Gail Daughtry and the Celebrity Sex Pass comes to us from the team of David Wain and Ken Marino. Director/co-writer/producer Wain came up as a journeyman comedy director, while co-star/co-writer/producer Marino is primarily known as a prolific character actor. (I might add that they are respectively the drummer and lead vocalist of the Middle-Aged Dad Jam Band.) Given the premise, the title, and the long list of connections that Wain and Marino have racked up over their long and respectable careers, it should come as little surprise that the movie comes with a hugely stacked cast of celebrities who showed up to make fun of themselves. So let’s get to it, shall we?

The eponymous Gail Daughtry (exec producer Zoey Deutch) hails from a sleepy rural town in Kansas, the only town she’s ever seen in her entire life. She’s the high school cheer captain who hooked up with the high school star quarterback (Tom, played by Michael Cassidy). They’ve been romantically linked for their entire lives, all the way through college, and now they’re two weeks away from getting married.

The plot kicks off shortly after Gail is introduced to the concept of a “celebrity sex pass”: a hypothetical scenario in which each partner of a monogamous couple decides which celebrity they’d get a free pass for extramarital sex with. Arbitrarily, Tom chooses Jennifer Aniston (playing herself), who just happens to be going through town on a tour to promote her new book. One thing leads to another and Gail literally catches her fiance up to his balls in Jennifer freaking Aniston.

Confused and heartbroken, Gail latches onto her coworker and token BIPOC gay best friend (Otto, played by Miles Gutierrez-Riley), and joins him on a convention in Los Angeles. The convention is further complicated when a baggage mixup puts her into direct conflict with an incompetent thug (Sergio, played by Joe Lo Truglio) hired by what could only be described as an Italian anarchist terrorist (Ludovica, played by Sabrina Impacciatore).

Meanwhile, Gail goes to see a psychic (played by Kerri Kenney-Silver) who looks into her crystal ball and deduces that Gail’s marital problems will all go away if she evens the score. Which means that Gail has to find, seduce, and fuck her childhood celebrity crush: Jon Hamm (also an exec producer, playing himself).

(Side note: The real Jon Hamm has been married to Anna Osceola since June 2023. She’s never even mentioned in the film.)

To help in her comically unlikely quest, Gail and Otto meet a comically unlikely assortment of LA locals.

• Ben Wang plays Caleb, a young delusional go-getter with dreams of being a big-shot talent agent.
• Marino plays Vincent, a paparazzo who considers Jon Hamm his white whale.
• John Slattery (another exec producer) plays himself as a washed-up has-been, especially bitter since Hamm hasn’t returned any of his calls since “Mad Men”.

(Side note: The real John Slattery has picked up a number of acting gigs since “Mad Men” wrapped. For instance, he reprised Howard Stark in Captain America: Civil War and Avengers: Endgame, he got a small yet crucial supporting role in last year’s Nuremberg, and he currently has a lead role in the ongoing TV show “The Rainmaker”. In 2022, Slattery and Hamm were both in the cast of Confess, Fletch — a film that admittedly, nobody saw.)

In case it wasn’t immediately obvious — and seriously, it should be at this point — the film gets increasingly blatant as a modern parody of The Wizard of Oz. If Dorothy wanted to have sex with the Wizard. To be sure, the movie leans heavily on getting comedic mileage out of references to the beloved children’s classic in the context of an R-rated comedy. I might add that using a universally known and beloved story as a template works surprisingly well as a cultural shorthand, keeping the plot tight and the runtime brief.

More importantly, while this is a comedy about a protagonist who wants to have sex, it really isn’t a sex comedy. There’s surprisingly little sex or nudity in this picture. In fact, most of the comedy stems from the basic conceit of The Wizard of Oz set against the backdrop of modern LA.

Dorothy and Gail are both naive, wide-eyed, pure-hearted Kansas girls on a quest through a strange land. The difference is that in Wizard, the contrast of the plain Kansas girl against the fantasyland setting helps to make Oz more magical and the quest more adventurous. In this picture, the contrast of the ignorant rural woman against the jaded and heightened Tinseltown makes for legitimately funny jokes about the stupidity of the characters and the nature of showbiz in general.

Which brings me to the overall themes at play. Remember, Dorothy and her friends went out to see the Wizard so they could ask for his help, only to find that he was a plain old humbug who couldn’t do anything except to confirm that nobody ever really needed his help all along. Without getting too deep into spoilers, that’s not exactly how things play out in this movie. Even so, the point stands that Gail and her friends set out to meet Jon Hamm the celebrity, only to meet Jon Hamm the mortal human. Those two are not the same thing. And that revelation says a great deal about the nature of celebrity worship and parasocial relationships in the modern world.

On the other hand, the movie flips the script in a pivotal way with regard to our protagonist. After all, Dorothy was a girl who wanted to escape her sepia-toned farm and go out to see the world, only to realize that everything she ever needed was in her own backyard the whole time. With Gail, it’s the opposite. Here we have a young woman who’s spent her entire life in small-town Kansas, who never knew or dreamed of anything bigger than her hometown, gradually coming to claim her own independence and spread her wings.

In the course of fucking a total stranger outside of wedlock. Sure, it sounds comical, but an unfaithful intercourse showed Gail just how ill-advised her engagement was and directly led her to broaden her horizons. That isn’t the first time such a thing has happened. (“Lady Chatterley’s Lover” comes to mind.)

In all honesty, I had a good time with Gail Daughtry and the Celebrity Sex Pass. While the Wizard of Oz references can get aggressively ham-fisted, it helps to develop the themes and comedy in a great many clever and surprising ways. And of course it was always a neat little surprise to see which celebrity cameos would pop up, even if some of them don’t make sense. (For instance, there’s one particular celebrity I could mention who quite famously resides in Las Vegas, not Los Angeles.)

Still, the jokes are funny, everyone came to play, and the runtime is quick enough that the film doesn’t overstay its welcome. You might want to wait for a home release on this one, but I can recommend checking it out.