I wasn’t sure what to expect from a film called Gail Daughtry and the Celebrity Sex Pass. A Wizard of Oz parody wasn’t on my bingo sheet, however. It wasn’t until about halfway through the film that I picked up on the parallels. In retrospect, though, it was clear from the get-go. Not only is Gail Daughtry from Kansas, but her name is a play on Dorothy Gale. She also wears a blue dress and ruby shoes for much of the film. Those are subtle touches, although the rest of the film is as over-the-top as comedy gets. Whatever mindset the screenwriters were in, they were undoubtedly over the rainbow.
Instead of following a Yellow Brick Road to the Wizard, Gail (Zoey Deutch) follows Hollywood Boulevard to find Jon Hamm. Only then can she return home. Why? Because her fiancé Tom (Michael Cassidy) picked Jennifer Aniston as his celebrity sex pass. Wouldn’t you know it, Aniston was in town, and she was game. It’s the biggest disaster since Ross removed Isabella Rossellini from his celebrity freebie list. Gail believes that the only way she can reconcile with Tom is to have sex with her celebrity sex pass, Don Draper himself.
She arrives in Hollywood with fellow hairdresser Otto (Miles Gutierrez-Riley), although he’s not the only friend of Daughtry. While trying to hunt down Hamm, they encounter stand-ins for the Scarecrow, Tinman, and Cowardly Lion: an agent who wants to make his mother proud (Ben Wang), a washed-up photographer who wants the perfect shot (Ken Marino), and John Slattery, who wants to be relevant again after leaving Roger Sterling behind. At first, I thought Slattery would be a walk-on cameo, especially considering how many celebrities randomly pop up. Slattery sticks around for the rest of the movie, however. Like everyone else, he fully commits, no matter how ridiculous the material gets.
The film is unapologetically absurd, but is Gail Daughtry and the Celebrity Sex Pass funny? It’ll likely depend on how much you liked director David Wain’s past work. Wain is best known for Wet Hot American Summer, which audiences weren’t ready for in 2001. Wet Hot American Summer is now the definition of a cult classic, however. I can imagine Gail Daughtry having a similar slow burn to cult status. Gail Daughtry offers some of the biggest laughs you’ll have at the movies all year. That’s not to say every joke hit a bullseye. There aren’t any groaners, but a handful perhaps go on too long or lose focus. Half of the time, I forgot why exactly Gail needed to meet Hamm, despite the title literally spelling it out.
There’s also a subplot involving Sabrina Impacciatore as a Wicked Witch of the West and her henchmen, one of whom is played by Joe Lo Truglio. While they’re all fun to watch, it feels like the filmmakers wrote themselves into a corner with these characters, using an action climax as an easy out. For a film that borrows heavily from The Wizard of Oz’s structure, Gail Daughtry seems to make itself up as it goes along. It’s a comedy that throws everything it has at the audience. Not all of it sticks, but just enough does if you’re in the right mood. And what frame of mind would that be? About as high as a rainbow should do it.