“Gail Daughtry and the Celebrity Sex Pass” is absurdism done right

Jennifer Aniston has a problem that most aspiring actors would die to have: She’s too beloved. Factor in that she’s also too recognizable, too beautiful and apparently too eager to sign a million-year Aveeno skincare contract in blood, and you get a little thing I like to call “subversive ubiquity.” This is where an actor widely known for one long-running role, usually on television, finally concedes that disappearing into another character is all but impossible. But instead of accepting their Faustian fate and relegating themselves to being famous for fame’s sake, they attempt to subvert their cultural ubiquity into something just as interesting, something that is, in its own way, an art form: playing themselves.

Now, one might think that it would be easy for an actor to play themselves. There must be no prep involved, so they can just show up to the set and fire off some lines, right? Wrong. Playing oneself is more difficult than it seems. It’s a skill that requires both an innate understanding of your own identity and the world’s perception of you. Do you think Aveeno could tie with Dove and Jergens in a 2024 survey of America’s most trusted body lotions if Jennifer Aniston couldn’t convince people that her home office is a Wayfair showroom that is also, somehow, a kitchen? I think not. Aniston’s great skill isn’t acting; it’s knowing how to be both the everywoman and herself. It’s why she largely sinks in dramas but succeeds in comedies, where she can portray a version of herself that makes people laugh just by thinking, “Isn’t it so funny that Jennifer Aniston said that?”

That is just one reason why I’m delighted to tell you that “Gail Daughtry and the Celebrity Sex Pass” is far and away the year’s funniest movie — I might even be so bold as to say it’s within the top five comedies of the decade so far. Directed by “Wet Hot American Summer” creator David Wain and co-written by Wain and Ken Marino, “Gail Daughtry and the Celebrity Sex Pass” is just as head-spinning as its 40-character title. Take a deep breath at the film’s start, because you won’t have a moment to retain your composure once Wain and Marino’s blissfully imaginative, “Wizard of Oz”-riffing odyssey of a screenplay gets going.

A brilliant cameo from Aniston promoting her new cookbook, with such adventurous epicurean dishes as “boiled hot dogs and peas,” serves as the film’s inciting event. When plucky, small-town bride-to-be Gail Daughtry (Zoey Deutch) and her deadbeat fiancé Tom (Michael Cassidy) attend Aniston’s book signing, they agree that Aniston could be Tom’s fantasy celebrity sex pass. There’s no way Tom would ever actually get the opportunity to have sex with Aniston, anyway. That is, until Tom forgets his jacket inside the bookstore. Suddenly, Gail finds herself looking to even the playing field and sets off on a journey to Tinseltown alongside her best friend, Otto (Miles Gutierrez-Riley), in search of the sensual, hairy-chested comforts of one Jon Hamm.

After laughing until I cried at Aniston’s bit part, where she plays an airhead version of herself that only an actor well-versed in the principles of subversive ubiquity could be, I assumed there was no way the film could maintain its high. Most comedies plummet halfway through their second act, when the jokes get stale, and studios demand some kind of emotional stakes. But “Gail Daughtry and the Celebrity Sex Pass” stays soaring, swooping through high-concept absurdist bits, running gags that don’t lose their repeat value, and a slew of cameos that zig just when you think they’ll zag. Move over, “Wicked”; there’s a new Dorothy in town, and her name is Gail Daughtry!

Let’s get something important out of the way: Don’t bother with watching the trailer before you seek out “Gail Daughtry and the Celebrity Sex Pass” for yourself. Trailers may be integral to a film’s promotional process. But no editor in the world could recut something like “Gail Daughtry” into a two-minute preview that accurately conveys just how joyous and stupid this film is. Relying on a trailer would be a disservice to your soul, not to mention that watching it would spoil a couple of key comedic bits and cameos that are best seen within their intended context. (I recognize the irony in revealing Aniston’s, which isn’t in the trailer. But since it arrives at the start of the film, and because there are no less than five terrific sight gags and perfectly timed punchlines within her portion of the movie, there are still plenty of surprises waiting to be enjoyed.)

“Gail Daughtry and the Celebrity Sex Pass” is not a comedy in the contemporary sense of the word. Wain didn’t design this film to fit into clip-farmed compilations on TikTok or even one-minute clips on YouTube. Its closest resemblance is to Wain’s 2014 romantic comedy parody, “They Came Together,” which, despite having no shortage of memorable one-liners, functions best as a whole. The ideal way to settle into the tone and rhythm of “Gail Daughtry” is by plunking down in the dark of a movie theater or your living room, preferably with a friend or two, and giving the movie your undivided attention. There hasn’t been a film with so many legitimate blink-and-you’ll-miss-it gags in some time. Consider when Gail and Otto arrive in Hollywood and hop in a cab driven by Richard Kind. Instead of spending the money on a pricey establishing shot of the car driving on the 101, Wain inserts a brief vintage clip of a ’70s-era taxi, humming along the road. It’s the making of a perfect joke: totally superfluous and uniquely dumb.

