‘Will & Harper’ Review – A Powerful, Moving Journey Of Discovery Between Two Old Friends [TIFF 2024]

When Will Ferrell is in the room, you know. It’s easy to say that “there’s just this thing about him” because he’s so recognizable, but he also makes sure that you’re aware of his presence. Whether he’s wearing a Los Angeles Kings hockey sweatshirt or donning a fu manchu mustache and a wig that looks like he took a trip to Kris Jenner’s hairdresser, he’s boisterous, commanding, and ultra-famous. So it’s no surprise that, upon entering The Big Texan Steak Ranch in Amarillo, Texas while wearing a detective outfit and loudly proclaiming to be Sherlock Holmes, he was found out. Beyond the pipe, the robe, and his trademark deerstalker, there wasn’t much sleuthing for onlooking patrons to do.

What typically happens when someone like Will Ferrell enters a public establishment with all the stealth of an eighteen-wheeler in a bowling alley is that people are both surprised and thrilled to be in his midst. But the reception in Amarillo was of an icier variety. After ordering the restaurant’s daunting 72-ounce steak, Ferrell encouraged the waiter to introduce not just him, but his friend, Harper Steele, a former head writer on Saturday Night Live where she and Ferrell met and worked together for years. It shouldn’t have been a big deal, one friend acknowledging the other. But in Texas, Harper’s attendance was anything but welcome. “Will Ferrell and Harper… uh, Miss Harper Steele!” the waiter shouted, struggling to acknowledge the woman sitting in front of him with her proper pronouns. 

A transgender woman, this wasn’t the first time Harper had been misgendered – the waiter had previously called her “Sir” – but it was the first time it had ever happened in Texas, a state with heavy restrictions on medications and surgeries required in order to transition. The response the two old pals got was both vile and heartbreaking. It didn’t even help that both Will and Harper knew what they were walking into when they opted to stop at that restaurant in that state. 

This pit stop, one of many taken in a cross-country road trip, comes roughly three-quarters of the way into Josh Greenbaum’s documentary, Will & Harper, though it feels important to note it upfront. For while much of Ferrell and Steele’s pilgrimage from Staatsburg, New York to Mojave, California – a conceit contrived by Ferrell in an effort to better understand the impact of Harper’s transition on their relationship, for better, worse, or neither – is exactly what you’d expect from a voyage being shared by two successful comedians, not one minute of this strong, sincere documentary shies away from the fact that the experience of a transgender person in America is a complicated, oft-dangerous one. Even if it isn’t always successful in how it conjures revelations on that subject, it broaches them; sometimes, that’s enough.

The journey began thusly: In 2021, Ferrell received an email from the person he had only ever known as Andrew Steele (Harper’s dead name, referenced very briefly) informing him that she intended to go through gender transition. It might have come as something of a shock to Ferrell and others who received Steele’s message — a list including Tina Fey, Seth Meyers, Kristen Wiig, and her two children — but for Steele, it was the natural next step in a life that, to that point, had been lived as a lie. Her truth is placed under a consenting microscope here, as she and Ferrell travel from state to state, conversing along the drive about how Ferrell received the news, how Steele went about delivering it, and much more beyond the specific parameters of her transition.

Much of what makes Will & Harper as powerful as it can possibly be is, of course, due to the second-nature quality that Ferrell and Steele’s relationship has, and the former’s willingness to learn as opposed to shying away from the “hard” questions in favor of an easier digestive period is as heartening as it is expected. What’s more, Ferrell further authenticates his own experience by making mistakes; when he and Harper attend an Indiana Pacers game, they encounter the state’s governor, who banned gender-affirming care for minors in 2023, unbeknownst to the duo. Between that, the aforementioned steak dinner, and even a Las Vegas-set dinner that sees Ferrell dressed in costume, much of the actor’s efforts to take the pressure off of Harper indirectly take away from her own comfort. To her credit, she addresses it; in all of these instances, Ferrell expresses remorse, to which Steele responds kindly, noting that at least he’s willing to learn.

That’s primarily where the film’s strength lies, in the fact that it exists at all. Plenty of celebrities shy away from the spotlight when it comes to speaking on gender affirmation, and that Ferrell immediately took an interest in his friend’s story has been recognized with praise in the days since the trailer’s release. There are versions of Will & Harper – literally, one of them was almost made – in which comedic moments are scripted rather than genuine. Instead, the camera’s presence is rarely felt, generally lingering on Ferrell and Steele in conversation, whether over the shoulder of someone drinking with the duo in a crowded Oklahoma bar, or planted on the front of the station wagon they haplessly elected to drive across the country. (Miraculously, it never broke down.) 

The times when the camera does feel apparent are the only time the film seems somewhat synthetic. There are more than a few occasions where Greenbaum, who last directed 2021’s Barb & Star Go to Vista del Mar, places an emphasis on Harper’s “features,” if you will. Her painted nails; her endless collection of heels. For all of Will & Harper’s talk about accepting one’s self for who they are — Harper is the same person, just more herself than she’s ever felt — paying so much attention to her appearance feels as though it’s intended to highlight how she’s different. It’s counterproductive and feels out of place in a film that otherwise hammers home a most important fact: Being trans doesn’t make you any less you. In fact, the inverse is true.

But Greenbaum knows this, and perhaps acknowledging them in the first place is one way of nit-picking a film that has no picks to nit due to how easy it is at its core. The road trip is merely a manufactured way for Ferrell and Steele to reconnect, and there’s nothing wrong with highlighting the trans experience in a documentary of this nature, a fact that remains true despite it not having too much to add in regards to what it means to be trans in America. That, I’d argue, is the opposite of Will & Harper’s point; rather, it is interested — and successful — in depicting the singular experience of one woman, as well as the singular response to her transition from her friend, a man. Its filmmaking shortcomings and conventions matter significantly less than the importance of the sum of its parts.

Will & Harper held its International Premiere as part of the Gala Presentations section at the 2024 Toronto International Film Festival. The film will be released in select theaters on September 13th courtesy of Netflix before debuting on the streaming platform on September 27, 2024. 

Director: Josh Greenbaum

Rated: R

Runtime: 114m