The pretext of Gail Daughtry is the obvious silliness of the “celebrity sex pass” concept, but the actual joy of the movie comes from unadulterated silliness, full-stop. Like Wet Hot American Summer mocking teenage sex comedies of yore by casting a lot of late 20s and thirtysomethings as camp counselors in 2001—making their encore prequel series shot more than a decade later even more delicious—Gail Daughtry is flush with self-awareness and mirthful absurdity. It’s a movie that begins with Gail Daughtry’s mailman (and stalker?) staring directly into the camera to explain why she is his favorite person in their two-horse town. And like another Kansan who found herself in a magical land, Gail Daughtry’s adventure eagerly becomes about a young woman and her sidekick meeting a collection of enthusiastic helpers and tag-alongs who can think of nothing better to do than aiding in Gail Daughtry’s need to do the deed with the Wizard of Sterling Cooper.
There’s Caleb (Ben Wang), the young and hungry administrative assistant at real-life talent agency CAA. He is only too happy to risk his career and open the company’s files to find Hamm’s local abode; there is also Vincent (Marino), a former paparazzo photographer whose career faded to ashes when he failed to land a photo of AMC’s biggest star 15 years ago; and then of course remains none other than Mad Men co-star John Slattery, brilliantly playing a version of himself as a craven hanger-on who has lost all sense of confidence and identity after Hamm ghosted him by refusing to answer Slattery’s roughly 5,000 texts in the last decade.
If it wasn’t obvious from Gail Daughtry and Otto’s names being virtual anagrams for Dorothy Gale and Toto, this is a literal Tinseltown reworking of The Wizard of Oz, complete with Slattery as the Cowardly Lion. It’s also a love letter to, if not the real-life LA, then that shallow, merrily lascivious version daydreamed by so many tourists fresh off the bus. In fact, Gail and Otto’s own veritable fairy godmother is a concierge at a Hollywood Hills hotel who is thrilled to recommend these yokels to some of the finest local cuisine in the neighborhood (McDonald’s), an authentic artisanal coffee shop (Starbucks), and a back alley where happy endings and dreams really do come true (a crackhead who will do anything for $5 a pop). Ms. Daughtry and Otto cheerfully partake in each of these recommendations during a sprightly montage sequence.
It’s all balanced precariously on the edge between indulgent farce and twee camp, but it never really falls too far in either direction thanks in large part to winsome cast, most especially Deutch. As an actress with oodles of charisma and a game fearlessness when it comes to risking the appearance of inanity, Deutch pours just enough rainbow optimism into the center of the movie to blind out the occasional jokes that don’t work. As with any other mile-a-minute comedy, there are more than a few gags that come and go with nary a chortle, but there are about two bits to every one that hit right in the belly.
Gail Daughtry and Celebrity Sex Pass is slight, frivolous, and more often than not wickedly funny with its navel-gazing mockery of the entertainment industry, inside baseball winks and nods that will play like gangbusters in New York and LA, and its endless parade of actual celebrity cameos and friends whom Wain has cracked open the rolodex of favors for. Look out for his Wanderlust muse Jennifer Aniston in one scene, and Wet Hot American Summer alums Paul Rudd and Elizabeth Banks in others. There is finally that appropriately enigmatic Jon Hamm as the inevitable straight man rock upon whose shores Gail Daughtry and her tidal wave of insanity and sidekicks must eventually crash.
That’s Hollywood hokum at its finest, and fairy dust that will give you a case of the giggles.
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