Directing: B-
Acting: B+
Writing: B
Cinematography: B
Editing: B-

When a movie knowingly leans into how dumb it is, it’s always a tricky prospect, a truly fine line between genuinely entertaining and outright embarrassing. Gail Daughtry and the Celebrity Sex Pass walks that line, with humor that lands maybe half the time. It does find its footing, at the very least, and eventually I was laughing pretty regularly in spite of how embarrassed I was for everyone involved.

There’s a sort of built-in defense of a movie like this “But that’s the point!” Well, the point only means something if it actually works, and unfortunately the first act works less than the rest of the movie does, which makes it easy to see audiences checking out early. I’m not sure it would even mean much if I assured you it’s worth the wait, especially since even I found it barely worth the wait, but there remains the fact that I did.

Honestly, either you’re going to be up for a deeply silly movie like Gail Daughtry or you’re not. The tone is set immediately, when only minutes after Gail (Zoey Deutch) and her husband Tom Soursap McNoodleman (get it??—played by Michael Cassidy) agree on who their celebrity sex passes are, Tom has sex with Jennifer Aniston in the back room of a stop on her cook book tour in Kansas City. And therein lies the premise telegraphed by the movie’s title: the only way to even the score is for Gail to travel to Los Angeles with her bisexual hairdresser colleague and friend, Otto (Miles Gutierrez-Riley) and have sex with her celebrity sex pass, John Hamm.

I will credit Gail Daughtry with this, my favorite thing about it: this is a movie with real affection for all of its incredibly dumb characters. In someone else’s hands, this movie would find ways to poke fun at Kansas City as much as it does Los Angeles and the people who live there, and it really does neither; not one of these characters is ever individually the butt of the joke. These are all people who are naive and yet somehow things keep working out for them, right down to a couple of Midwesterners who consistently meet Angelinos who are happy to help Gail in her quest to bed John Hamm. The more this aspect of the movie becomes clear, the more enjoyable it becomes.

Said Angelinos, by the way, include John Slattery, here depicted as a washed up actor who hasn’t had any work since he costarred with Hamm in Mad Men—which ended in 2015. He’s actually been in lots of stuff since then, but that’s not the point. Slattery is actually one of the principals in this film, but Jennifer Aniston is the first of countless, major cameos that might make one wonder how the hell whoever directed this managed to get them all on board. Well, Gail Daughtry and the Celebrity Sex Pass is directed and cowritten by David Wain, who happened to direct and co-write the 2001 film Wet Hot American Summer. And that film featured the much younger Paul Rudd, Elizabeth Banks, and Michael Ian Black; he later directed the 2012 film Wanderlust, which featured both Rudd and Aniston. Guess who all appear briefly in Gail Daughtry? And this just scratches the surface of the wall-to-wall cameos here. This guy clearly has some pull, and tons of people are perfectly happy to appear in his new movie, even if maybe they don’t know whether it’s great or just . . . kind of fine.

Wain eventually draws an unsubtle parallel with The Wizard of Oz, slotting Hamm into the role of the Wizard—sort of. Gail is a kind of Dorothy (oh, did I mention Gail is from Kansas City?), and she assembles a ragtag group of friends, which includes Caleb (Ben Wang), the overly ambitious guy from Creative Arts Agency; Vincent the papparazzo (Ken Marino) who’s “white whale” happens to be a candid shot of John Hamm; and of course, John Slattery. This movie, of course, needs some knowingly contrived villains, which include Italian actress Sabrina Impacciatore as Ludovica, who is awaiting delivery of a suitcase full of all the paperwork plans for taking down the global financial system; and her two henchmen, played by Niccolo (Mather Zickel) and Sergio (Joe Lo Truglio, also a David Wain mainstay who was in all the aforementioned of his films).

While we get ridiculously pointless voiceover narration by Frank the Mailman (Fred Melamed), the evil Ludovica’s briefcase of paperwork is the subject of a mixup that serves as the plot’s deliberately flimsy excuse for finally getting Gail and John Hamm in the same room together. How does that happen, you might wonder? Aside from knowing it veers between comic sex and comic violence as a bit of spice sprinkled on all the cheese, you’ll have to watch the movie! Just go in with fairly low expectations, fully expect it to marinate in its own cornball sensibilities, and you’ll have a pleasant enough time. I did, and eventually found myself cackling in an otherwise empty movie theater. I just had to get to the point where I could surrender myself to what this movie was doing, and then it kind of worked out.

*Midwestern hairdressers on a mission in Los Angeles just can’t help but to have fun with it all.*

Overall: B