Movie Review ~ Will & Harper

As Saturday Night Live begins its landmark 50th season, there have been a few stories of the writers, producers, cast members, and guests that have made it into a television institution for the past half-century.  Jason Reitman’s so-so feature film about the first episode is now playing in theaters (gosh, I wish that film was better or, y’know, surprising in any way), and you can look on numerous streaming services to see the success of any number of SNL’s alum over the years. 

There’s one project, though, that stands out as distinctly unique. While it draws inspiration from SNL, that’s not its primary focus. Premiering at Sundance (after I had already flown home) and playing at the 2024 Toronto International Film Festival, Will & Harper, a documentary by Josh Greenbaum, offers a fascinating glimpse into the enduring friendship of Will Ferrell and Harper Steele. 

Ferrell and Steele have known one another since they both worked on SNL, joining the long-running sketch comedy show in 1995. As Ferrell’s star took off into the stratosphere, he left in 2002 to continue his movie career, occasionally returning as a guest host or in cameos. Steele remained until 2008 when they became the creative director of Funny or Die, the production company Ferrell founded with three others. 

Though the two remained close and kept in contact through email during the COVID pandemic, it wasn’t until 2022 that Steele, assigned male at birth, came out to her friends and family as transgender and began gender transition.  During the following days, weeks, and months, a similar transition of hearts and minds took place, with Steele’s freedom to embrace who she always was being met with acceptance from most and the need for processing time for some. 

In Greenbaum’s (Barb and Star Go to Vista Del Mar) documentary, we witness the profound evolution of the friendship between Ferrell and Steele as they embark on one of Steele’s favorite pastimes, the cross-country road trip.  Uncertain how safe it will be to travel to the usual places she used to stop on previous solo trips and how different parts of the country will react to a transgender woman in their small-town dive bar, Steele agrees to take the journey with Ferrell, discussing their lives along the way.  What begins as a simple trek from New York to Los Angeles becomes a deeply moving reflection on friendship, identity, and acceptance, set against a changing America.

Shot over 16 days, the two revisit places significant to their careers and off-camera lives, stopping by to see friends (famous and non) along the way.  Greenbaum allows Will & Harper to be emotional and funny without being heavy-handed or coming off as phony.  Ferrell, known for his always-on wacky roles, comes off less as a performer and more as a sincerely supportive friend.  There’s a vulnerability they both share that strengthens their bond and allows us to see inside the mechanics of their long-lasting friendship.  Steele, lesser known to us on camera but whose influence on many of SNL’s unforgettable classic bits (The ‘Oops! I Crapped My Pants’ commercial) is astounding, is shown to be witty and warm as she courageously embraces her true self.

However, Will & Harper avoids truly venturing into the harsher realities many trans people face, often showing the Ferrell/Steele journey through a lens of obvious privilege.  Most people, even from the heartland of America, are smart enough not to be caught on camera showing their true ugly side, especially in this day and age of cancel culture and public shaming.  The safety net surrounding Ferrell and Steele doesn’t detract from the emotional center of the story or mission of the movie Greenbaum is making. Still, there is room for a more grounded representation. 

Ultimately, Will & Harper is a celebration of friendship and unconditional support. Greenbaum balances meaningful conversations and lighthearted moments (one of which backfires with extreme consequences for Ferrell) to keep the film in feel-good territory. Often touching and always thought-provoking, the film’s depiction of loyalty and showing up for the people who matter is powerful.