If the introduction of Josh Greenbaum’s Will & Harper (2024) makes one fact clear, it’s that Will Ferrell deeply admires his close friend Harper Steele.

Not just for their 27 years of friendship, beginning on Saturday Night Live in the late ‘90s, but the countless memories they’ve collected. Described as “a loveable curmudgeon with a great sense of humor” by Ferrell, the pair remain close friends to this day.

In 2022 at age 61, Steele reached out to Ferrell informing him of her intention to go through gender transition. In that moment, Ferrell realized he had a lot of questions not just about Harper’s transition, but about the trans community in general. Soon after, the pair decide to venture out on a 16-day cross-country road trip from Staatsburg, New York to Los Angeles, California, with Ferrell helping Steele gain more confidence as her newly established self.

On paper, the premise of Will & Harper is incredibly admirable and a beautiful gift to a friend, and, for that reason alone, it’s impossible not to see the innate value of perspective the film offers. However, the film is admittedly stronger in concept than in practice when translated into a fully fleshed-out documentary.

The exploration has emotional high points and poignant moments of clarity that ultimately make it worth recommending. However, to get to those moments, there’s a lot of meandering humor and less impactful detours to sit through.

The film starts strong with a frank admission of ignorance by Ferrell in the wake of Harper’s emergence as a transgender woman. The throughline that Will & Harper establishes early on is one of acceptance and understanding, and what better way to support a friend than by escorting her through rural America as she tries to find her true self?

It’s in the moments of Steele and Ferrell’s bonding and the latter’s questions for understanding that the film finds the harmony it sets out to discover. Steele addresses every conceivable question one may have, including, “Have you always felt like you’re a woman?” “What does it feel like to have your body not match how you feel internally?” “Why did you choose the name Harper?” And she does so with patience and grace.

Will & Harper, at its best, operates as an opportunity to explore the feelings of rural America, the public perception of the trans community, and the disconnect between online noise and actual experience. The stark difference between when the pair break bread with red-blooded, conservative Americans in a bar in Meeker, Oklahoma, and how they’re ruthlessly harassed online after appearing at an Amarillo, Texas steakhouse is a fascinating paradox.

The same can be said for a harrowing scene at the Grand Canyon where the pair meet a retired therapist who asks about Harper’s transition. The regret the therapist feels when she looks back on how she handled a client’s struggle with gender identity is palpable; A regrettable lapse in the struggle for progress in how the trans community is understood that can’t be mended.

When Will & Harper is pointed and focused on exploring this juxtaposition, the film is excellent. However, the problem with the film has more to do with the film’s lengthy runtime and recognizable filler in getting there.

It’s understandable that a film about a friendship involving an SNL cast member and writer would make sense to involve their fellow members, but the film either needed to use them sparingly or utilize them as interview subjects.

The running joke of wanting Kristen Wiig to write a “jazzy theme song” for the film after a FaceTime call, only to not connect with Wiig for the rest of the movie ultimately feels pointless. The same can be said for a scene where the pair meet up with Will Forte to go air ballooning in Albuquerque. It’s great to see Forte, but the scene adds little to the overall experience.

The same can be said for the humor that pieces the film together. Ferrell is an actor who’s capable of being very funny with the right writing and supporting cast behind him, but on his own, he’s never been a strong improvisationalist. Not to mention two separate running jokes involving Pringles and Dunkin’ Donuts that never feel like anything other than shallow product placements.

Take out these pointless asides, keep the focus on Harper’s journey, and the major problems are gone, yet these nagging issues stop Will & Harper from reaching greatness.

There’s a universe where Will & Harper could work better as a scripted comedy. The possibility of the pair bobbing and weaving across the country, recontextualizing their friendship as they learn more about each other and themselves, has a lot of promise.

As is though, Will & Harper makes for a serviceable, but charming documentary. As much as Ferrell’s celebrity status overshadows Harper’s prevalence on the road place to place, Ferrell always gives Harper the support and distance she requires to make her voice heard.

As a documentary, some aspects need tightening. As a gesture to a friend and gateway into trans acceptance on a worldwide scale, Will & Harper deserves the spotlight.

Review Courtesy of Landon Defever

Feature Image Credit to Netflix via Them