When David Wain directs a comedy, you know what you’re getting: An overarching air of absurdity, unflinching commitment to the bit, cameos from just about everyone who was a cast member on Wain’s old MTV show The State, and gags that hit or miss. All of that happens in Gail Daughtry and the Celebrity Sex Pass, Wain’s latest comedy (co-written with Ken Marino) that takes a well-worn plot—a couple has an agreement that each is allowed to have sex with a certain celebrity—and takes off from there. That’s attached to a fish-out-of-water plot that casts a Midwestern rube in Hollywood, and at some point we realize it’s all a riff on The Wizard of Oz.
That rube is Gail Daughtry (a game Zoey Deutch), a hairdresser from Kansas who’s preparing to marry her even dimmer fiancé (Michael Cassidy.) After her husband surprisingly beds his own sex pass recipient, Gail heads to Los Angeles with her gay fellow hairdresser (Miles Gutierrez-Riley, the Toto of the piece) to pursue her own sex pass, Jon Hamm.
Meanwhile, they’re sidetracked by a crime plot involving a pair of switched suitcases and a female mobster (White Lotus veteran Sabrina Impacciatore) seeking to do her own Panama Papers and release documents containing all the world’s financial secrets. The crime subplot, for the most part, is filler, resembling a warmed-over version of Get Shorty.
But when the gags hit, they hit well, and Deutch expertly handles the role’s physical demands. Hamm, once he shows up, is wonderful, and it’s great to see him reunited with his old Mad Men co-star John Slattery, also playing a skewed version of himself. There are plenty of gags that don’t hit. Too much of the film is dedicated to surprise cameos, whether by Wain’s old pals from The State or other celebrities; the movie keeps stopping so guest stars can show up and riff. I guess it’s funny for “Weird Al” Yankovic to ironically tote a gun, but that was already a movie. Penn Jillette showing up looking unrecognizable just happened a few months ago in Marty Supreme. And since the sex pass happened on an episode of Friends, with Isabella Rosellini, Jennifer Aniston is naturally part of the proceedings.
This is David Wain’s first film as director since A Futile and Stupid Gesture, the 2018 movie about National Lampoon that wasn’t as good as the documentary. Wain’s best film is 2008’s Role Models, but the rest are uneven. Wet Hot American Summer is getting a 25th-anniversary re-release this summer and is much-loved, but I never got the appeal. Gail Daughtry and the Celebrity Sex Pass, like most of his work, is uneven, but the highs are better than those of most of his previous films.