From Wet Hot American Summer’s lampoon of early-’80s sex comedies to They Came Together’s send-up of rom-coms, David Wain is no stranger to broad, absurdist genre spoofs. With Gail Daughtry and the Celebrity Sex Pass, which he directed and co-wrote with frequent collaborator Ken Marino, Wain has narrowed his scope somewhat with a retelling of The Wizard of Oz that doubles as a skewering of Hollywood.
Mere days before their wedding, Kansas-bred Gail (Zoey Deutch) discovers that her fiancé, Tom (Michael Cassidy), took advantage of his celebrity sex pass by sleeping with Jennifer Aniston in Los Angeles. This causes the hairdresser to spiral and try to sleep with her celebrity crush, Jon Hamm. That premise doesn’t immediately invite comparison to The Wizard of Oz, but the film is chockablock with references to L. Frank Baum’s Oz books and its various adaptations.
Once Gail and her bestie, Otto (Miles Gutierrez-Riley), touch down in L.A.—and to the accompaniment of an aspect ratio change that references Oz the Great and Powerful—they assemble a ragtag team of Hollywood losers who map cleanly onto Dorothy Gale’s companions. Ben Wang’s Caleb, a failed talent agency assistant, is the Scarecrow; Marino’s Vincent, a paparazzo who’s lost his conviction and morals, is the Tin Man; and John Slattery, who, as himself, talks a big game without the courage to back it up, is the Cowardly Lion.
Each of these individuals joins Gail out of compassion for her ordeal, and a belief that meeting Jon Hamm will transform them into better versions of themselves. It comes as no surprise, then, when the actor eventually turns out to be a man of smoke and mirrors, so to speak, failing at first to deliver on any of the promises he makes to Gail and her friends.
More than a substitute for the Wizard of Oz, Hamm is a stand-in for every outsized celebrity who’s emboldened by Hollywood. That’s not an especially novel concept, but Wain and Marino delight in hammering the point with zealous comic bluntness. Gail Daughtry and the Celebrity Sex Pass is about the rose-colored glasses through which people like Gail view Hollywood, and the film contrasts her optimistic perspective with its less than glorious visual treatment of Tinseltown. Occasional cutaways to iPhone footage, low-res drone shots during scene transitions, and even the occasional sequence captured on overexposed GoPro paint a vulgar digital portrait of the city that a simply-happy-to-be-there Gail isn’t attuned to.
But the film’s main mission isn’t to deliver a postmodern treatise on the state of Hollywood, à la David Lynch’s Mulholland Drive, but rather a self-consciously absurd, irreverent comedy. Gail Daughtry and the Celebrity Sex Pass is basically a steady stream of gags and utter ridiculousness, and in that regard, it mostly throws softballs. The majority of jokes boil down to simply invoking the premise—though Deutch’s spirited balance of Midwestern naïveté and blunt sexual conviction adds considerable mileage to that—and winking at us over how nonsensical it is to be borrowing so heavily from The Wizard of Oz in the first place. While it doesn’t hold a candle to past Wain comedies with higher hit-to-miss ratios, there’s an underlying warmth to the film that cuts through its disillusion with the industry that created it.
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