Writer-director David Wain has been making comedy films and TV for almost three decades now. Not all of what he’s made is for everyone, but the choice stuff is both funny and different. With Wain’s latest film, Gail Daughtry and the Celebrity Sex Pass, the premise and humour are right there in the title. That’s efficient, sure, but it’s also too easy in this case.
Zoey Deutch gamely plays Gail as a cross between wide-eyed ingenue and down-home sweetheart. After granting her fiancé a so-called “sex pass” with a celebrity of his choice, a chance encounter with Jennifer Aniston inadvertently blows up Gail’s entire life and worldview. In no time, she’s off to Los Angeles from Kansas (cue an obvious Wizard of Oz joke, which the film delivers) with her gay best friend Otto (Miles Gutierrez-Riley) on a quest to bed Jon Hamm. Complications arise via a cadre of Wain mainstays (from The State, Children’s Hospital, etc.) and an angry Sabrina Impacciatore, but these elements all feel more dutiful than inspired. While it’s fun to see John Slattery arrive on the scene, playing a version of himself, and co-writer Ken Marino once again adds a funny spin to the proceedings, the actors involved aren’t really stretching their comedic talents much. On top of that, the film’s local feel doesn’t help either; Wain seems to have shaped his bit-based narrative on which L.A. locations were most convenient to shoot in. Weird Al making a cameo with an assault rifle at his house may have popped as a joke in 2005, but now it just seems tired.
In 2026, meanwhile, it may be vaguely possible to chortle at some of the gags in Gail Daughtry and the Celebrity Sex Pass, but it’s just as easy to shrug at them. Wow, Hollywood is a vacuous place? Movie cliches are silly when you examine them in detail? Small-town bumpkins are clueless? Fine, I’m not above it. But I am over it.
