Will Ferrell and Harper Steele’s friendship dates back to their time at the well-known comedy show, Saturday Night Live (SNL). Ferrell emerged as one of the breakout stars of the show, while Steele worked diligently as the head writer from 2004 to 2008. Their companionship extended beyond the studio, translating into several successful collaborations, such as the widely-acclaimed Eurovision Song Contest: The Story of Fire Saga, and frequent hangouts at games and dive bars.
In 2021, Steele came out as a transwoman. This monumental decision was fraught with the universal question, “Will I still be loved?” as Steele articulates in their documentary, Will & Harper. The documentary chronicles their 16-day road trip from New York to Los Angeles, aimed at not only coming out to America with a sense of security provided by Ferrell’s celebrity status but also strengthening and exploring the nature of their long-standing bond.
The journey began with the packing stage, marked by an evident shift in Steele’s approach. As a man, her luggage typically consisted of a few tee-shirts, jeans, and underwear. Now, she found herself struggling with decisions as simple as which shoes to pack. The road trip essentials included chairs, a cooler, and what Steele humorously calls “natty beer.” The duo’s expedition commenced from New York, making a notable stop at SNL studios to reconnect with former colleagues and friends, including the legendary Tina Fey.
Throughout their cross-country voyage, they encountered diverse individuals at various bars and gas stations, each contributing their unique stories to the journey. A particularly poignant encounter occurred at The Grand Canyon, where they met a therapist who confessed her inability to assist a patient, giving insight into the universal struggles of mental health care.
Additionally, they visited Steele’s family, her children, and her sister, prompting Ferrell to inquire about their feelings regarding Steele’s transition. Long car rides fostered deep conversations between Ferrell and Steele about personal topics such as dating, surgery, and the spectrum of emotions—both despair and joy—that accompany a gender transition.
Their documentary provides viewers with an intimate lens into Steele’s life, such as the origin of her name, which is tied to her mother’s schoolmate, Harper Lee.
. Steele also discusses how transitioning requires significant self-acceptance, which she finds difficult at times due to aspects like her “low male voice.” These conversations unveil the intricacies of Steele’s journey toward self-identity and acceptance.
The journey was not without its lighter moments. Ferrell’s insistence on visiting a Dunkin’ Donuts, impromptu laundromat visits when clean underwear was nearly exhausted, humorous debates about comedy (which Steele notably dislikes), jokes about Nordstrom Rack, and getting jackets for their beer cans — aptly named Dolores and Cornelius — provided a blend of humor and relatability.
However, their experience was not entirely rosy. They faced some unwelcoming encounters in Texas, underscoring the rough patches that accompany such a poignant journey. This blend of positive and challenging experiences mirrored the unpredictability of life itself. They indulged in karaoke with ‘I Got You Babe’ and experimented with riding unicycles in Harper’s hometown, fondly reminiscing about Steele’s junior high school days.
Despite the sincerity of the documentary, its essence was occasionally overshadowed by the constant awareness of it being filmed, which lent an element of artificiality to what was an otherwise deeply personal voyage.
The trip concluded with Ferrell and Steele sitting on a tranquil beach. Ferrell presented Steele with a gift, a symbolic memento of their transformative journey. Echoing the lines from their documentary’s theme song, “It takes 3,000 miles to get this close,” the poignant sentiment underscored the essence of their adventure.
Ferrell and Steele’s Will & Harper is more than just a road trip; it is a tapestry of self-discovery, friendship, and acceptance. It’s an exploration of identities—both personal and interpersonal. This heartfelt and humorous documentary is currently streaming on Netflix, offering audiences a glimpse into a profound journey that marries camaraderie with individual transformation.
