Will & Harper Review: Funny, Heartbreaking, Beautiful, and Terrifying, All at Once

Being queer in 2024 sucks. Being queer in America in 2024 sucks even more. With the rise in hatred towards LGBT+ people – especially trans people in recent years – it doesn’t seem like things are getting any easier anytime soon. In the US in particular, there are swathes of townships and even entire states where simply being trans is not only unsafe, but borderline illegal.

Will & Harper aims to explore this animosity through the lens of Harper Steele, an openly trans woman who used to be the head writer of Saturday Night Live. Her best friend, Will Ferrell, joins her, as they travel across the US, including some of the more frustrating and terrifying parts.

The documentary opens with the two recalling a letter Steele sent to Ferrell, in which the former told the latter that she was trans. It’s a beautiful, touching letter for anyone with similar experiences, and knowing that Ferrell responded so kindly is genuinely lovely to know. Everybody deserves a person who accepts and loves them, and Ferrell loves and accepts Steele unconditionally.

Steele is the kind of person who loves to wander. Before her transition, she would drive endless distances across the US, stopping at shady bars in Trump-soaked counties, basketball games, and NASCAR races. After transitioning, she doesn’t really know if that’s something she can do anymore. And fair enough — these places can be unsafe for women in the first place, let alone trans women.

So Ferrell comes up with an idea. The two of them go together, to all these shady bars and aggressively cishet scattered throughout the country, with Ferrell being a buffer of sorts. Some folks might hate trans people, but when there’s a comedy superstar in the room, are they really going to act up?

For the most part, Will & Harper shows that, despite a few dicey moments, a trans woman can somewhat get by in a lot of the US. It won’t necessarily be the best experience, and things might be a little bit different than what they are for a cis man, but when you come face-to-face with the people who spout hatred online, most bite their tongues… at least with Will Ferrell by your side.

Both Steele and Ferrell recognise that they’re on the easy path here, and that things might not be so kind if Steele were on her own. I was worried going into it that this wouldn’t be mentioned, but it’s grappled with and explored, with neither under the illusion that this experience would work for the vast majority of trans people. It wouldn’t, and Steele knows that she’s incredibly lucky to be able to explore these experiences with a bit of a lifeline on her side.

Unfortunately, it’s not always a good time. While there are some genuinely touching moments where things go surprisingly well, there are some downright terrifying and heartbreaking moments, too. About midway through the documentary, Steele and Ferrell go to a Texas steakhouse and compete in an eating challenge with an absurdly large steak. Ferrell, hoping to take the attention away from his friend and put her mind at ease, does so dressed as Sherlock Holmes, and it backfires tremendously.

The following day, Ferrell reflects on the night before, in which being put in a literal spotlight caused a lot of hatred to be sent towards Steele. Not a lot of it was in-person, but the energy of the room was not positive, and the online haters didn’t hold back. It’s heartbreaking to see Ferrell break down upon the realization that his actions put Steele in a dangerous position. By shining the spotlight on the two of them in an unfamiliar, unsafe environment, he put Steele on the firing line.

It’s something that Ferrell hasn’t had to consider before — he gets hate all the time online, but he doesn’t let it get to him. It’s not so easy when you’re trans, where the hateful comments bounce around in your head, reflecting all the doubts and self-hatred you hold deep inside.

There are many powerful moments in Harper & Will, moments of both despair and of joy. Seeing the struggles that Steele has had to endure, many of which bubble up to the surface throughout their road trip, is a hard watch. But there’s genuine hope, too, that things might, someday, get better.

Small moments are scattered throughout that tug at the heartstrings. A trip to Goodwill so Steele can buy a dress for a nice night out might not seem like a big deal, but she did it alone, and she was treated by staff like any other woman would be. Those tiny moments of affirmation mean the world to LGBT+ people, and the quiet, contented joy on Steele’s face as she rifles through the racks of secondhand clothing is unforgettable.

There’s plenty of comedy, too, as you’d expect from a road trip featuring a comedy writer and a comedy actor. Steele and Ferrell bounce off each other with the energy that only two best friends could have, and it’s lovely to watch. A dumb joke about Pringles from Steele becomes an ongoing bit from Ferrell, and Ferrell’s pointed jokes about Steele’s womanhood feel loving in a way they might not had he been a stranger.

The openness with which they engage with each other is lovely to see, too. Steele encourages Ferrell to ask anything he wants, and the same is true in reverse. Ferrell wants to know what’s going on inside his friend’s head, how she feels, what she wants to do, and how she wants to do it, while Steele just wants to know that her friend still loves her, sees her as a woman, and is going to stick by her. Neither wants anything to change, but they both know that Steele simply existing as a trans woman makes life as a whole a much more difficult experience.

In a way, we get to see the two rediscover their friendship, penning a new chapter in their ongoing saga together without rewriting the past. The memories that the two shared are important to both of them, but the moments they’ll share going forward are even more important. This road trip is the first page in that new chapter, and it sets the terms of engagement going forward. As far as first pages go, I’d say it’s a pretty good one.

Will & Harper is a stunning documentary that just about everybody should watch. If you’re queer, it’s a must-watch, and if somebody in your life is trans, it’s even more crucial. It’s funny, heartbreaking, beautiful, and terrifying, all at once. Not many documentaries have that kind of range, but Will & Harper does.

Related: 7 Documentaries on Netflix You Must See