The Saturday Night Live alums and longtime writing partners make for a funny pair as friends discovering more about each other during a 17-day drive across the United States…
In the first few minutes of Will & Harper, the new documentary that had its international premiere at the Toronto International Film Festival this week, actor Will Ferrell explains his longtime relationship with comedy writer Harper Steele. A partnership that the actor claims is primarily responsible for any movie that Ferrell has been a part of in which his fans could ask, “Why would Will Ferrell do this movie?”
These projects include Eurovision Song Contest: The Story of Fire Saga, A Deadly Adoption, and the Spanish-language movie Casa de mi Padre, among others. But the two met when they were both involved with Saturday Night Live, a series that saw Steele rise the ranks to become Head Writer. What makes this friendship and professional relationship fascinating is that Steele identified as a man during most of these years…until now.
Harper Steele once went by a different name, but now that she’s transitioned, she’s chosen the name Harper to honor the writer Harper Lee of To Kill a Mockingbird fame. This revelation comes out during the first moments of a 17-day road trip between Ferrell and Steele, of which they embark from New York City to the West Coast of California. Driving most of the old Route 66, the two compadres discuss their years of friendship and what the trans experience is like for Harper since coming out to all of her friends, family, and essentially the world.
The road trip is meant to be a bonding experience, but several other facets bring Will & Harper to an immediately captivating place. Steele used to travel the United States for decades alone, stopping in dive bars and sleeping in dilapidated motels, which Steele took great pleasure in. It’s in these remote small towns that Steele felt alive, talking to random strangers and discovering something new about the United States every mile driven from coast to coast.
But the idea of traversing across the country with her buddy Will is a sobering thought for Steele, as this will be the first chance she’s had to debut her new look to what she perceives as unfriendly conservative territory towards trans people. Their journey has massive surprises, as the small-town folks they encounter often defy expectations and welcome her with open arms. Well, most towns do, with the exception of a failed dinner in a famous steakhouse in Amarillo, Texas, that goes haywire fast for the famous actor and his longtime pal.
At the heart of Will & Harper is a friendship rendered anew as Steele gets to live her truth along with a close friend for the first time in her life. But Will has some questions for her, just like any of us would have if we found out our friend was shielding part of their identity for as long as we’ve known them. Through long-distance driving, endless conversations, accepting mistakes and misunderstandings, meeting up with old SNL friends, and seeing the sights of an expansive country, Will and Harper learn more about one another in 17 days than they have in 30 years.
The documentary is bookended by a promise of an original song by actress Kristen Wiig, another friend of Steele’s who has completely accepted her transition. When it eventually plays during the film’s end credits, it is absolutely worth the listen. It is marked by Wiig’s comedy chops and subtle references to Steele’s trans experience. It’s heartfelt, moving, and funny, and it might just be in the conversation for Best Original Song during awards season.
Will & Harper is a sincere look at trans issues in deep red America, as seen through the eyes of a well-established writer who reasonably knows what it feels like to put on a dress and makeup while getting stared at by onlookers. It doesn’t help that her partner in driving crime is a world-famous actor, as many of their adventures go viral on social media almost immediately. However, through this relationship and what they observe within one another, the documentary hits its high marks, something director Josh Greenbaum knows how to navigate wonderfully in this earnest attempt.
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