Will Ferrell and Harper Steele’s friendship goes back 30 years, to their mutual starts at Saturday Night Live in 1995. Over the next 13 years, Harper would rise to be the Emmy-winning head writer of SNL, while Will would go on to become one of the biggest comedy stars in the world. Their friendship never flagged, though in 2020, Will received an email from Harper, who he had known as Andrew, that she would be transitioning to live fully as herself, a woman called Harper. Will was supportive, but he had a lot of questions, and out of that comes Josh Greenbaum’s road trip documentary, Will & Harper.

 

Harper always loved road trips, particularly driving the back roads of America, drinking “sh-tty beer”, bathing at truck stops, and hanging out at dive bars. As a transwoman, though, she is no longer sure if the country she loves “loves her back”, and so she embarks on a road trip from New York to California with Will in tow. He can ask his questions, and with the protection of a camera crew and her distractingly famous friend, Harper can test the waters of Back Roads, USA, at a time when 2SLGBTQIA+ rights are under attack across the nation. 

 

Will & Harper is a precisely controlled environment choosing to stick, as much as possible, to the positives in Harper’s life—the support and love of her family and friends, the positive interactions with the strangers she encounters on the road. In an Oklahoma bar decorated with Confederate flags and Trump memorabilia, a young man accepts correction when he misgenders Harper, apologizes, and moves on. Two Native American men sing a song for Harper, the bar, despite its décor, is warm towards her…and Will Ferrell standing over her shoulder. At a stock car race, the kind of event Harper always enjoyed but is now nervous to attend, a local encourages her to go where she wants, as if everyone will echo the same sentiment…with a camera in their face.

The artificiality of the experiment is acknowledged. Will and Harper make plans on how and when Harper will call if she feels she needs Will to come in and distract people, taking attention off her. But even before that, the cameras are there, enough of a guarantee nothing too bad will happen in the moment. Indeed, at a steakhouse in Texas where Will makes a spectacle of himself, the crowd feels palpably hostile, yet in the moment, nothing happens. The hate and toxicity are all spewed online. There’s never a real acknowledgment that in the absence of celebrities and cameras, these interactions could have, probably would have, gone very differently in person. Harper says she wants to prove to herself she can still enjoy the places and things she did before, but I’m not sure she does, at least as depicted within the events of the documentary.

 

The best parts of the film are Will and Harper shooting the breeze, talking about nothing and doing dumb comedy bits. Early on, Will wonders if Harper’s transition means their friendship will be different, but it’s obvious that no, it’s not. Harper is Harper, and Will has always known Harper, even when she had another name. And therein is the real value of Will & Harper as a document of trans life in America in the early 2020s. Excerpts from Harper’s journals illustrate how emotionally and mentally damaging living in the wrong body was, compared to how freely she moves and conducts herself, even when nervous, after transitioning. She makes no bones about it—she is happier now, more settled in herself, despite her misgivings about America’s political situation and the kinds of places she can and can’t navigate anymore. 

And there are plenty of touching moments, such as Will breaking down when he realizes what he subjected Harper to in the Texas steakhouse, or when he realizes only after the fact that Indiana’s seemingly friendly governor is anti-queer and has signed anti-trans legislation. Will realizes he missed a moment to press a politician on their policies, to force someone who can smile and shake your hand to acknowledge their prejudices to your face. And there are wonderful moments of Harper enjoying life as she always wanted, acknowledging her apprehension even as she goes forward to do the things she’s always loved doing. 

 

Will & Harper is a compassionate film that chooses kindness and celebration over pain and trauma. Given Will Ferrell’s celebrity, though, and how effectively the attention of cameras puts everyone on their best behavior, it does mean that Will & Harper is an inherently compromised document of the trans experience in America. But as a celebration of friendship and queer life, it is full of warmth and pathos. It is above all Harper Steele in her own words. After decades telling other people’s stories, Harper Steele is finally telling her own, her way. 

Will & Harper will stream exclusively on Netflix from September 27, 2024.