Want more from culture than just the latest trend? The Swell highlights art made to last.Sign up here

Yet, Wain and Marino cleverly use seemingly unnecessary visual asides like this to create a quasi-love letter to Hollywood filmmaking, asserting that there is no shortage of the kinds of tales you can tell about a fish out of water — and how you can tell them. Their take on “The Wizard of Oz” is remarkably fresh, with Deutch playing the perfect Dorothy, fresh from Kansas and looking to bang a celebrity. She has both Judy Garland’s bubbly conviction and wide-eyed naivete, along with the kind of comedic timing that few actors exhibit today. Her delivery is assured yet self-effacing, no doubt the result of having parents in the industry (actress Lea Thompson and director Howard Deutch). Say what you will about nepo babies, but there can be a strangely ironic lack of vanity to those who are born within the golden gates and aren’t trying to forge a career on self-obsession alone.

That’s also why it’s so thrilling to see Deutch in a role like this, and Wain and Marino leafing through their decades of experience trying to get comedies made in Hollywood as the industry steadily shifts toward dramas. With its jokes about the inner workings of Hollywood agents at CAA and the trappings of fame and fortune, “Gail Daughtry” could easily feel like inside baseball. Instead, the movie welcomes audiences of all kinds by playing up LA’s inherent absurdity. The film’s version of this city is as cutthroat and ridiculous as it is in real life, which makes it all the more compelling and enjoyable to see gullible Gail navigate her way through every outrageous situation. Maybe coming to Hollywood to try to find and have sex with Jon Hamm isn’t any more of a fool’s errand than moving to Tinseltown with three bucks and a suitcase full of dreams of seeing yourself on the big screen.

As she walks Hollywood Boulevard, Gail adds new members to her crew, just as Dorothy does as she skips down the yellow brick road. Alongside Otto, there’s Caleb (Ben Wang), an aspiring agent whose cocksureness gets him fired from his dream job; Vincent (Marino), a former paparazzo whose failure to capture his white whale celebrity still haunts him to this day; and John Slattery (the real one), who’s fallen on hard times ever since “Mad Men” went off the air.

(Sony Pictures Classics) Jon Hamm as himself in “Gail Daughtry and the Celebrity Sex Pass”

Here’s another running bit that would be so easy to muck up or exploit. The big joke of “Gail Daughtry” could be that Slattery joins the gang to help locate his old costar, with whom he’s lost touch after being left on read too many times. But Marino and Wain wisely temper this punchline throughout their script. They’ve crafted the ideal framework for Gail’s journey, where calling on Slattery is never unwelcome. Time and again, I found myself relishing the fact that what I was watching didn’t play like a feature-length bit from an old Emmys telecast, the kind that already wears out its welcome with the audience by the time the presenter gets to “and the nominees are.”

The film’s brilliance comes from Wain and Marino knowing how to pummel the viewer with jokes while measuring each punchline’s individual weight. Drop too many heavy-hitters at once, and the viewer will be dizzy in seconds, watching cartoon ruby slippers dance in a circle around their head. But balance the scales, and the audience will build and refine their comedic muscles, able to withstand anything that’s thrown at them. And that’s an important skill.

Few modern comedies know how to build within their narrative; it’s why something like “Stop! That! Train!” loses steam, or even the “Naked Gun” reboot can’t maintain its rhythm all the way to the end credits. A rise-and-fall tempo is necessary —  even if, in the case of “Gail Daughtry,” the undulation is almost imperceptible. Its closest cousin in formula is “The Invite” (what a great pair for a double feature), which maintains its comedic stride but has a very different goal from Wain’s film. Here, as trite as it sounds, laughter is medicine. The setup is the shot, and the punchline is the chaser, and they both go down smooth.

I haven’t even had a chance to tell you about the ingenious side plots, like Gail and Otto’s desire to attend a hairdressing convention with their favorite style guru, Remy Fontaine (Thomas Lennon). Or the antagonist, the Wicked Witch of West Hollywood, Ludovica (“The White Lotus” breakout Sabrina Impacciatore), who is hell-bent on taking down the world’s financial systems for hysterical personal reasons. And, of course, the team does eventually meet up with Hamm, too. But those threads are waiting to be unspooled on your own trip to Hollywood via the silver screen. In remixing one of cinema’s most revered classics with singular comedic flair, Wain has made a contender for his best film that succeeds by tributing his own loony industry. There may be no place like home, but there’s no place like Hollywood, either.