Josh Greenbaum’s documentary Will & Harper is far more than a simple road movie; it’s a deeply introspective exploration of identity, belonging, and the courage to live authentically. Following Harper Steele, a trans woman who once presented as a man named Andrew, and her close friend, comedian Will Ferrell, the documentary captures their journey across the country as they reflect on who they are and how the world perceives them. Set against the backdrop of small-town America, their road trip from New York City to Los Angeles takes on a symbolic weight as Harper revisits the places where she once felt at home, now questioning if those spaces can still accept her true self.
The documentary isn’t just a physical journey but also a profound emotional test, raising key questions about identity and society’s capacity for inclusion. Along the way, Will & Harper delivers powerful lessons about authenticity, friendship, fear, and resilience. Below, we delve into the key teachings that emerge from their remarkable journey.
1. Embracing Authenticity
Harper’s transition from living as Andrew to embracing her identity as a trans woman serves as a central theme of the film. Her willingness to confront her fears and live her truth, despite the challenges she faces, is a lesson in courage and self-acceptance. The documentary reminds us that living authentically is essential, even if it requires confronting societal judgments and inner doubts. Harper’s story teaches us that we are at peace with ourselves only when we embrace who we truly are.
2. Facing Fear and Uncertainty
As Harper returns to places that once felt like home—dive bars, diners, and motels—she is forced to grapple with new fears. Before transitioning, she felt free to navigate these spaces without concern. Now, as a trans woman, she faces the harsh reality that these same places may no longer offer her safety. This transformation highlights a profound lesson: fear is often a necessary companion on the journey to self-discovery, but it can also serve as a teacher, guiding us toward greater understanding and resilience.
3. Questioning Societal Norms
Harper’s road trip through stereotypically American settings raises larger questions about whether these traditional spaces—rural Oklahoma dive bars, Texas steakhouses—can still accommodate diversity, particularly for trans individuals. In doing so, the documentary challenges viewers to question whether societal institutions are as inclusive as they claim to be. Harper’s journey suggests that while progress has been made, many spaces still have a long way to go in creating environments that are welcoming to everyone, regardless of identity.
4. The Power of Friendship
Will Ferrell’s role in Harper’s journey is one of unconditional support. As a famous figure, Ferrell is no stranger to public attention, but he comes to realize that the scrutiny he faces is vastly different from the type of attention Harper endures as a visibly trans woman. His presence provides comfort, but he also gives Harper the space to navigate her own journey. This dynamic teaches us about the importance of friendship—being there for those we love while respecting their need for independence and self-growth.
5. Resilience in the Face of Scrutiny
Harper’s journey into these traditionally conservative spaces highlights her resilience. Despite the uncertainty of how she will be received, she confronts her fears and revisits the places that once brought her joy. This resilience teaches us the power of perseverance in the face of adversity. Whether she’s entering a roadside bar alone or walking through unfamiliar towns, Harper shows that living authentically requires bravery in the face of potential hostility.
6. Redefining Belonging
One of the most poignant lessons in Will & Harper is Harper’s evolving relationship with the idea of belonging. The documentary raises the question: Do we belong to places, or do places belong to us? Harper’s journey suggests that belonging isn’t necessarily tied to geography but rather to personal growth. As she revisits the places that shaped her former self, she must reconcile her past with her present and redefine what it means to belong in a world where her identity has changed.
7. Navigating Privilege and Oppression
Ferrell’s experience as a cisgender man and a celebrity contrasts starkly with Harper’s experience as a trans woman. While Ferrell is used to being recognized wherever he goes, he learns that the attention he receives is largely positive—something that Harper cannot always count on. This contrast highlights the importance of acknowledging privilege and understanding the experiences of those who face oppression and scrutiny on a daily basis. Ferrell’s realization serves as a reminder that even well-meaning allies must continuously learn from those whose experiences are different from their own.
8. Courage to Explore Identity in Challenging Spaces
Harper’s willingness to step back into spaces that might no longer feel safe speaks to the courage required to explore identity in a world that can be hostile to difference. The documentary teaches that personal growth often involves revisiting familiar places with new eyes. This exploration of identity in challenging environments is a reminder that the journey toward self-acceptance is ongoing, and it often requires confronting the uncomfortable and unfamiliar.
9. Patience and Acceptance in Self-Discovery
Harper’s journey is gradual, reflecting the patient and deliberate nature of self-discovery. The documentary teaches us that growth is not always linear, and that it requires time, reflection, and a willingness to return to places we may have outgrown in order to fully understand who we are. Harper’s patience with herself, and her willingness to embrace her journey one step at a time, is a lesson for anyone struggling to find their place in the world.
10. The Importance of Representation
Perhaps one of the most vital lessons of Will & Harper is the need for representation. Harper’s story is not just her own; it reflects the broader experiences of many trans people who navigate spaces where they may not feel seen or accepted. The documentary underscores the importance of visibility and inclusion, showing that trans people belong in every corner of society, from dive bars to boardrooms. Harper’s courage to be visible, even in spaces that may not feel welcoming, serves as a powerful reminder that representation matters.
Conclusion
Will & Harper is a testament to the transformative power of authenticity, resilience, and friendship. Through their journey, Will and Harper offer us a window into the challenges and triumphs of self-discovery, while also prompting us to question our own beliefs about identity, belonging, and acceptance. Their story is a reminder that the road to living authentically is often fraught with fear and uncertainty, but it is also rich with growth, courage, and the possibility of redefining our place in the world.
As Harper navigates small-town America, she teaches us that belonging is not about where we are, but who we are. Her journey, accompanied by Ferrell’s unwavering support, shows us the profound impact of being true to ourselves—and the power of having someone by your side who believes in you along the way. Together, Will and Harper prove that the journey to self-acceptance is one of the most courageous and rewarding paths we can take.