A random collection of films authored by or about my transgender, intersex sisters, and gender-nonconforming persons all over the world. I watched some of them, and I was inspired by some of them. I met some of the authors and heroines, some of them are my best friends, and I had the pleasure and honor of interviewing some of them. If you know of any transgender documentary that I have not covered yet, please let me know.

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Will & Harper

Director: Josh Greenbaum
Release Year: 2024

Synopsis:
"Will & Harper" is an emotionally resonant documentary that transcends the boundaries of traditional road-trip films. Directed by Josh Greenbaum, this 2024 American documentary follows the journey of comedian Will Ferrell and his longtime friend, writer Harper Steele, as they embark on a 17-day road trip across the United States. What makes this documentary especially powerful is that it captures not just a physical journey across America, but an emotional one as Harper navigates the process of gender transition. The film is both a personal and poignant exploration of identity, friendship, and the ways in which life’s most significant changes can reshape relationships and perceptions. 
 
Will Ferrell and Harper Steele’s friendship dates back nearly three decades, beginning when they met on the set of "Saturday Night Live" (SNL) in 1995. They shared a creative partnership that grew over the years, culminating in their work together on films like "Eurovision Song Contest: The Story of Fire Saga". But in 2021, during the height of the COVID-19 pandemic, Ferrell received a deeply personal message from Harper—she was coming out as a trans woman. This revelation marked the beginning of an important new chapter in their relationship, one that would soon become the subject of a heartfelt documentary. The idea for the film arose as both Ferrell and Steele realized that their friendship, which had been built over many years of creative collaboration, needed to evolve in the wake of Harper’s transition. The two decided to hit the open road together for a 17-day journey across America, documenting their experiences, their reflections on their friendship, and Harper’s reintroduction to the world—this time as her authentic self. Through laughter, tears, and candid moments, "Will & Harper" is a testament to how love and friendship can endure and even thrive when faced with profound personal change. 
 
The documentary begins in New York City, where the pair pays a visit to the iconic "Saturday Night Live" Studio 8H, which holds special significance in both of their careers. It’s here that they meet up with old friends from the SNL family, including Tina Fey, Colin Jost, Paula Pell, and Tim Meadows. The reunion is emotional, filled with laughter, warmth, and the shared bond of a long history. But it’s also here that Tim Meadows recalls an email from Harper, revealing her transition, which he initially thought was a joke—a telling moment that highlights the often unpredictable and humorous nature of their friendship. From there, the road trip takes them to various American cities, each with its own set of challenges and poignant encounters. In Washington, D.C., they confront the political landscape surrounding trans rights, while in Beech Grove, Indiana, they attend an Indiana Pacers game, where they inadvertently find themselves at the center of a larger political and social discussion after the passing of a bill banning gender-affirming care for minors in Indiana. The documentary also brings attention to the broader political climate of the 2020s, marked by increasing anti-LGBTQ+ rhetoric and legislation in many parts of the United States. In Peoria, Illinois, they meet Dana, another woman who transitioned later in life, much like Harper. Dana’s story offers a deeply human perspective on the struggles and triumphs of transitioning, including the challenges of reconciling one’s internal sense of gender with how the outside world perceives them.
 
The journey continues to Meeker, Oklahoma, and Amarillo, Texas, where the film captures a particularly uncomfortable moment. At a steakhouse, the social media comments about Harper’s presence are filled with misgendering, profanities, and prejudice—an unwelcome reminder of the hate that many trans people face in public spaces. Will Ferrell, dressed in a Sherlock Holmes costume to amuse the audience, inadvertently draws attention to Harper’s identity, a situation that causes tension between the two. Ferrell, who initially failed to understand the gravity of the moment, later reflects on the experience as an example of the transphobia that Harper endures on a daily basis. Throughout the film, the camera captures not just the discomfort and challenges Harper faces, but also the deep bond between her and Ferrell. As the two of them drive from one city to another, they reflect on their friendship, the ways in which their relationship has changed, and the larger cultural shifts happening around them. The journey becomes not only a personal one for Harper but also a moment of growth and understanding for Will Ferrell, who, despite his fame and often comedic persona, begins to see the world through a more empathetic and nuanced lens. 
 
At its core, "Will & Harper" is a tribute to the enduring power of friendship. The documentary is deeply personal, showcasing a genuine and unfiltered look at the relationship between Ferrell and Steele as they navigate the complexities of transition, identity, and societal change. The film is also a meditation on love—love in its most unconditional form. Ferrell’s support of his friend is unwavering, and he continually seeks to make her feel comfortable, safe, and seen in a world that often marginalizes trans people. As the journey unfolds, their shared moments of laughter and vulnerability offer a poignant reflection on the beauty of authentic human connection. The documentary’s humor, too, is an integral part of its narrative. While it was originally conceived as a comedy, the filmmakers wisely allowed the humor to emerge organically rather than trying to force comedic moments. This makes the film feel authentic, grounded, and deeply relatable. Ferrell’s natural comedic timing, paired with Harper’s sharp wit and insight, ensures that the film doesn’t shy away from humor—even in the most serious of moments. The interplay between humor and pathos gives the documentary a unique tone, blending entertainment with education and making it accessible to a broad audience. 
 
"Will & Harper" premiered at the 40th Sundance Film Festival in January 2024, where it was met with overwhelmingly positive reviews. Critics have praised the film for its honesty, emotional depth, and the dynamic between Ferrell and Steele. On the review aggregator website Rotten Tomatoes, the film received a 99% approval rating from 90 critics, with an average score of 7.9/10. The site’s consensus reads: "Endearing and heartfelt, "Will & Harper" is an ode and testament to long-lasting love, acceptance and evolution within a friendship." Metacritic similarly gave the film a score of 75/100, indicating generally favorable reviews. Manohla Dargis of "The New York Times" described the documentary as "a transcendent road trip," while Taylor Gates of "Collider" gave it an 8/10, calling it a "must-watch." The film also drew praise for its ability to balance educational elements with the natural humor of Ferrell and Steele's relationship. Critics noted that the documentary effectively humanizes the trans experience, offering both a deeply personal account and a broader societal commentary on the struggles faced by the trans community. The documentary also provides a much-needed perspective on the issues of misgendering, discrimination, and transphobia that many trans individuals face. By capturing these moments in a real and raw way, "Will & Harper" helps to humanize these struggles, showing that despite the adversity, there is strength in authenticity and friendship. 
 
In a time when the visibility of the LGBTQ+ community, particularly trans individuals, is under increasing scrutiny and challenge, "Will & Harper" stands as a beacon of compassion, friendship, and understanding. The documentary’s honest portrayal of Harper Steele’s journey, combined with the unconditional support of Will Ferrell, offers an inspiring example of how love and friendship can transcend societal barriers. By celebrating Harper’s journey of self-discovery and highlighting the power of supportive relationships, "Will & Harper" encourages viewers to reflect on their own relationships and the importance of standing up for those who are marginalized. Ultimately, "Will & Harper" is not just a documentary about a road trip across the United States. It is a celebration of friendship, a testament to the resilience of the human spirit, and a powerful reminder of the importance of love and acceptance in a world that often feels divided.
 
via: youtube
Image credits: YouTube

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