A deliriously funny riff on The Wizard of Oz from director David Wain, Gail Daughtry and the Celebrity Sex Pass is a goofy patchwork of ideas. Some of them don’t work, but most of them do if you’re in on the joke. Written by Wain and his longtime collaborator Ken Marino, the comedy features an incredible number of hilarious people, sometimes playing absurdist versions of themselves. Jon Hamm, Jennifer Aniston, John Slattery, and Elizabeth Banks, among others, cameo alongside a cast of lesser-known but no less talented performers. Headlining the movie is Zoey Deutch, who, amid an impressive list of credits, has proven her knack for ridiculous humor like this (see 2019’s Zombieland: Double Tap). Wain directs a series of episodic segments that follow characters who skip along a yellow brick road of surreal gags and jokes about Hollywood. It’s all a bit nonsensical and ludicrous, but it made me laugh a lot.
For those of us who loved MTV’s sketch-comedy show The State (1993-1995) or Wain’s spoof movies such as Wet Hot American Summer (2001) and They Came Together (2014), Gail Daughtry will feel like a warm blanket. The State was a comedy troupe nesting ground for talent, many of whom went on to create and appear in dozens of other shows (Viva Variety, Reno 911!, Childrens Hospital, etc.), while member Michael Showalter has become a well-respected director whose output includes the indie comedy The Big Sick (2017) and the upcoming Colleen Hoover book adaptation Verity. Whenever Wain and Marino reteam with various members of The State (Michael Ian Black, Thomas Lennon, Kerri Kenney-Silver, Joe Lo Truglio, et al.), there’s usually something special in store. Even if the material doesn’t always work as a whole—see The Ten (2007), an anthology movie that pokes fun at the Ten Commandments—the result is bound to include some big laughs.
Deutch plays the titular Kansas bumpkin, a hairdresser who plans to marry her fiancé and lifelong sweetheart, the ingeniously named Tom Soursap McNoodleman (Michael Cassidy), in two weeks. At once naive and intense, she’s never been with anyone else. Neither has Tom. But after sharing their picks for a celebrity sex pass, Tom almost instantly encounters his choice in the flesh and then takes advantage of the opportunity. Burned because she didn’t actually think they were serious about following through, Gail resolves to seek out her chosen celebrity, Jon Hamm, and have sex with him to balance the scales. And so, Gail is off to see The Wonderful Wizard of Hollywood, alongside her coworker named Otto (Miles Gutierrez-Riley), an anagram of Toto. As the story unfolds, Gail Daughtry spoofs the structure of Dorothy’s adventure to Oz, except that Gail’s destination is Tinseltown.
Just as New York was “another character” in They Came Together, Los Angeles becomes one here. But instead of capturing the city’s flavor, Gail and Otto gravitate toward CityWalk at Universal Studios and, based on their hotel concierge’s recommendations, other local hotspots such as McDonald’s, Starbucks, and 7-Eleven. Gail and Otto begin searching for Hamm and gather friends along the way. Among them are Vincent (Marino), a former paparazzo who dreams of snapping a photo of Hamm; Caleb (Ben Wang), an aspiring CAA talent agent; and the crazed Slattery, who wants to work with Hamm again after their Mad Men days. Hot on their trail are two cartoonish mobsters (Joe Lo Truglio, Mather Zickel) desperate to recover a briefcase that was switched with Gail’s at LAX and contains information about their boss’ (Sabrina Impacciatore) plans to dismantle the global financial system. Their quest eventually brings them to Hamm, whose private security (Tobie Windham) enforces not with his fists or a taser, but with an obscure promise to make anyone who tests him “real sick.”
Gail’s travels are occasionally interrupted by Fourth Wall-breaking commentary from the film’s narrator, a mailman played by Fred Malmed. It’s one of the aspects of the movie that doesn’t work, but Gail Daughtry’s framework is less essential than the inspired jokes throughout. Wain and Marino riotously showcase the most banal aspects of LA, a signature of their delightfully dumb humor, which almost always lands as intended. Granted, some unfamiliar with their brand of comedy may take a while to get on its wavelength, and others may never understand why it’s funny. Still, there are enough non sequiturs and random punchlines blended with raunchy and occasionally dark-as-hell asides to keep the viewer off-kilter yet chuckling throughout.
There’s an irreverent surprise around every corner in Gail Daughtry, and Deutch fits right in with her comedian costars. Her impressive range renders the silliest moments without winking at the audience, but she also never reduces her character to a mere comic device. It’s also a joy to watch celebrities of Hamm and Aniston’s caliber poke fun at their image, even if the movie doesn’t challenge Being John Malkovich (1999) in its self-referentiality. Outside of last year’s disappointing The Naked Gun, few comedies today attempt to be pure joke machines. Wain and Marino deliver a movie that will probably take some time to be discovered and cherished for what it is, but after a few rewatches, much like the director’s other features, it’s sure to become a cult favorite.
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