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This week, we’re bringing you a special episode from Revisionist History, Malcolm Gladwell’s podcast about things overlooked and misunderstood. Gladwell’s show recently investigated what was once the biggest secession movement in the US since the Civil War: the movement by disillusioned residents in Staten Island to secede from New York City. Subscribe to Mother Jones […]

Thirty years ago, on a not very special episode of Friends (“The One With Frank Jr.,” for the record) Ross and Rachel swapped “Celebrity Freebie” lists: top fives of famous people with whom they would each choose—and be allowed by their partner—to have consequence-free sex. Ever the culture vulture, Ross opted for Isabella Rossellini, leading to the most incongruous Blue Velvet shout-out in prime-time history. Rachel, meanwhile, chose Chris O’Donnell, John F. Kennedy Jr, Daniel Day-Lewis, Sting, and, in a shocker, ex–Hardy Boy Parker Stevenson. The heart, it has been said, wants what it wants. David Wain’s new film, Gail Daughtry and the Celebrity Sex Pass, turns on an egregious no-strings-attached mishap, complete with a cameo from the erstwhile Ms. Green. The setting is Wilbur, Kansas, all picket fences and strip malls, where former high school sweethearts Gail (Zoey Deutch) and Tom (Michael Cassidy) are set to be wed. She’s bubbly and sweet, beloved by her neighbors and beauty parlor clients; he’s gormless and visibly out of his depth. Both are seemingly happy to go through the motions till death do them part. Pregaming an author event at their local bookstore, Gail and Tom start hypothesizing about their celebrity freebies; since the writer in town for the signing is Jennifer Aniston—there to hawk a no-frills cookbook of “Sensible Suppers”—they both agree that she’d be a suitable fantasy fling. Cut to Tom in flagrante delicto a few hours later in the back of the store with America’s Sweetheart. “We talked about this,” he pleads to Gail, who’s mortified, as is Jennifer, which doesn’t stop her from arranging to send Tom some DVDs of Friends (he only knows her from The Morning Show). Heartbroken, but determined to get even on her own set of ethical terms—and egged on by her standard-issue sassy best pal, Otto (Miles Guttierez-Riley)—Gail puts her game face on. Otto is off to Los Angeles for a hairdressing convention and suggests she tag along. Their target: Jon Hamm, a handsome prince ensconced at the Chateau Marmont.No sooner have Gail and Otto landed at LAX than they’ve caught a cab ride with Richard Kind, obtained some star maps, and learned about the best spots in town to get a burger (McDonald’s), a coffee (Starbucks), and a blow job (Foot Locker). They also accidentally obtain the briefcase of a reigning Mafia queen bee (Sabrina Impacciatore) who has designs on bringing down the global financial system and is willing to kill the strangers who’ve made off with her documents. Other impediments to Gail’s righteous carte blanche booty call include misfiring hitmen, unctuous personal assistants, and a machine-gun-toting “Weird” Al Yankovic, who helpfully tells her and her friends to “eat it” while chasing them off his property.David Wain does not make realistic, or even halfway plausible, movies. This laxity is his badge of honor,  and he wears it well. Suffice it to say that Wain, who once cast Aniston opposite Paul Rudd in 2012’s Wanderlust, does not make realistic, or even halfway plausible, movies. This laxity is his badge of honor, and he wears it well. Where a status-climber like Judd Apatow cultivates a strenuous, and largely disingenuous, naturalism—John Cassavetes by way of SNL—Wain has no use for respectability. He’s yet to abandon the slovenly, see-what-sticks shtick of Wet Hot American Summer (2001), an epochal work that has informed a swath of postmillennial alt-comedy. By sticking to his guns—and also letting them misfire, or shoot blanks—Wain runs the risk of seeming like an inept veteran, when he’s actually an old master of his very particular chosen form. Gail Daughtry and the Celebrity Sex Pass is not a good-looking movie: Kevin Atkinson’s cinematography is so hypnotically bland that Main Street USA and the Inland Empire become virtually indistinguishable from one another. The performances are broad to the point of active mugging; the storyline doesn’t so much strain continuity and credibility as leave them to bleed out in a ditch. This is all to the good. Wain and his co-writer, Ken Marino, who appears as a veteran paparazzo helping Gail navigate the City of Angels, have each worked on plenty of “normal” television and streaming series since their days on MTV’s The State. They’ve had successful careers meeting the industry halfway—especially Marino, who’s usually the funniest part of whatever he’s in. What