Director Josh Greenbaum was known as a documentary filmmaker before he shifted gears for “Barb and Star Go to Vista Del Mar,” and with “Will & Harper” — a nonfiction buddy comedy in which Will Ferrell drives across the country with a beloved colleague — he returns to his nonfiction roots in order to confront a series of questions that seem as far from his comfort zone as they are from Ferrell’s. Questions like: How does a straight cis male of a certain age come to terms with the fact that one of his oldest friends has just come out as trans? And what will happen to their friendship when said trans woman refuses to stop for donuts? (Spoiler alert: Ferrell has a comic meltdown, declaring the whole trip “stupid” if he doesn’t get his Dunkin’).  

Of course, the more important character in this story is the much less famous — if equally titular —  Harper Steele, the Emmy-winning “SNL” senior writer behind such gonzo Ferrell efforts as “EuroVision Song Contest: The Story of Fire Saga.” Having come out in her 50s, the sardonic Harper is now touchingly unsure how to navigate the once-familiar cis male world as her new authentic female self. That’s daunting enough in New York City, but what about in her Iowa hometown or deepest Texas? Fortunately, Harper has an enthusiastically supportive pal who loves beer and rural dive bars as much as she does, and he’s up for road-tripping through kitschy flyover state venues from coast to coast.

Despite being a big fan of Will Ferrell’s, I couldn’t help but wish that Harper’s friend had been John Waters, and that the film had been helmed by a trans director like Zackary Drucker instead of someone who accentuates the supposed novelty of the situation. For while “Will & Harper” has moments both poignant and laugh-out-loud funny (a hot air balloon scene in Albuquerque is genius, and lifted even higher by a cameo from Will Forte), Greenbaum’s filmmaking is often far too reticent, as he tends to play things “straight” and take pains not to offend. Admirable and understandable as that might be, it leaves “Will & Harper” trapped in a mushy middle state, forever prevented from rising to the level of either great drama or great comedy.

And when the setups do venture out from timid territory they sometimes end up backfiring spectacularly. Case in point: A clunky scene that takes place at a Texas BBQ joint sponsoring a steak-eating contest. Inexplicably, Ferrell decides to enter — both the restaurant and the contest — attired in his Sherlock Holmes costume, accompanied by Harper, who’s dressed demurely as herself. When that predictably (and literally) puts the spotlight on Ferrell and his companion, it brings out the smartphone cameras, which in turn allow the footage to be shared online and feasted upon by an army of perpetually online transphobic trolls. It’s a case where throwing chum to sharks isn’t the best idea.

Indeed, watching that pointless uncomfortableness unfold left this genderqueer viewer simply scratching my East Coast-liberal head and surprised to find myself sympathizing with the equally confused right-wing Texans to a certain degree (I guess that’s one way to bridge a divided country). If a comedian walks into a restaurant decked out as a Victorian-era detective with a trans woman by his side, is it really that farfetched to assume his companion might be part of a joke that, frustratingly, no one else in the room is in on? Ferrell, for his part, is deeply upset by and sorry for putting Harper through that ordeal, which is no doubt heartfelt. That said, prompting conservatives to question whether a trans individual is part of a Borat-style statement/stunt designed to make fun of them is not a path to enlightenment — it’s a wringer that a fragile newbie to queerdom should never have to be put through.

Regardless, it’s rather simplistic to assume these Lone Star denizens are simply reacting in horror to a trans person’s presence. If Ferrell and his female sidekick had walked in and sat down as regular folks with little fanfare, I’m guessing they would have been met with the same collective shrug they elicited in the Oklahoma honky tonk bar where a young cis male sweetly tells Ferrell how nice it is of him to support his friend. Instead, the scene finds them being targeted by the usual opportunists who ride social media coattails from NYC to LA — a crowd desperate to be seen, and to escape their own unhappy skin.

Grade: B-

“Will & Harper” premiered at the 2024 Sundance Film Festival. It is currently seeking U.S. distribution.

Leave a comment