Will and Harper - Stream It or Skip It

For Will & Harper, this is a trip into what it means to transition in modern America: the long journey to self-acceptance, the polarising and damaging effects of toxic social media, and the importance and beauty of friendship and love in setting people free. The result is a tender, funny, emotional and urgent journey across a country where trans people are routinely persecuted, silenced and targeted. Will and Harper is streaming now on Netflix.

Will Ferrell and Harper Steele worked together on Saturday Night Live in the 1990s. Will was an eager young performer looking to break into the comedy mainstream, and Harper was a writer who brought out the best in Will’s comedic power week after week.

During the height of the pandemic, Harper came out to Will as transgender in a letter, where she stated, “I’m old now, and as ridiculous and unnecessary as it may seem to report, I’ll be transitioning to live as a woman.” For a few brief minutes, Will wasn’t quite sure what his response should be; after all, what do you say to a friend of so many long years who shares something about themselves, long hidden, that is so brave, direct and important that it changes their world and yours. Like any good friend, Will knew the only response was to support, encourage and thank Harper for telling him. But he also had questions, so many questions, and what better way to get those questions out than by embarking on a road trip across America?

For Harper, an Iowa-born, adventurous, and lovable writer who hid their discomfort and uncertainty behind a man’s man image, the road trip is an opportunity to explore the trans experience in many of the small-town bars and diners they once frequented. At the same time, for Will, it’s a chance to get to know his new, old best friend again.

Director Josh Greenbaum places Harper’s story centre stage while allowing Will to explore many of the questions he kept inside following the letter, creating a road trip buddy movie where learning, sharing, and honesty sit at the heart of the conversations, laughter and tears. However, while sincere and enjoyable, one question remains as the credits roll: do Will & Harper offer us any genuine insight into the experiences of trans people in a fragmented and divided United States? Here, Ferrell’s ability to captivate an audience and entertain raises doubts about whether Harper’s experiences alongside him accurately reflect the true levels of discrimination and oppression faced in many American villages, towns, and cities.

Both Will & Harper acknowledge this during the trip and attempt to explore attitudes away from Will’s celebrity, including those of the keyboard warriors who hide behind social media as they spread their hate and bile. Still, one can’t help but wonder if many trans people watching while appreciating Harper’s honesty and bravery will feel the documentary doesn’t go far enough in uncovering the modern-day experience of many trans- Americans.