This guest post is written by Josh Bell.
It’s easy to imagine a more mainstream version of director David Wain’s “Gail Daughtry and the Celebrity Sex Pass,” even one with largely the same cast and creative team. Wain is an alt-comedy titan, but he’s also worked in a more accessible mode on movies like “Role Models” and “A Futile and Stupid Gesture,” and “Gail Daughtry” stars rom-com staple Zoey Deutch as the title character. Even with its self-reflexive premise, it could have been a bland, sweet movie about a woman needing to explore new sexual horizons before realizing that her mundane small-town life and devoted fiancé are exactly what’s right for her.
Thankfully, that’s not what Wain and co-writer Ken Marino deliver. The veterans of iconic sketch-comedy troupe The State come up with a brazenly weird comedy that may be slightly less off-putting than Wain’s 2001 cult classic “Wet Hot American Summer,” but is just as hilarious and just as memorable. With onscreen roles for seven of the 11 members of The State, “Gail Daughtry” is the group’s most extensive reunion in years, and it lives up to the standards for inspired absurdity first set in their 1990s MTV sketch series.
Deutch’s Gail is an upbeat hairdresser in a picturesque Kansas town, where she has everything she could possibly want — or so she thinks. A former cheerleader, she’s set to marry her high school sweetheart boyfriend Todd (Michael Cassidy) and seems to have her whole life carefully planned. But a seemingly harmless indulgence in the thought experiment of the celebrity sex pass sets her on a very different path.
The sheltered Gail has never heard of the idea of couples giving each other a theoretical free pass to have sex with one celebrity of their choosing, should the opportunity arise, but she’s intrigued when her co-worker and best friend Otto (Miles Gutierrez-Riley) explains it to her. She’s so wholesome that she initially declares that former star quarterback Todd would be her celebrity sex pass. Todd, however, takes the game a bit more seriously, impulsively choosing Jennifer Aniston as his potential famous fling when they attend a reading of Aniston’s new cookbook.
Aniston’s self-deprecating cameo, reading aloud from a book of bland, basic recipes, is the first of many such appearances from celebrities as themselves, but “Gail Daughtry” isn’t just about how many famous people Wain has listed in his contacts. Wain and Marino use their high-profile guest stars as building blocks for the story, starting with Todd following through on his sex pass with Aniston, right in the staff lounge of the bookstore where she has her reading.
Mortified that her fiancé has cheated on her, Gail leaves Kansas for the first time to join Otto at a hairstyling convention in Los Angeles, where a psychic tells her that the only way for her to get even with Todd and restore balance to their relationship is to seek out and bang her own celebrity sex pass: Jon Hamm. It’s a patently ridiculous quest that Gail approaches with single-minded determination, convinced that it will solve all of her problems, and assuming that anyone who understands her motivations will immediately want to help her.
Improbably, that mostly turns out to be true, and Gail and Otto amass a crew of supportive accomplices as they travel across the city in search of Hamm. Wain and Marino take narrative cues from “The Wizard of Oz” and “Pee-wee’s Big Adventure,” with each new encounter garnering Gail and Otto new friends who bring them incrementally closer to their goal. That eventually includes anxious agent-in-training Caleb (Ben Wang), washed-up paparazzo Vincent (Marino), and Hamm’s “Mad Men” co-star John Slattery, playing a version of himself who hasn’t had an acting gig since the hit drama ended production.
Slattery creates what may be the best version of a celebrity piss-take role since Neil Patrick Harris’ appearances in the “Harold & Kumar” movies, as a desperate, needy loser who’s also surprisingly adept at hand-to-hand combat. That comes in handy thanks to the movie’s other major storyline, in which Gail is pursued by a pair of mobsters whose all-important briefcase she accidentally swapped with her own at the airport.
Joe Lo Truglio and Mather Zickel are amusing as the put-upon henchmen of a megalomaniacal Italian criminal mastermind (Sabrina Impacciatore), but the movie is crazy enough that it doesn’t need an additional subplot about a dangerous terrorist attempting to destroy the world’s financial systems. As he did in his Netflix prequel and sequel series to “Wet Hot American Summer,” Wain seems intent on adding life-or-death stakes to his goofy comedic scenarios, as if he doesn’t quite trust the audience to stay invested in the low-key insanity.
The crime plot pays off with a climactic confrontation full of exaggerated violence worthy of a Sam Raimi movie. But the funniest moments in “Gail Daughtry” are the more mundane, often inexplicable running jokes, like Gail’s hometown mailman (Fred Melamed) narrating the story out of a sense of grudging obligation, or Hamm’s bodyguard repeatedly threatening to make Gail and her friends “very sick” if they don’t back off.
Wain gets excellent results from his entire cast, whether that’s his longstanding collaborators from The State, or newcomers to his work like Deutch and Wang. Deutch plays a minor variation on her likable rom-com persona from movies like “Set It Up” and “Everybody Wants Some!!,” making Gail charming but just a little off, and letting the supporting cast play up their broader characters. Wang, who’s best known as the star of the abysmal legacy sequel “Karate Kid: Legends,” redeems himself with an understated oddball performance as Caleb, a clearly inept talent agent who’s always talking about his “mommy,” but is also resourceful when it counts.
When he finally shows up, Hamm plays the same handsome doofus he’s honed in multiple comedies, doing exactly what’s expected of him without making the same comedic leap as Slattery. Wain keeps all of these performers expertly balanced, and “Gail Daughtry” rarely has the episodic feel that can plague too many feature films from sketch comedians. It’s Wain’s best film as a director since “Wet Hot American Summer,” and maybe the first to truly synthesize The State’s surrealist sensibility and the crowd-pleasing aims of fellow State alum Michael Showalter’s directorial efforts (including “The Big Sick” and “The Idea of You”).
Wain’s films may never reach as wide an audience as Showalter’s, but that means he’s able to retain a more distinctive artistic vision. It’s not hard to imagine a more mainstream version of “Gail Daughtry,” but it’s impossible to imagine that this version could have been created by anyone else.
Image Credit: “Gail Daughtry and the Celebrity Sex Pass”
