A young woman visits Los Angeles with the express purpose of having sex with Jon Hamm in David Wain’s very funny but a tad slight comedy, Gail Daughtry and the Celebrity Sex Pass.
Gail Daughtry and the Celebrity Sex Pass is a David Wain picture. You may not know Wain by name, but there’s a good chance you’ve seen his work. From TV work on MTV’s The State sketch comedy show and episodes of your favorite funny shows to films like Wet Hot American Summer (one of my top three comedies), They Came Together (one of my wife’s), or Role Models (and more), Wain (and co-writer Ken Marino) has made a career of comedies that are straightup funny for being funny but also work on the satirical and absurd level, working in and around tropes of storytelling and genre conventions. Thus, Gail Daughtry is a very funny film about a woman trying to bang Jon Hamm while also serving as a satire of Hollywood and its reputation among outsiders.
So why does Gail Daughtry, a cheery girl from Kansas played by Zoey Deutch, go on a quest in Los Angeles to bed the star of Mad Men? To even the score with her fiancé. Having just introduced the idea of the celebrity sex hall pass, well, he bangs Jennifer Aniston (making the most of her cameo, as does everyone else in a film filled with other cameos). To make it all good, Gail and her best friend and fellow hairdresser, Miles Guiterrez-Riley’s Otto, head to Hollywood. Gathering a group; wanna be agent Ben Wang of American Born Chinese, down his luck paparazzi co-writer Ken Marino, and John Slattery playing himself with a wonderful over-the-top desperation, they work their way closer and closer to the star of the criminally unseen Confess, Fletch; all while in the sights of the evil Sabrina Impacciatore, trying ot claim a mixed-up briefcase via henchmen, mainly Joe Lo Truglio.
It’s all good fun, with a big smile and a lot of spirit. Wain and Marino, who head up Middle Age Dad Jam Band – check them on YouTube, excel at satires of a specific style. Not as directed and pointed as say Airplane, but upping regular antics to absurdity. Wet Hot American Summer, They Came Together, and so much of The State (gotta love a sketch comedy show taking the piss out of that other famous sketch comedy show) set the example. Thus, Gail Daughtry and the Celebrity Sex Pass becomes a Hollywood personal journey satire and one of filmmaking itself. It’s purposely shiny and saccharine but inherently raunchy (it is about trying to get busy with the notable 30 Rock side character), and Wain and the gang can find that balance with a sincere earnestness.
It is very funny, constantly earning laughs. But part of it doesn’t fully work; the energy is a little off. Almost like it’s pieced together over time as they needed, rather than a full production, abandoning a sense of cinematography and design for what can be shoved in cleanly today while everyone’s available. Wain works best when expanding the satire to a slight absurdist level of how people act within films, how plots come together, and just being absurd for the sake of it. That’s how Gail does best, a series of gag sequences slowly making the way forward. These include an overly and purposely out of character Weird Al, an omniscient narrator used in fun ways, and showing the hand that “this is a film,” it gets into bits around the central premise of how Hollywood is often taken in movies. The premise is light, the characters state their needs and depths with a purposeful exposition, and everyone moves forward. This allows Wain and Marino to build up to oddity. With this matter, it feels a little loose. Wet Hot is also a series of vignettes as well, but it commits to the bit more. But even with a lightness, Gail Daughtery is very funny and will earn those laughs and get a “oh that was cute! Such a good time” but not a cult following like WHAS or Wain’s other works. As it goes, it becomes clearer that it is riffing on one very specific movie. One my wife caught on before I did, but we verbally identified at the same time, making a new game in “catch how elements are used.” About the time we stated it, it became more and more obvious. Yet, it’s a fun element, often told directly in other reviews – boo.
As a cast, all are game. I’ve always enjoyed Zoey Deutch, and she gets the aw-shucks innocence. Damn, does she look like her mom, Lea Thompson. She’s a wonderful anchor to everything around her, playing well with Marino, Slattery, Wang, and Guiterrez-Riley. Nice to see most of the State pop in. Of course, Truglio (you know him as Boyle on Brooklyn 99 if you don’t recognize the name) and Marino are all over. But Michael Ian Black, Kerry Kenney, Kevin Allison, and Tom Lennon come and go. No Robert Ben Garant, Michael Patrick Jann, and Michael Showalter. Although funny that Dropout’s Zac Oyama appears here and in Showalters’ disatrously awful Christmas Film Oh What Fun of last December. 
Gail Daughtry and the Celebrity Sex Pass, directed by David Wain and starring a radiant Zoey Deutch, is a fun romp. While it doesn’t quite reach Wain’s absurd heights of Wet Hot American Summer or They Came Together, it offers more than enough solid laughs and entertainment as the story unfolds. Nothing wrong in just lounging back and soaking up a nice comedy, one with game players and unexpected turns to the odd. And that’s what Gail Daughtry does. So… who’s your pass?