When Will Ferrell received an email from his longtime friend and former Saturday Night Live writer Harper Steele, announcing her transition, he was filled with questions and curiosity about what this change would mean for their friendship. Harper, who had kept her identity private for years, was ready to live authentically as a woman and reached out to Ferrell for support. The result? A 16-day road trip across the U.S., which has been captured in Netflix’s new documentary Will & Harper, directed by Josh Greenbaum.
In a candid interview with the BBC, Ferrell reveals that the journey was as much about showing his support for Harper as it was about learning. “It was kind of earth-shattering news to receive,” he admits. “Selfishly, I thought this could be a great opportunity to ask all these questions and give Harper the chance to educate me.”
Their road trip spanned from New York City to Santa Monica, with stops at bars, diners, and sports arenas — places Harper used to enjoy but wasn’t sure how welcome she would feel after transitioning. “Was I afraid of what I might find out there? Of course,” Harper acknowledges, though she notes her experience traveling with a famous friend and camera crew offers some protection not available to many trans individuals.
One of the more tense moments occurs when Harper walks into a bar in Oklahoma draped in pro-Trump and anti-Biden flags. Ferrell waits outside but joins her when the situation becomes uncomfortable. When a local refers to Harper as a man, she calmly corrects them, with Ferrell by her side. “I don’t know if the cameras made people behave better,” Ferrell reflects, “but it felt like once we started talking, the barriers melted away.”
Despite the moments of tension, the trip also had its share of laughter and lightheartedness, a trademark of Ferrell’s comedic style. Whether it was a 72oz steak challenge or dressing up as Sherlock Holmes, the pair infused humor into even the more serious discussions.
While Harper faced derogatory social media comments, she remains hopeful. “I believe people are kind,” she says. “Letting a person live their truth should be everyone’s goal.”
Ferrell’s support for Harper transcended their road trip, solidifying their bond while offering viewers a mix of comedy, deep conversation, and the celebration of an enduring friendship. And as for the burning question Ferrell had from the start: “Does she still drink rubbish beer?” Harper laughs, “I don’t know if it’s the oestrogen, but I do prefer wine now.”
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