Will & Harper Review: Two Friends, One Revelation-Filled Road Trip

Will Ferrell and former Saturday Night Live writer Harper Steele have been fast friends and creative partners for over 25 years. But when Steele made the courageous decision to transition to living as a woman at age 61, both she and Ferrell had questions about what it would mean for their enduring bond. Out of this was born the idea for Will & Harper, an openhearted documentary chronicling a cross-country road trip the longtime pals take to reconnect and gain insight into Steele’s journey as a trans woman traversing the backroads of America.

Directed with humor and heart by Josh Greenbaum, the film follows Ferrell and Steele’s amusing banter and profound conversations as they travel from New York to LA. With stops to reunite with SNL alums and make new friends in dive bars along the way, it captures both the comforting familiarity and eye-opening revelations that emerge when two people who’ve known each other for decades explore uncharted territory together. Part buddy comedy, part chronicle of self-discovery, Will & Harper promises a rare blend of belly laughs and teary-eyed moments. Audiences will likely walk away entertained, enlightened and deeply moved.

Two Comedic Minds, One Unbreakable Bond

Will Ferrell and Harper Steele first crossed paths on the set of Saturday Night Live in 1995. Though Ferrell was hired as a cast member and Steele as a writer, the two quickly discovered they were kindred spirits when it came to humor. Steele saw talent in Ferrell that others initially overlooked, writing many of the skits that would ultimately showcase his absurdist genius and cement his status as an SNL legend. Their comedic chemistry led to an instant connection that sparked a creative partnership and deep friendship spanning over 25 years.

Steele went on to collaborate with Ferrell as a writer on some of his most hilariously offbeat film projects – like the Spanish-language comedy Casa De Mi Padre, his surreal Lifetime movie A Deadly Adoption, and the gloriously weird Eurovision Song Contest: The Story of Fire Saga. Whenever Ferrell wanted to take an unconventional swing, Steele was in his corner spurring him on.

So when Steele made the profound decision to come out as transgender and begin transitioning to live as a woman at age 61, Ferrell was someone she knew would stand by her side. She broke the news to him frankly but tenderly via email, expressing her complex mix of fear and joy, while hoping their enduring bond would withstand this deeply personal transformation.

True to form, Ferrell offered his full support. But never one to do things by the book, he also proposed an appropriately eccentric gesture of solidarity – embarking on a cross-country road trip together so he could better understand his friend’s journey firsthand. Their willingess to steer into the skid exemplifies a relationship where encouragement, empathy and laughter conquer all.

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Back On The Open Road, But Is It Still Home?

When Harper Steele was presenting as male, she loved hopping in her vintage Grand Wagoneer and hitting the highways and dive bars of America’s heartland. But Steele worried her favorite pastimes might now seem off limits, or even dangerous, as an out trans woman.

So Will Ferrell hatched a plan – the duo would retrace the route of Steele’s glory days on a cross-country road trip from New York City to LA. With stops to reconnect with old SNL pals along the way, this would be her chance to revisit beloved haunts and find out if she still belonged.

As they cruise through middle America in Steele’s wood-paneled ride, she and Ferrell hold free-flowing talks covering everything – her transition, dating, passing, fashion, surgery, even suicide attempts. Their conversations capture what it really means to be an actively listening ally. Ferrell asks thoughtful questions out of care and curiosity, while Steele opens up with bracing honesty about her struggles to feel at home in her own skin.

Their exchanges tackle the harsh realities many trans people face, from hostility to violence. But they also reveal uplifting everyday acceptance. At a dive bar festooned with Confederate flags, Steele receives a raucous welcome. A girls’ night out in Vegas with showgirl headdresses brings pure joy. Still, a rude awakening comes during a steak dinner in Texas when transphobic abuse instantly floods the internet.

While Ferrell’s star power grants them privilege—and safety—in many spots, he also serves as an invaluable shield offering visibility and validation when tensions run hot. Questions emerge around intersecting marginalized identities lacking such security. But the answers lie in the allies who speak up.

Through open ears, minds and hearts, Will & Harper suggests a path where seeds of understanding can take root and grow. Its spirit echoes the age-old adage – it’s often the journey, not the destination, that changes us most.

Walking A Tonally Tricky Tightrope

In chronicling this deeply personal journey between two friends, director Josh Greenbaum faced a delicate balancing act. Will & Harper needed to capture the duo’s signature humor while also making space for emotional honesty around a sensitive subject. The final product manages to strike this balance more often than not, though the seams occasionally show.

The film wells up abundant laughter by simply letting Ferrell and Steele’s time-tested comedic chemistry speak for itself. Their familiar back-and-forth breeziness allows more profound matters to emerge organically. Yet Greenbaum also can’t resist constructing more manufactured reality-TV-style setups, like Ferrell dragging Steele to eat nothing but Dunkin’ Donuts.

Similarly, some conversations unfold with unfiltered candor, as when a tearful Ferrell apologizes for recklessly courting attention during a harassment-filled steakhouse dinner. But other poignant moments feel overtly stage-managed, aided by pop songs as subtle as a sledgehammer.

While Will & Harper largely succeeds as a warmhearted glimpse into a trans experience, its lapses into contrivance can briefly puncture the human connection. Still, much credit is due for meeting sincerity with sensitivity more often than not when humor mingles with hardship. In mirroring the highs and lows of life itself, the film finds its truest notes.

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Bridging Divides With Honesty and Humanity

While on the surface a feel-good buddy comedy, Will & Harper harbors deeper aspirations as a stealth tool for public education. By broadcasting an unfiltered glimpse into Harper Steele’s life as a transgender woman, the film spurs frank discussion of what that actually entails while putting a human face to an often demonized community.

As Steele fields Ferrell’s frequently awkward but well-intentioned questions, trans viewers may find catharsis and guidance about opening up to curious allies in their own lives. Cisgender audiences unfamiliar with trans experiences gain insight into the struggle for self-acceptance, the quest to simply feel safe, and the right way to extend support by listening rather than judging.

In traveling through the heart of a divided America, Will & Harper reveals reasons for optimism even in darkness. The friends discover hate hides everywhere, yet everyday people also open their doors wider than expected. While the film has blind spots around intersectionality, it makes strides capturing how trans women of color likely couldn’t make this trip alive.

Mostly, Will & Harper celebrates the incredible power of relationships. As Ferrell and Steele modeled, bonds fortified by trust can weather any storm. When humor and humanity converge, they hold the potential to radically reshape perspectives and save lives. With laughter and tears, this inspirational odd couple lights the way forward.

A Journey That Resonates Far and Wide

More than a moving chronicle of friendship or a star-studded lark, Will & Harper makes a stealth bid to widen perspectives on the road ahead for trans rights in America. While not without flaws in navigating such weighty themes, its big-hearted spirit remains unwavering.

In capturing both struggle and support on a quest to simply feel at home, the film presents a resonant window into the transgender experience. Moments of genuine connection and revelation, even amid discomfort, model how to bridge divides through open ears and minds.

Backed by Ferrell’s commercial appeal, Will & Harper should draw diverse crowds beyond the typical art house lane. Its crowdpleasing premiere points to likely distribution deals and even potential awards season play if acquired by a major buyer.

But more importantly, by putting humanity first, this poignant odd couple’s journey could help steer broader audiences towards empathy. In a nation still bitterly split, a story that makes space for outcasts and outliers deserves all the mileage it can get. Wherever it travels next, we could all stand to walk a few miles in their shoes.