Will and Harper (2024)

The premise of 2024’s Will and Harper is simple. During the covid-19 lockdown, comedian Will Farrell received an email from longtime friend and former SNL head writer Andy Steele that he was transitioning into a woman. Shortly after the email was sent, Andy became Harper. Harper is a lifelong fan of cross country road trips, and at that point the documentary practically wrote itself: Will and Harper would drive across the country together, navigating America’s twisty roads as they themselves navigated their friendship.

The trailer, like I said, is simple. The issues the film deals with are a bit more complex.

Throughout the film the pair make multiple stops as they work their way across the country from east to west. Outside the comfort zones of places like the SNL offices or Harper’s sister’s home, the pair are not always welcomed with open arms. Harper’s affinity for “real America” leads the pair to dive bars adorned with anti-Biden banners and Confederate flags, stock car races, and courtside at an NBA game — all locations intended to stoke a reaction because, let’s face it, conflict makes for good viewing. On multiple occasions conflict is diffused when people recognize Will Farrell.

The film’s most awkward moment comes when the pair spot The Big Texan in Amarillo, Texas — home of the infamous 72oz steak challenge. Farrell not only accepts the challenge (in which customers must eat a 72oz steak in under an hour along with sides like a baked potato and side salad), but does so while dressed as Sherlock Holmes. Somehow the two end up on a stage with spotlights pointed at them and even Farrell admits it’s one of the more awkward moments of his life. Ferrell’s attempt at comedy backfires as Harper must sit awkwardly with an entire restaurant staring at her. The Tweets that follow are shared on screen and are as bad if not worse than you can imagine.

Not every stop is as disastrous. Both of the pair’s stops in Oklahoma (one at a dive bar, the other at a dirt track racing event) are largely uneventful. Harper acknowledges that Farrell is her safety net, and that going into these places alone might not go as smoothly if she were navigating them alone. Even so, the pair never seem to face any direct conflict; at most they get the occasional awkward glance. Even Indiana governor Eric Holcomb (who signed a bill banning all gender-affirming health care in the state) smiles as he meets the pair courtside at a Pacers game.

As much as it is about the people they meet and the places they go, the film always returns to the pair’s relationship. Farrell asks the questions many of us are curious about, and Harper shares the pain and suffering she has endured along her journey. One of Harper’s goal is to “pass” (be identified as female), but her masculine face and build make that difficult. She is routinely misgendered by strangers and Ferrell does his best to introduce her as “Miss” Harper Steele, but when he shows up wearing a costume as the two dine in Las Vegas, it just makes it seem like she’s in one, too.

I went into Will and Harper assuming that the goal of this film was to change the way people think about transgender people. After watching the film, I don’t think that’s the case; at least, not in the way I originally thought. Harper doesn’t wanted to be treated like

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