they refuse to do is make compromises on their own time. Instead, they play a game of (rubber) chicken with themselves and the audience, torquing artificiality and contrivance into its own screwily lucid sort of worldview: a wryly complacent gaze into the pop-cultural abyss. Wain is often called a satirist or a parodist, which is true for instance of the winking, ruthless Nora Ephron–esque They Came Together (2014), which leaves vintage rom-com tropes to ripen and rot on the New York City pavement. The label doesn’t always fit, however. “I don’t consider Wet Hot American Summer a spoof at all,” Wain told The Film Stage; “it’s just a movie really sourced in actually going to summer camp, and it’s funny.” The skeleton key to unlocking the director’s sensibility—not that it’s necessarily airtight in the first place—might just be Wet Hot’s gee-whiz, summer-stock metaphysics—the wholesome, theatre-kid excitement of getting your friends together and putting on a show. Think of the wonderfully sincere sequence where a group of preteens perform “Day by Day” from Godspell, an almost enchanted interlude that feels plucked from memory. And then there’s the final act of Wain’s deceptively conventional and Apatow-adjacent 2008 masterpiece Role Models (co-written with Marino), in which the protagonists are finally reconciled by a rousing game of Medieval cosplay—an immersion in nerd culture enacted with a welcome lack of condescension toward characters and audience. It makes sense that such an inveterately playful filmmaker would finally get around to riffing on The Wizard of Oz: Victor Fleming’s 1939 classic is the primal scene of Hollywood escapism, after all. The sheer slack-jawed obviousness of the references here is part of the point: “Gail Daughtry” inverts “Dorothy Gale” as surely as “Otto” scrambles “Toto,” and Hamm eventually refers to himself as a wizardly “man behind the curtain.” Within the film’s Emerald City framework, John Slattery, playing a B-list celebrity, serves as a modern version of the Cowardly Lion (“Put ’em up, put ’em up,” he mumbles, shadowboxing in his garage). Ben Wang, playing a Creative Arts Agency rookie, is a scatter-brained Scarecrow manqué, and Marino as the cynical, heartless photographer has shades of the Tin Man. Slattery’s performance is wonderfully unhinged; he’s funniest when he’s being used as a punching bag, whether rhetorically—as in an uproarious series of text messages narrating his incremental estrangement from Hamm (who’s left his buddy on read for several years)—or literally, as when he gets a hotel room door slammed on his ankle 34 times, each jolt punctuated by its own piercing yelp of “Ow!”There is a fine line between liberated and lazy, and Gail Daughtry refuses to pick a lane on principle.David Lynch used to suggest that most of his movies were spiritual remakes of The Wizard of Oz, and Wain’s embrace of low-rent surrealism can feel Lynchian at times; by following a guileless ingenue through a freaky version of “Hollyweird,” Gail Daughtry becomes the director’s Mulholland Drive, right down to the script’s winking anxiety about the perils of show-business-as-usual. There aren’t a lot of comedy directors who are so willing to deal in outright alienation effects, like the repetition-compulsion of Slattery’s battle with the door, or the gratuitously brutal violence of a late action sequence seemingly staged in one of the same locations as Quentin Tarantino’s Once Upon a Time in Hollywood. And then there’s the narrator, played by the honey-voiced character actor Fred Melamed, who starts out cheerful and folksy about Gail and her friends but begins wearying of the WTF nature of the material around the same time we do. Melamed’s descent into raging dyspepsia is a signal that Wain knows very well he’s wasting his—and our—time and trusts that we don’t mind. There is a fine line between liberated and lazy, and Gail Daughtry refuses to pick a lane on principle. The swerving is the point; the pleasure resides in the high-minded notion—rooted in the golden rule of improv—that all jokes, including and especially the bad ones, are created equal. It’s hard to reconcile deliberately half-hearted humor with real emotion, and Gail Daughtry and the Celebrity Sex Pass is deliberately underwhelming both as a love story and as an attack on the culture industry. Wain loves his offhand anticlimaxes; no surprises for guessing that, choosing between a cheating dork on the one hand and Don Draper on the other, our heroine finally chooses herself. But Gail’s parting words sum up the movie, its makers, and their passions so nicely that they bear repeating. “Let’s keep it loose and freaky,” Deutch tells Hamm before they float off together in a hot air balloon, somewhere over the rainbow.

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