Will & Harper is a charming, honest look at transitioning and allyship

During Will Ferrell’s tenure at Saturday Night Live, he met a writer named Andrew Steele, who he hit it off with immediately. The pair proved an effective combination, both on the show and after Ferrell’s departure (Steele remained on SNL’s writing staff and was one of the head writers between 2004-2008). Steele was the writer behind the Ferrell vehicles Casa de mi Padre, The Spoils Before Dying, The Spoils of Babylon, A Deadly Adoption and (perhaps most delightfully) Eurovision Song Contest: The Story of Fire Saga. 

In 2021, Ferrell received an email from Steele to let him know she was transitioning to live as a woman, and was now Harper Steele. While the news took Ferrell by surprise, he was immediately supportive. There were, of course, a lot of changes to navigate; before transitioning, Harper loved road tripping to remote places and talking to strangers in small-town dive bars. How much of that could she still do safely as a transwoman? Would her closest friends still be there for her, or would some of those relationships no longer be the same?

Steele’s questions and doubts, and Ferrell’s desire to get to know his long-time friend’s authentic self (and accompanying nervousness about saying the wrong thing) are highly relatable. Luckily for all of us, the pair chose to document their journey together with Will & Harper. The film, directed by Josh Greenbaum, follows the friends on a cross-country road trip with Ferrell serving as a safe person to help Harper re-engage with the world. 

As an authentic journey of a trans person engaging with the world, Will & Harper doesn’t always work (most trans women don’t have a celebrity best pal to stand by their side). As a depiction of allyship, however, it’s an affirming illustration of someone trying their best to do right by their friend and learning in the moment what that requires, as their friend simultaneously tries to figure out what they need and how to ask for it.

Ferrell and Steele’s trip has plenty of feel-good encounters with folks you wouldn’t expect to be accepting of Steele’s transition, but it also doesn’t veer away from the real dangers trans people face in America. There are moments the pair confront anti-trans government policies, or find themselves in unwelcoming or dangerous situations. On the whole, the journey requires a lot of vulnerability from both Steele and Ferrell, on top of Steele’s existing vulnerability over coming out in the first place. 

Ferrell’s recognizable celebrity status also proves to be a stumbling block to Steele interacting with strangers on her own terms. Their attempts to get around that lead to moments both tense (Steele insisting on visiting a pro-Trump biker bar in Oklahoma by herself before Ferrell comes in) and sweetly funny (Ferrell trying to give Steele a nice night out in Las Vegas by donning a costume so the evening doesn’t become about him).

On that note, it’s valuable that Ferrell isn’t a perfect ally, and he knows that going in. He’s well-meaning but occasionally awkward, curious, but worried his questions might come off as insensitive, eager to help but sometimes not recognizing his privilege until it’s almost too late (he’s always apologetic when it happens, and learns from the experience). In other words, he’s like most of us, which is a relief.

Will & Harper is both a gentle exploration of how to interact with a friend after they’ve transitioned, and the triumphs and pitfalls of navigating relationships and the world after transitioning. There’s no way to keep the story from being cushioned, but everyone involved deserves respect for being upfront and honest about their feelings—prickly as they sometimes are—at every stage. This movie is going to help a lot of people start important conversations they may have been afraid to have, and it’s hard to think of a nobler achievement than that.