‘Gail Daughtry and the Celebrity Sex Pass’: A Delightfully Demented ‘Wizard of Oz’ Riff

As comedies fade from view in the cinematic landscape, we sometimes forget that certain directors have a vision and voice as firm as any acclaimed auteur. Just as you would know Martin Scorsese movie from a Christopher Nolan feature, you would know Mel Brooks compared to Judd Apatow. Comic voice matters, and there’s no one quite like David Wain, who has left his mark with cult classics like Wet Hot American Summer and They Came Together and even a more mainstream comedy like Role Models. With his latest feature, Gail Daughtry and the Celebrity Sex Pass, Wain and his former The State compatriots like Ken Marino (who also co-wrote the film), Kerri Kenney, Michael Ian Black, Thomas Lennon, and Joe Lo Truglio join up with some spirited actors for a strange, singular romp through Hollywood that will have you roaring with laughter (provided you’re on Wain’s wavelength).

Gail Daughtry (Zoey Deutch) works at a salon in a small Kansas town and is about to marry her high school sweetheart Tom (Michael Cassidy). When she brings up that her celebrity sex pass is Jon Hamm, her fiancé says he would choose Jennifer Aniston, who the couple has just met at a book signing. Tom then promptly sleeps with Aniston, which sends Gail and her best friend Otto (Miles Guiterrez-Riley) out to Hollywood so she can sleep with Hamm, even the score, and restore the relationship before the wedding. Along the way, they join up with a cast of kooky characters including rookie agent Caleb (Ben Wang), veteran paparazzo Vincent (Marino), and Jon Hamm’s Mad Men co-star John Slattery (John Slattery). However, their journey through Hollywood is threatened by an evil power broker (Sabrina Impacciatore) whose plans to tank the world economy are in a case that gets mixed up with Gail’s. 

It’s a little tough to describe why Wain’s comedies work so well since I wouldn’t say they’re for everybody. Role Models is an R-rated crowd-pleaser, and Wanderlust is an easy pitch, but what do you say about Wet Hot American Summer or They Came Together? They’re certainly parody-adjacent, but not quite the same as Brooks or a Zucker-Abrahams-Zucker comedy like Airplane! Yes, it’s funny that everyone in Wet Hot is way too old to be a teenage camp counselor and They Came Together is playing off Nora Ephron rom-coms, but Wain likes to take his work in a darker, stranger direction than simply throwing everything at the wall. These are not movies that have been focus-tested for maximum laughs. He knows what he wants and hopes the audience will come along.

For me, at least, I was more than happy to go on the ride. It was wise of Wain and Marino to use The Wizard of Oz as a story template, since it not only provides a good structure, but also provides plenty of room to take some shots at the way Hollywood usually gets depicted and lets the director offer his own Fractured Mirror feature. It’s no surprise that Deutch is delightful comic talent who has no problem anchoring the film, and she easily holds her own in the movie’s weirdest moments. But I was also impressed with Wang and Guiterrez-Riley, and Slattery kind of steals the movie playing a loser version of himself. When you throw in small roles from State cohorts, it all makes for a delightful, delirious spin.

Not everyone will get on board (such is the nature of comedy), but it’s certainly a film for those who love scenes like the one in They Came Together where Paul Rudd’s character and the bartender go on an extended back-and-forth with just the prompts, “Tell me about it,” and “You can say that again.” There’s one line said by Jon Hamm’s bodyguard Terrence (Tobie Windham) that I’ve been thinking about for weeks, and the only person I can share it with is a friend who saw the film at Sundance. It’s that kind of movie that clicks with you and isn’t meant to be a box office sensation, but those who love it won’t soon forget it.

I worry for the film’s fate as we’re in a far different place than when Wet Hot American Summer or They Came Together hit theaters. How does a cult comedy even happen these days? How does any comedy happen? The trailermakes the movie look far more mainstream than it is, and while that will likely mean poor CinemaScore (a metric determining audience expectation versus what they saw), not every great comedy has to reach the widest viewership. Gail Daughtry is a breath of fresh air, not only as a comedy in a marketplace where laughs are now either part of action blockbusters or awards contenders, but as a reminder that Wain, when given room, can make movies as distinct as any celebrated director. It would be a shame not to catch it as early as you can.

Gail Daughtry and the Celebrity Sex Pass opens in theaters on Friday, July 10^th.

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