Will Ferrell, the beloved Hollywood star, received an unexpected email from his longtime friend Harper Steele a few years ago, revealing that she would be transitioning to live as a woman. This revelation prompted a series of reflective questions for Ferrell about the future of their friendship and the changes it might entail.
Curious to explore the dynamics of their relationship following this news, Ferrell invited Steele on a groundbreaking road trip across the United States. Their journey—designed to foster understanding and offer support—saw them visiting bars, diners, and sports venues, familiar haunts for Steele that now felt uncertain.
The duo’s 16-day adventure from New York City to Santa Monica, California, serves as the centerpiece of a new documentary titled Will & Harper, shedding light on their friendship amid personal transformation. Ferrell noted that learning how to support Steele became crucial for him, especially after she requested him to “stand up for me.”
“Receiving that news felt earth-shattering, but I didn’t want our friendship to change,” Ferrell explained, admitting his intentions to deepen their connection through this journey.
Ferrell and Steele’s friendship began when they were both cast members on Saturday Night Live in 1995. Steele went on to become a chief writer and was instrumental in supporting Ferrell’s career during his early days on the show.
Steele remarked, “This support as a trans woman goes far beyond what I ever gave him.” The road trip marks her first major journey since transitioning, bringing excitement and some apprehension about being in public as her authentic self.
Semi-awkward moments surfaced during their travels, particularly when Steele entered a local bar in Oklahoma, where the atmosphere felt potentially unwelcoming. With Ferrell by her side for support, Steele confidently confronted mistaken perceptions about her identity, illustrating the complexities of social interaction around acceptance and understanding.
Both Ferrell and Steele acknowledged that while their celebrity presence might offer some level of protection, true conversations can often blossom when the initial curiosity subsides.
During their travels, the comedic essence of Ferrell was evident when he dressed as Sherlock Holmes to take on a massive steak challenge at a Texas steakhouse. The spontaneous act drew a crowd, but it also led to uncomfortable moments as social media comments regarding Steele’s transition flashed onscreen, prompting genuine reflection from both friends.
Steele expressed the emotional toll of receiving negative commentary, stating, “When you’re trans, you ingest a lot of that rubbish. Those tweets linger.” This candid moment added depth to their lighthearted adventure, bridging both humor and seriousness throughout their journey.
Steele remains acutely aware of the societal debates surrounding gender identity, sharing her insights on the politicization of trans issues. “I believe people are kind, and everyone should have the freedom to live their truth,” she asserted, emphasizing the importance of acceptance and understanding in a polarized environment.
While the documentary includes poignant discussions, it also captures the lighter side of their adventures, showcasing the duo’s innate humor. “Even during emotional moments, they weave humor into their conversations,” the director noted, highlighting the balance of comedy and candidness that defines their friendship.
So, does Steele still favor her “rubbish beer?” In a light-hearted twist, she quipped, “I think it might be the estrogen, but I do prefer wine now!”
