In a world where stories of gender identity are often oversimplified or overlooked, Harper Steele’s memoir promises to be an intimate and necessary exploration of one’s personal journey through transition. Best known as a head writer for Saturday Night Live (SNL) and a co-writer of films like Eurovision Song Contest: The Story of Fire Saga, Steele’s transition at the age of 61 has brought new light to both her creative work and her personal life. But it’s not just the memoir that has made headlines; it’s her friendship with comedian Will Ferrell and the way their dynamic has shifted in the wake of her gender transition.
Steele, whose career has been steeped in writing and comedy, is embarking on a journey to share her story in a memoir that reflects on her experience as a transgender woman. Speaking with Gayety at the GLAAD Media Wards, Steele revealed that writing her memoir has been a deeply personal process. “I’ve kind of always wanted to tell my trans story because I didn’t see it in a lot of other people’s stories,” Steele shared. For Steele, telling her truth is not only an act of self-expression but an act of representation. As someone who has navigated the complexities of gender identity, she hopes her memoir will give voice to others who may be struggling with similar experiences.
View this post on Instagram
However, the path to writing her memoir hasn’t been an easy one. Steele candidly explained that uncovering the truth about her life has at times been difficult. “Uncovering the truth is sometimes very difficult, and it takes a little while to get there,” she said. As any writer can attest, delving into the past, especially when it involves deeply personal topics such as gender identity, can be a painful and exhausting process. But for Steele, it is necessary. Her memoir is not just about her transition but about understanding the long road to acceptance and the challenges that have shaped her.
Steele’s decision to write a memoir is not just a professional undertaking but a means of claiming her space in a world that often marginalizes trans voices. Her journey, marked by courage and a deep desire to share her experience, is one of resilience. Through her memoir, she hopes to fill a gap in the literary world by offering a nuanced portrayal of what it means to be transgender. It’s a story that goes beyond the typical narratives we often see in the media, exploring not just the transition but the mental health struggles, social challenges, and moments of triumph along the way.
At the heart of Steele’s memoir is her friendship with Will Ferrell, who has been by her side for nearly three decades. The two first met when Ferrell joined Saturday Night Live in 1995. Over the years, their friendship deepened, leading to shared projects like The Ladies Man and Eurovision Song Contest: The Story of Fire Saga, both of which Steele helped co-write. The dynamic between the two is incredibly close, and Ferrell has been one of the few people who has witnessed Steele’s journey from a distance, offering support without judgment.
Harper Steele accepts the Outstanding Documentary award for “Will & Harper” onstage during the 36th Annual GLAAD Media Awards at The Beverly Hilton on March 27, 2025 in Beverly Hills, California. (Photo by Matt Winkelmeyer/Getty Images for GLAAD)
In the Netflix documentary Will and Harper, directed by Josh Greenbaum, Ferrell and Steele embark on a 17-day road trip from New York to Los Angeles. During this journey, they have raw, honest conversations about Steele’s transition and the emotions that come with it. The film, much like the memoir, is marked by the vulnerability of both participants. Ferrell and Steele, though often fumbling in their conversations, make a conscious effort to listen and understand one another. The trip highlights not just their individual experiences but the shifts in their friendship as they navigate this new chapter together.
Throughout their journey, Ferrell displays a newfound sense of protectiveness toward Steele, something that was absent during their previous years of friendship. This emotional evolution is subtle but profound, especially considering their past as comedic collaborators. Ferrell himself admits that he doesn’t have all the answers on how to navigate this shift, but his compassion for Steele’s experience is evident in every conversation. The film also touches on moments of humor, such as when Ferrell jokingly asks Steele if she’s a worse driver now that she’s a woman. While lighthearted, these moments serve as an important reminder that humor can help bridge the gap in difficult discussions, even when the subject matter is deeply personal.
However, the documentary also delves into the more challenging realities of being transgender, particularly in a world that is increasingly hostile toward the LGBTQ+ community. A particularly poignant moment occurs when the pair stops at an Indiana Pacers game and takes a photo with Governor Eric Holcomb, who recently signed a controversial bill banning gender-affirming care for minors. This encounter prompts a serious discussion between Ferrell and Steele about the political and cultural implications of such laws. For Steele, the fear of not being safe in certain places is compounded by the fact that she is not just a woman but a transgender woman.
Steele’s memoir, much like the documentary, explores the intersection of personal identity and societal challenges. Her experience of moving through the world as a trans woman in a society that often marginalizes or outright rejects gender diversity is not just a personal narrative but a reflection of the broader cultural struggles that continue to affect many in the transgender community.
As she continues to work on her memoir, Steele remains committed to telling her story with honesty and vulnerability. It is her hope that her words will help others who may be navigating similar paths feel less isolated and more understood. In a world where transgender voices are often overlooked or misunderstood, Steele’s memoir promises to be a beacon of hope, offering both representation and recognition of the struggles that come with being true to oneself.
Steele’s journey is far from over, but as she writes her memoir and reflects on her transition, she is paving the way for more stories like hers to be told. Her friendship with Ferrell, marked by mutual respect, humor, and compassion, is a testament to the power of unconditional support and understanding, even when faced with the complexities of gender and identity. For Steele, writing her memoir is not just about recounting her past but ensuring that future generations of transgender individuals have the representation they deserve.
