Drew Burnett Gregory is back at TIFF, reporting daily with queer movie reviews from one of the world’s most prestigious film festivals. Follow along for her coverage of the best in LGBTQ+ cinema and beyond.

It’s more challenging to transition than to know someone transitioning. But our world has not been conditioned to understand nor empathize with the trans experience. It’s easier for a cis person who doesn’t know any trans people — or doesn’t know any well — to empathize instead with the person’s family or friends or even strangers they interact with. When a cis person is close friends with a trans person, they still might better understand an experience more like their own. For example, after Harper Steele is misgendered at a diner, her long-time friend Will Ferrell says, “Well, it’s going to happen.”

Most people will think the new documentary about their friendship, Will and Harper, is inspirational, a beautiful portrait of love and acceptance. But, in my opinion, the most interesting aspects of the movie are the ways Will falls short. This is not a critique of him. Rather, I think it’s important to show the value in love without perfection. It’s more challenging to transition than to know someone transitioning — that doesn’t mean there aren’t still challenges and questions for the loved one. Mistakes will happen and if these mistakes can be acknowledged, less idealized more genuine relationships can form. Will and Harper isn’t a portrait of transness in America as much as it’s a portrait of friendship, a portrait of trying.

Harper Steele and Will Ferrell met on Saturday Night Live where Harper would go on to be the head writer. They’ve worked together on several projects post-SNL including The Spoils of Babylon and Eurovision Song Contest: The Story of Fire Saga. Then Harper came out as trans to Will and everyone else in her life in 2021 at the age of 61. The film follows a 17 day road trip between the two friends — a trip suggested by Will and motivated by Harper’s desire to visit the spaces across the country she’s frequented her whole life. What does it mean to go to a basketball game or walk into a dive bar as an out trans woman? Will Harper still be welcomed?

The wisest decision of the film is that it doesn’t pretend to be universal. There’s a difference between going to these spaces as a trans woman and going to these spaces as a trans woman relatively newly out alongside the very famous Will Ferrell. It’s within this specificity that the film finds its most interesting threads. Harper and Will both have eyes on them at all times for very different reasons. Will’s reaction to fame is to lean in, to be loud, to do bits, and that approach, at times, makes the trip more challenging for Harper. Other times, Will’s celebrity makes people more inclined to see Harper as worthy of respect and humanity. It’s a complicated balance and throughout the road trip Will has to learn the ways he has to now alter his behavior with his friend — not because of her differences but because of how the world now treats her.

There’s a real joy to spending time with Harper and Will and their relationship. Not only are they funny, but here they’re funny in a way only possible with intimacy. The documentary feels like sitting in on the very best of inside jokes. Some of the film’s greatest moments aren’t at any of their various stops, but when the two of them are just on the road.

Because the dynamic is so strong, I wish the film trusted its audience more. I understand this is a documentary made primarily for people with minimal knowledge of transness, but I wonder if there’s a value to inviting people to catch up rather than talking down to them. This is especially true in the beginning. There is a difference between Harper later referring to her deadname and speaking in complicated terms about the persona she built throughout her life and the film itself introducing Harper in the way cis people have been sensationalizing us for decades.

When Elliot Page came out, GLAAD — who consulted on this documentary — released a style guide that gave publications permission to deadname Page for clarity. I’m not offended by this suggestion, but I do question its necessity. That feels even more obvious here when Harper was not a household name. The framing of Will talking about his friend with her old name and he/him pronouns and then revealing Harper’s transition as a sort of early twist feels so much less sophisticated than the rest of the film.

Trans people have never been new, but the overwhelming amount of visibility we’ve experienced over the last decade means we need to start shifting how we’re talked about. What may have once seemed like an obvious narrative framing, might now be unnecessary. I want to push forward. I want cis people to be challenged rather than appeased.

And yet, just like Will doesn’t have to be perfect to be a great friend to Harper, this documentary doesn’t need to be perfect to be meaningful. There are many gems within this footage and, for the most part, director Josh Greenbaum lets the well-curated footage tell the story and tell it well.

At one point, Harper is lamenting how long it took for her to come out. She then acknowledges that had she come out she certainly would not have, say, been the head writer at SNL. No matter when a trans person comes out, there’s a lot of value in recognizing the ways our lives are more than just the challenges of being trans in this world — before we came out and after. But imagine a world where Harper could have come out as a teen and still been the head writer at SNL. Imagine a world where we didn’t have to suffer for so many years before people either reject us or call us brave. Imagine if we could just be comedy writers and friends and women and/or whatever else we wanted to be beyond our transness.

I’m excited for people like my family to watch this documentary. I’m even more excited to see what scripts Harper writes now that she’s not hiding this part of herself. She’s great as a documentary subject — she’s even better as an artist of her own.

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