her personal journey even though we know that she is nervous to. In one sequence, Ferrell stays in the car while she grabs a drink in a small bar decorated with proud Confederate flags and Let’s Go Brandon décor. It leads to a deeply emotional, surprising set of conversations that the audience may not expect.

Ferrell is associated with so many dorm-room-friendly posters of bro-y films, but you will never look at him the same way again. He could make anyone chuckle but seeing him in his own skin is so rewarding. His love for Harper is so genuine and so strong, and he is afraid of making mistakes because of this affection that has not waned for three decades. There are two separate dinner conversations where Will and Harper sit across the table from one another, and Ferrell reflects what it’s like for people to look inside that fishbowl. It’s entirely different when that fishbowl includes a more vulnerable person.

Harper Steele lives in a country that doesn’t always love her back, and Greenbaum’s film does shows how people on their journey react to Harper’s presence. I was honestly a little afraid that the film would lean too heavily on the world of entertainment or the other famous faces (like Paula Pell, Kristen Wiig, and Seth Meyers) would detract from the message of the film. It only enhances how deeply Harper is loved. Greenbaum’s film stealthily hits our empathy buttons for audiences who might not fully understand the inner conflicts of a transgender person and the director wraps it into a heartfelt, genuinely hilarious film about our collective ability to accept and love. You wouldn’t close the door on the face of a friend, and Will & Harper is such a marvelous film.

Will & Harper will debut on Netflix on September 27