Documentary Review: “Will & Harper” take a Road Trip to test America’s Transgender Tolerance

What was “the pitch” for “Will & Harper” like?

This road trip documentary about two longtime friends and colleagues getting together after one has transitioned is sweet as can be, but it’s “showbiz” all the way. Will Ferrell met Andrew Steele when they joined “Saturday Night Live” at the same time. One became perhaps the greatest star the sketch comedy series has ever produced, the other a writer who became head writer of the show.

After “SNL,” Ferrell starred in such Steele-scripted comedies as “Casa de mi Padre” and “Eurovision Song Contest: The Story of Fire Saga,” and they collaborated on the comedy website “Funny or Die.”

Ferrell tells us and shows us how he learned of his friend’s transition from Andre to Harper and accepted it.

But whatever the pitch or intent of what is, in essence, a documentary version of 2005’s “Transamerica,” this “put two funny friends in a car to see revisit America after one has come out as a woman” road picture becomes a sociological experiment.

How tolerant is this country, where a whole class of politicians and preachers has made hating transgender people a brand, rallying bigots far and wide?

As Steele, under her “dead name,” has long loved doing what writers do, hitting out of the way bars, diners, sporting events and the like, “meeting people,” listening to them, plumbing for ideas, “characters” and dialogue, how will that work with her in a dress and an assortment of not-quite-Dame-Edna glasses?

Where will she be accepted, and where won’t she?

How much “s–tty beer” (Steele’s lifelong love of “Natty Lite” is rightly mocked) and how many varieties of Pringles chips can two friends consume as they motor cross country to conduct this study?

And whose vintage Jeep Wagoneer is Harper driving when she picks Will up in Van Cortlandt Park in the Bronx? It’s implied it’s Harper’s, but it has California plates. Is it Will’s? A properly “butch” classic rental for a gender-bending road trip?

Ferrell, whose “nice guy” bonafides are polished to a fine sheen here, is a surrogate for the audience in asking all the “s–tty questions you’re not supposed to ask people.” Harper welcomes this chance to deliver public service announcements in the basics. And being funny down to his bones, Ferrell finds the laughs.

On “boobs” — “Did you go to Nordstrom’s Rack once you got your rack?”

“Do you think you’re a worse driver as a female driver?”

Steele, whom Ferrell met as an “Iowa born, 501 jeans and s–tty beer” comic, never really comes off as all that funny, at least in this situation. She frankly admits that her life (formerly married, two kids) and the TV comedy writing career she had would not have happened had she transitioned sooner than her 60s. Tina Fey excepted, comedy writing has been by and large a “bro’s” game.

On their mid-winter trip, they’ll meet Harper’s two daughters, only one of whom is identified by name while the other invites questions left unanswered. They visit D.C. and Indianapolis for a Pacer’s game, accidentally meeting the state’s latest homophobic governor, unknowingly posing for “the photo you don’t want to be in.”

They’ll hit Harper’s hometown, Iowa City, stop in Oklahoma and Texas, at a car race and a honky tonk decorated with Confederate and Trump flags and worse, and a Texas steakhouse where Ferrell dons a Sherlock Holmes costume to compete in the “72 ounce steak is free if you can eat it in an hour” challenge.

Ferrell will also don a “disguise” that too closely resembles his “Zoolander” hair and costume to truly fool a Vegas waiter or anybody else.

And America, perhaps acknowledging the friend, relative or child, or friend or relative’s child we all know who transitioned, is for the most part polite and even accepting. Waiters and waitresses correct their “sir” to “madame,” and so on.

But on social media, where we’re at our meanest, a lot of those people taking selfies and cell shots and videos (even on the residential street where Harper’s Iowa City sister lives) take the time to share their online ignorance and their bigotry.

Steele is rattled, here and there. And Ferrell, who jokes around with his “celebrity” most of the time, has a few upsetting moments where he truly appreciates what his friend has gone through and is now subjected to and the dangers transgender people face in much of America.

We and he come to appreciate the role celebrity has in disarming such intolerance.

Whatever the original pitch to Netflix, “Will & Harper” became a hopeful, upbeat snapshot of a nation struggling with its own transition, just a couple of pals in a collectible Jeep, experiencing the “real” America — diners, dives and Walmarts — and the wide array of folks who inhabit it, at least some of whom are starting to “get it.”

Rating: R, profanity, adult subject matter, lite beer consumption

Cast: Will Ferrell, Harper Steele, Tina Fey, Will Forte, Tim Meadows, Molly Shannon, Seth Meyers and Kristen Wiig

Credits: Directed by Josh Greenbaum. A Netflix release.

Running time: 1:51

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About Roger Moore

Movie Critic, formerly with McClatchy-Tribune News Service, Orlando Sentinel, published in Spin Magazine, The World and now published here, Orlando Magazine, Autoweek Magazine
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