Will Ferrell and Harper Steele first crossed paths during their days at the iconic comedy show, Saturday Night Live (SNL). Ferrell had emerged as one of the breakout stars, leaving audiences in stitches with his memorable sketches. Steele, on the other hand, wielded her creative prowess behind the scenes as the head writer from 2004 to 2008. Despite occupying different realms of the show, the duo forged a close friendship that has stood the test of time, strengthened through collaborations on projects like the well-received Eurovision Song Contest: The Story of Fire Saga.
The world saw a new chapter unfold in Steele’s life when she came out as a transwoman in 2021. Navigating the complexities of this significant revelation, she articulated a concern that resonates with many in the LGBTQ+ community: “The biggest question when people come out of the closet is, ‘Will I still be loved’.” This poignant introspection sets the stage for their latest venture, Will & Harper, a documentary that chronicles their road trip across America from New York to Los Angeles.
Setting out on this sprawling journey not only serves as Steele’s symbolic coming out to America but also as an opportunity to re-examine and deepen the bond between Ferrell and Steele. The packing for the trip itself highlights changes in Steele’s life. Once content with packing just some tee-shirts, a pair of jeans, and underwear, she now finds herself deliberating over which shoes to bring. Amidst this seemingly trivial dilemma, the underlying message is profound—every aspect of her identity is now part of her meticulous self-expression.
Equipped with the essentials for a traditional American road trip–chairs, a cooler, and, as Steele humorously notes, “a natty beer”—the friends depart from New York. Their first significant stop is at the SNL studios, a place filled with nostalgia and camaraderie. Here, they reunite with former colleagues and friends including comedy stalwart Tina Fey, rekindling memories and reflecting on past shared laughs.
Over the course of 16 days, Ferrell and Steele traverse the vast American landscape, making brief, yet impactful, connections with strangers they meet at bars and gas stations. A particularly moving encounter occurs at The Grand Canyon, where they meet a therapist grappling with the personal despair of not being able to help a patient. Such encounters enrich the narrative, offering glimpses into the lives of everyday Americans, adding layers of authenticity to their journey.
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The documentary also provides intimate glimpses into Steele’s personal life. Ferrell meets Steele’s children and her sister, seeking their sentiments and support concerning Steele’s transition. The long hours spent driving allow Ferrell to engage Steele in meaningful conversations about her experiences with dating, surgery, and the oscillating emotions of joy and despair. This open dialogue is both heartwarming and revealing, showcasing the depth of their friendship.
Amidst the serious discussions, the trip is sprinkled with moments of levity. Ferrell’s insistence on visiting a Dunkin’ Donuts and their last-minute laundry run due to a shortage of clean underwear add a touch of humor. Their playful banter includes Steele’s distaste for analyzing comedy, a joke involving Nordstrom Rack, and acquiring beverage jackets for their beer cans affectionately named Dolores and Cornelius. These quirky moments offer a delightful counterbalance to the more intense parts of their journey.
While the duo is largely met with kindness and acceptance, their experience in Texas stands out as a sobering reminder that prejudice still exists. Despite this setback, they power through with resilience, engaging in light-hearted activities such as karaoke to Sonny and Cher’s ‘I Got You Babe’ and attempting to ride a unicycle in Steele’s hometown, reminiscent of her Junior High days.
As their journey nears its end, the documentary subtly touches on the inherent artifice of filming a deeply personal narrative. Despite the presence of the camera, Ferrell and Steele’s authenticity shines through, offering viewers a genuine glimpse into their profound and evolving bond.
The culmination of their trip is marked by a serene moment on the beach. Ferrell presents Steele with a heartfelt gift—a small, yet meaningful, memento encapsulating their transformative journey. As the credits roll, lines from the theme song ‘Harper and Will Go West,’ written by Kristen Wiig, echo the sentiment of their adventure: “It takes 3,000 miles to get this close.”
Will & Harper, available for streaming on Netflix, is more than just a documentary; it’s a celebration of friendship, acceptance, and the arduous, yet rewarding, journey of self-discovery.
