Gail Daughtry and the Celebrity Sex Pass: We’re off to see Jon Hamm

We weren’t ready for David Wain in 2001, when his now-classic Wet Hot American Summer landed with a splat for both critics and audiences. A quarter of a century and five feature films later, Wain has carved out a niche in the realm of irreverent comedy with a cohort of stars—Paul Rudd, Amy Poehler, and Elizabeth Banks, to name a few—always down for his antics. In Gail Daughtry and the Celebrity Sex Pass, Wain brings his usual brand of humor to a whimsical parody on The Wizard of Oz. And while Wain may tend to overly rely on well-worn gags, his mix of regular collaborators with new blood in the cast make for a refreshing comedy.

Zoey Deutch (Nouvelle Vague, Juror #2) is the eponymous Gail Daughtry, a hairdresser in small-town Kansas who loves her town (per her local newspaper op-eds on “Why I’ll never leave”), her best friend Otto (Miles Gutierrez-Riley, Smile 2) and her fiancé Tom (Michael Cassidy, Army of the Dead). Tom and Gail are moving smoothly along the high-school-sweetheart-to-marriage-pipeline until Tom takes a hypothetical celebrity hall pass too far with a serendipitous chance to hook up with Jennifer Aniston (delightfully dry-witted in her brief cameo as herself, on tour for a cookbook). Gail, devastated and egged on by Otto, decides she has to even the score by tracking down and having sex with her own hall pass: Jon Hamm.

Luckily, Otto’s already heading to Los Angeles for a workshop from their favorite hairdresser, so Gail tags along to achieve her goal. After a mishap at the airport results in Gail accidentally trading briefcases with two henchmen delivering world-domination-worthy documents to the movie’s wicked witch Ludovica (Sabrina Impacciatore, her Italian hysterics from White Lotus seamlessly transferring to her role here as a mafiosa), Gail and Otto find themselves mired in her evil plot. 

It’s a goofy and slightly overwrought premise that’s brought charmingly to life by Wain and frequent cowriter Ken Marino (The Ten, Role Models, Wanderlust). Gail sets off down the yellow brick road of Hollywood Boulevard and collects her Scarecrow (Ben Wang as a beleaguered Creative Artists Agency assistant), Tin Man (Marino as a former paparazzo), and Cowardly Lion (John Slattery as John Slattery, out of work and practicing self-defense in a garage). Wain and Marino have fun both referencing their source material and goofing on Hollywood—an industry they paint as empty of magic now as Oz. 

Like any good comedy, Gail Daughtry has a strong script and a cast ready to go to bat for a laugh. Wain’s endless Easter eggs and sight gags are at work here as usual, starting off with an adult man on a tiny bike doing paper delivery around the neighborhood—a moment as stupid and small as Bill Hader doing the “check please” signing motion when asking a waiter for more wine in Wain’s They Came Together, and one that will certainly stick with me the same way. Throwaway lines and background bits are as funny as—and sometimes funnier than—the biggest punchlines. And while some bits fall flat, like an extended sequence in “Weird Al” Yankovic’s backyard, mile-a-minute jokes mean the batting average still ends up high. It helps that Wain found a muse in the form of Deutch, whose winsomeness sells both her character and the plot. She’s game for physical gags and goofs but never goes over-the-top in her delivery, instead matching the film’s off-kilter energy. The rest of the cast are equally excellent, with Wang as a standout with his casual, off-hand delivery of silly lines (“He did the deed, now you gotta do the do” as a response to Gail’s whole deal.) Hamm, too, plays himself with a disarming charm that complements Deutch’s earnestness. There are a couple drawbacks to this massive cast of characters and full-speed-ahead plot. Some skits overstay their welcome, like an extended sequence in “Weird Al” Yankovic’s backyard and a literal Western standoff with Ludovica. Gail’s character, too, ends up underdeveloped, making her arc of breaking away from her small town life land flat. 

Despite these flaws, you have to admire Gail Daughtry for going whole-hog on the antics. Wain’s comedy is inextricable from the people he’s surrounded himself with for over two decades, and the result are movies that feel like a group of friends getting together to do stupidly fun shit. And over those 20-plus years, his humor has neither stayed stuck in the past nor become glossed over with Hollywood polish, instead maintaining a sense of absurdism that aligns it with newcomers like John Early, Josh Sharp and Aaron Jackson, Andrew DeYoung, Molly Gordon and Nick Lieberman—perhaps proving we’ve finally acquired a taste for his brand of comedy.

If you enjoyed this article, please consider becoming a patron of Hyperreal Film Journal for as low as $3 a month!