A wildly entertaining reinterpretation of *The Wizard of Oz* by director David Wain, *Gail Daughtry and the Celebrity Sex Pass* is a mosaic of zany ideas. Some don't quite land, but most do—provided you catch the tone of the humor. Written by Wain and his frequent collaborator Ken Marino, the comedy features an incredible cast of hilarious people who, at times, play absurd versions of themselves. Jon Hamm, Jennifer Aniston, John Slattery, and Elizabeth Banks, among others, make cameos alongside a cast of lesser-known but equally talented actors.
The film stars Zoey Deutch, who—in addition to boasting an impressive body of work—has proven her knack for this kind of absurdist humor (see 2019’s *Zombieland: Double Tap*). Wain directs a series of episodic segments following characters as they travel along a yellow brick road made of surreal gags and Hollywood-skewering jokes. It is all rather wacky and ridiculous, but it made me laugh out loud.
Director: David Wain
Writers: Ken Marino, David Wain
Stars: Zoey Deutch, Jon Hamm, Kerri Kenney
For those of us who loved the MTV sketch show *The State* (1993–1995) or Wain’s film parodies like *Wet Hot American Summer* (2001) and *They Came Together* (2014), *Gail Daughtry* will feel as comforting as a warm blanket. *The State* was a breeding ground for comedic talent; many of its members went on to create and appear in dozens of other shows (*Viva Variety*, *Reno 911!*, *Childrens Hospital*, etc.), while Michael Showalter has become a highly respected director, with credits including the indie comedy *The Big Sick* (2017) and the upcoming adaptation of Colleen Hoover’s book *Verity*.
Whenever Wain and Marino reunite with various members of *The State* (Michael Ian Black, Thomas Lennon, Kerri Kenney-Silver, Joe Lo Truglio, among others), something special usually emerges. Although the material doesn't always gel as a cohesive whole—take *The Ten* (2007), an anthology film parodying the Ten Commandments—the result always delivers big laughs. Deutch plays the naive small-town Kansas girl who gives the film its title: a hairdresser planning to marry her fiancé and lifelong love—the wittily named Tom Soursap McNoodleman (Michael Cassidy)—in two weeks. She is a young woman who is both naive and intense; neither she nor Tom has ever been with anyone else.
However, after sharing their respective "celebrity free-pass" lists, Tom almost immediately runs into his chosen star and seizes the opportunity. Outraged—since she hadn't thought they were serious about actually acting on the plan—Gail decides to track down her own pick, Jon Hamm, and sleep with him to even the score. Thus, Gail sets off to see the "Wonderful Wizard of Hollywood," accompanied by her coworker Otto (Miles Gutierrez-Riley)—whose name is an anagram of Toto. As the story unfolds, Gail Daughtry’s journey parodies the structure of Dorothy’s adventure in Oz, with the difference that Gail’s destination is the mecca of cinema.
Just as New York was "another character" in *They Came Together*, Los Angeles becomes one here. But instead of capturing the city's true essence, Gail and Otto are drawn to Universal Studios' CityWalk and—following their hotel concierge's recommendations—to local hotspots like McDonald’s, Starbucks, and 7-Eleven. Gail and Otto begin their search for Hamm, picking up friends along the way. These include Vincent (Marino), a former paparazzo dreaming of photographing Hamm; Caleb (Ben Wang), an aspiring talent agent at CAA; and the eccentric Slattery, who wants to work with Hamm again after their time together on *Mad Men*.
Hot on their heels are two cartoonish mobsters (Joe Lo Truglio, Mather Zickel), desperate to retrieve a briefcase—accidentally swapped with Gail’s at LAX—that contains information on their boss’s (Sabrina Impacciatore) plans to dismantle the global financial system. Their search eventually leads them to Hamm, whose private security guard (Tobie Windham) maintains order not with punches or a Taser, but through a vague threat to make anyone who dares to challenge him "very sick."
Gail’s journey is occasionally interrupted by fourth-wall-breaking commentary from the film’s narrator: a mailman played by Fred Malmed. It is one aspect of the movie that doesn't quite click, yet the Gail Daughtry narrative framework is less essential than the inspired gags that pepper the film. Wain and Marino gleefully showcase the most banal aspects of Los Angeles—a hallmark of their delightfully absurd humor—almost always achieving the desired effect.
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