“Will & Harper” Review

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Everybody knows Will Ferrell, but few know Harper Steele. This is partly because she’s only been herself for a few years. For the past few decades, she was known as Andrew Steele, a Saturday Night Live writer from the 1990s. In 2022, she transitioned to a woman, and Ferrell wasn’t sure how to approach this development. That’s the basis for the documentary Will & Harper. It is as much about Will Ferrell learning to be a transgender ally as it is about Harper becoming more comfortable and open.

The essential conversations happen amid a cross-country road trip, where Will and Harper visit some familiar and new places. There are some reunions along the way, as when the two of them stop by their old stomping grounds of Saturday Night Live. There are some new connections made in small towns, harkening to Harper’s time growing up in Iowa. Of course, there’s that apprehension about venturing into small conservative towns, where taverns are lined with Trump campaign signs. Several stops are like testing grounds, as when Harper attempts to get accustomed to a small-town bar, only calling in Will when it’s all good and thankfully not when she needs social backup among bigots.

This is a new experience for both friends and the two of them approach the subject with cautious optimism. There tends to be this fear of not knowing how to interact with a transgender individual, as though one misuse of the pronouns will trigger a fury. But, as the film innocently showcases, Harper calmly corrects those who misgender her, sometimes playfully remarking, “Wanna try that again?” Will also probes with curiosity, slowly easing into asking his friend the bolder questions of surgeries and mental health. That said, he still finds the perfect moments for a joke, as when asking her if she brought her new rack to Nortstrom Rack, a witty question that Harper plays up as being the joke of the year.

There was said to be about 200 hours of footage sorted through for this trip and director Josh Greenbaum finds just the right moments to pluck. There’s a lot of vulnerability recognized in both of these figures and their perceptions of each other. While stopping in Texas, Ferrell dons his Sherlock Holmes costume to entertain a crowd as he eats a massive steak in under an hour. Harper sits across from him and she can see the smartphones taking photos and video. She knows what’s coming next. The social media covering this event is going to smear her with transphobia. Will regrets his display, not realizing that he was inadvertently putting a target on his friend’s back. As Harper later relays these hateful posts, she stresses that it’s something that haunts her but not to be downplayed as Will so easily does.

Harper displays vulnerability similarly by taking Will to the very spot where she was at her lowest. But Will’s presence shines some light on the darker moment, where she feels comfortable talking about her suicidal thoughts considering they would evaporate as she transitioned. The support from Ferrell always feels genuine, where he’s doing his best to understand while not coming off obnoxiously progressive. Part of his strategy involves disarming himself, employing his usual goofy tactics of shouting at dogs from a hot-air balloon or assuming a new identity for a fancy dinner. Harper is wise enough to note that this is not the typical manner in which trans people get support, but it has done wonder with her getting more out in the open with herself.

Of course, Will & Harper showcases an earnest portrait of trans allyship, but it’s also genuinely charming and sweet. The ease with which Ferrell can maneuver into jokes that Harper can recognize with an acknowledging smile makes for a great friendship worth documenting. The film is as heartfelt as it is honest, especially for its greater diversity of transitioning when reaching 60. Although Harper has gone through a change, she still has the same humor, the same love of beer that Will despises, and a desire to date again. She’s not aloof to her age and she realizes the clock is ticking, but at least she gets to keep on ticking with Will Ferrell in the passenger seat as he listens, questions, and begs for Dunkin’ Donuts all along the way. The struggle for trans rights doesn’t seem as scary with a devoted friend by your side, something everybody should have and everyone should be.