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David Wain’s ‘Gail Daughtry and the Celebrity Sex Pass’ Delivers Jolt of Anti-Reality Comedy

Stupid comedy? That's where it's at.

Gail Daughtry and the Celebrity Sex Pass cast

Gail Daughtry and the Celebrity Sex Pass
Writers:
Ken Marino, David Wain
Director: David Wain
Cast: Zoey Deutch, John Slattery, Ken Marino, Miles Gutierrez-Riley, Ben Wang, Sabrina Impacciatore, Jon Hamm


Yeah, smart comedy’s nice and all, but stupid comedy? That’s where it’s at. Give us your dick jokes, your fart gags, your self-aware-yet-wholly-oblivious meta one-liners that do not break the fourth wall as much as they affix to it a brick of C4; the dumber the better, because when you’re wisecracking from the bottom of a barrel, the only way to go is up. Arguably no director of contemporary comedy understands this better than David Wain, whose work on screens both big (Wet Hot American Summer) and small (The State) has influenced Gen X as well as Millennial humor, and whose new film, Gail Daughtry and the Celebrity Sex Pass, evinces his revitalization for sheer LPMs (laughs per minute).

If you live in a pocket of the U.S. where sex is a thing you do through a hole cut in your bedsheets, and only for the sake of being fruitful and multiplying: a lesson. People, as in “people who are freaks in healthy, sex-positive ways, rather than in puritanical, creepy ones,” like to keep handy a list of celebrities they’d smash if fate afforded them a chance and consent; Gail Daughtry (Zoey Deutch), Wain’s plucky, guileless heroine, is one such person, a woman so sweet she’d give an Oreo a toothache. She’s head over heels for her white bread fiancé, Tom (Michael Cassidy), who reciprocates the feeling in their treacly interactions together. And hey: why not? They’re almost newlyweds, counting down the days ‘til they tie the knot. 

Harmlessly, or so the couple thinks, they each share with the other their celebrity crush; Tom hastily names Tilda Swinton (though she’s a solid pick, no doubt), while Gail hops in line with half of all American women (and a profound chunk of American men, too) with a claim on Jon Hamm. Again: harmless! Then Jennifer Aniston comes to town for a book signing; Tom changes his pick; and before Gail, Tom, and frankly Aniston know it, the latter two are making “friends” on a retail shop’s couch. Gail understandably feels a smidge betrayed. So she does what any normal spurned bride-to-be would do: she hops a flight to Los Angeles to even the score by tracking down and banging Hamm.

The task Gail lays at her own feet is one part easy, another part Herculean. Convincing Hamm to fold her in half like a Sterling Cooper Draper Price pitch board is as easy as breathing; actually tracking Hamm down and securing an audience with him is, on the other hand, much harder. Wain gives her a helping hand by lifting from the best, being Victor Fleming, and structuring Gail Daughtry and the Celebrity Sex Pass as a riff upon The Wizard of Oz. Hint: Gail is Dorothy. Her bestie, Otto (Miles Gutierrez-Riley), is the film’s Toto; its Cowardly Lion is John Slattery, playing John Slattery, if you can accept a fictionalized version of John Slattery to whom life has been unkind post-Mad Men; its Scarecrow is Caleb (Ben Wang), a jittery mama’s boy working at CAA, the talent agency repping Hamm; and its Tin Man, by process of elimination, is Vincent (Ken Marino), a disgraced paparazzo, oxymoronic as that sounds. Together, they embark on a journey to meet Hamm, because surely that’s all it’ll take to get him and Gail to bang.

There’s not much stuck to Gail Daughtry and the Celebrity Sex Pass’ bones apart from its joke volume, but generally speaking, a comedy must be funny above everything else. A stand-up who rants-by-numbers about the American political system isn’t performing comedy, but rather punditry; a filmmaker is as vulnerable to making the same tiresome miscalculation. Wain isn’t that filmmaker. If there’s a complaint to hold against him and against Gail Daughtry, it’s the sensation that he and Marino wrote the script as a reason to invite their friends over to hang out. Familiar faces abound: Joe Lo Truglio, Thomas Lennon, Kerri Kenney-Silver, Michael Ian Black, Beth Dover. There are, however, worse reasons for films to get made than a pal reunion, these pals most of all, who have known each other, and worked together on and off, for so long that they’re simpatico to a nearly psychic degree. 

Deutch, Wang, and Gutierrez-Riley are the odd ones out, as the case may be–everyone’s odd in a Wain movie–and that’s to Gail Daughtry’s benefit. For one thing, Deutch is an actor tragically born in the wrong era; if we still made movie stars, or if movie stars even mattered anymore, she’d be one of our brightest. Whatever she does, whatever film she’s in, Deutch manages the balancing act of being wholesomely agreeable and abandoned at the same time. Her ease before the camera would be unsettling if it wasn’t so charming. For another thing, she’s complemented in her natural ease by her supporting cast, Wang especially, playing Caleb as a schlemiel figure whose bundle of neuroses enjoy throwing him surprise parties. There’s a sense that the film’s younger trio of protagonists, backed by the veterancy of Marino and Slattery, provided Wain with a spark during production, a necessary jolt of newness in his well-established troupe and fundamental aesthetic; it’s possible he’s been searching for that element in the intervening years between today and his second Wet Hot American Summer reprisal back in 2017.

On the other hand: maybe not. Also, who cares? Gail Daughtry and the Celebrity Sex Pass encapsulates what’s great about snappily paced anti-reality comedy, and as such, what’s great about Wain as a director of said comedy: at no point will you learn much of anything profound about the human spirit, at least not until a few days after you watch the movie and have caught your breath for long enough to consider, for instance, how real it is that an inexperienced Kansan hairdresser would realize her unworldliness only after catching her future husband casually nailing Rachel Green. 

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