Wicked may have reimagined The Wizard of Oz as a saga of open-mindedness, adversity, and companionship, but it was (relatively) light in the sex department.
Gail Daughtry and the Celebrity Sex Pass makes up for that shortcoming, using L. Frank Baum’s legendary tale as a template for an absurd story about a sweet and naïve Midwestern girl who embarks on an epic quest of self-fulfillment in which she makes new friends and battles evil foes on her way to see a very important man.
In this case, that man is Jon Hamm... whom she must screw.
Writer/director David Wain’s first film since 2018’s A Futile and Stupid Gesture—and his latest to premiere at the Sundance Film Festival—Gail Daughtry and the Celebrity Sex Pass is a fable about Gail Daughtry (Zoey Deutsch), a preternaturally sunshiny resident of Willowbrook, Kansas. Gail has never left the state, is engaged to her high school sweetheart Tom (Michael Cassidy), and does hair at the local salon alongside BFF Otto (Miles Gutierrez-Riley), who’s planning to travel to Los Angeles to attend a hair styling expo featuring “king of the whip curl” Remy Fontaine (Thomas Lennon).
At work one day, Gail learns about the concept of a “celebrity sex pass”—i.e., an agreement between partners regarding the one famous person they can cheat with—and though she says she’s not interested, she and Tom do admit that their choices would be, respectively, Tilda Swinton and Hamm.
What begins as an innocuous conversation turns very real when, following the couple’s attendance at a Jennifer Aniston book signing, Tom decides that the Morning Show actress would actually be his celebrity sex pass—and then promptly acts on it, much to Gail’s shock and dismay.
In response, she joins Otto on his weekend getaway to L.A. At the airport, mere moments after arriving, Gail has her first run-in with a screen star: Henry Winkler, who’s asked for a picture by two men in matching suits, Sergio (Joe Lo Truglio) and Tomasso (Matthew Jayson Cwern).
The Man Who Was Fonzie is happy to oblige, but during this photo opportunity, they place their briefcase beside Gail’s identical haircare case, leading to a switcheroo that subsequently infuriates the duo’s Wicked Witch-y gangster godmother (The Paper’s Sabrina Impacciatore), who needed its contents to fulfill her dream of destroying the global financial system.
This is a rather stale set-up, and Sergio’s attempts to reclaim his boss’ valuable merchandise prove a humorless subplot that can’t even feign urgency—and thus primarily comes across as Wain and co-writer Ken Marino’s means of providing their pal Lo Truglio with a role.
He’s not their sole friend who pops up in these cameo-rich proceedings; at various points, their The State and Wet Hot American Summer mates Michael Ian Black, Kerri Kenney-Silver, and Elizabeth Banks (among others) factor into the proceedings, albeit in ho-hum parts that feel like favors and fail to capitalize on the comedians’ absurdist strengths.
Gail’s Winkler sighting isn’t the last time she bumps into a well-known actor; her cab driver, for instance, is Richard Kind, who single-mindedly prattles on about Elizbeth Perkins. Gail’s main goal, however, is to locate and sleep with Hamm, which she believes will make her and Tom even and allow her to get past his infidelity and proceed with their wedding.
In this expedition, she’s aided by a Star Maps street vendor (Black) who points her to Creative Artists Agency. There, aspiring agent Caleb (Ben Wang), sympathizing with Gail’s mission, tries to procure Hamm’s address, only to get fired and become the unofficial third member of Gail and Otto’s crew.
The trio’s search leads them to the home of “Weird” Al Yankovic, where they run into paparazzo Vincent (Marino), who claims that he was once so good at his job (at People magazine) that he was known as “Mr. Always Gets His Shot Even When It’s a Hard Shot to Get.”
Yet the one luminary he never snapped was Hamm, his “white whale.” He too tags along, pointing Gail in the direction of the actor’s Mad Men co-star John Slattery, whose zealous fight training hasn’t made him any less courageous—he pukes at the first sign of violence—and who agrees to help Deutsch’s protagonist bed her target.
Skipping arm-in-arm down the street like Dorothy Gale (get it?) on the Yellow Brick Road, the blue-dressed Gail is a naïve and upbeat protagonist who’s game for mayhem, and Deutsch’s performance is likably cheery. The film fires off jokes at a rapid clip, but its aim is poor, and as the mirthless one-liners accumulate, it begins to resemble a collection of sketchy incidents in need of additional rewrites.
Whereas the best examples of this comedy form frequently feature end-credits outtakes which indicate that hard work went into devising the best quip possible, Gail Daughtry and the Celebrity Sex Pass gives the impression that everyone settled on their first idea.
Visually speaking, Wain has never been more than a functional director, but at least a few of his prior films were snappy. His latest, in comparison, is a languid affair that only intermittently strikes inspiration, as when Hamm’s bodyguard (Tobie Windham) threatens to make Gail and company “sick” and then ceaselessly slams the door on Slattery’s foot.
More frustrating, by making Hamm the story’s obvious destination, his eventual appearance is too predictable to be amusing. And though Fred Melamed’s mailman is an unexpected and witty narrator, he’s criminally underutilized.
Gail Daughtry and the Celebrity Sex Pass makes subtle early references to The Wizard of Oz before transforming into a veritable riff on the fantasy classic. Yet the parallels are often strained and halfhearted, and awkward to the point of being cringeworthy.
If my math is correct, Lo Truglio and Mather Zickel’s Italian henchmen are the flying monkeys, and Gutierrez-Riley’s Black gay Otto is the material’s Toto. Trying to parse such links, however, isn’t worth the effort, since Wain and Marino don’t seem to have cared enough to tighten them up.
Consequently, there’s not much to latch onto here except the faint flickers of the better film this one, with more care and attention to detail, might have been.
