What If ‘The Wizard of Oz’ Involved Having Sex With Jon Hamm?

Every hero’s journey starts with a single step, they say. For Gail Daughtry (Zoey Deutch) — ace hairdresser, proud Midwesterner, and enthusiastic bride-to-be — it begins with a flight to Los Angeles. Normally, Daughtry would be back in her idyllic hometown of Willowbrook, Kansas, putting the final touches on her upcoming wedding to her longtime sweetheart, Tom (Michael Cassidy). Instead, she’s accompanying her co-worker and best friend, Otto (Mile Gutierrez-Riley), to a convention in the City of Angels, partially out of revenge and partially to save her relationship. The stakes are truly life or death here.

Because Gail and Tom had the conversation that most couples have at one point or another, about the “celebrity sex pass.” You know the drill: there’s one famous person that you get to boink without your significant other getting upset. Think of it as a sort of get-out-of-cheating-jail-free card. Most of us know this is a hypothetical situation, because when are you ever going to get the chance to be in the same room with a movie star, a supermodel, a Super Bowl MVP?

Except Tom … well, let’s just say the two of them went to a book signing, and his brand new celebrity crush was there — you should discover the A-lister in this equation yourself — and things went a little too far. So now Gail has gone to Hollywood, USA, on a mission. Once she sleeps with her celebrity crush, then the score is evened, romantic equilibrium will return to normal, and the two can live happily ever after. The lady must walk down righteous paths, face seemingly insurmountable obstacles, slay the modern-day equivalent of dragons. Nothing can stop Gail from seeking her Holy Grail. Our hero must fulfill her quest to [checks notes] fuck Jon Hamm.

In other words, Gail Daughtry and the Celebrity Sex Pass is exactly like The Wizard of Oz, complete with a plucky young woman from the Sunflower State. Only instead of a yellow brick road, we get Sunset Boulevard. And in lieu of a scarecrow, a tin man, and a cowardly lion, we get a CAA agent-in-training (Ben Wang), a paparazzi (Ken Marino, the film’s cowriter), and John Slattery (John Slattery). And while there’s no Wicked Witch of the West, there is a female Mafia crime lord (The White Lotus‘s Sabrina Impacciatore) who’s looking to retrieve her contraband. And also, rather than “there’s no place like home,” the takeaway is much closer to “there’s no place like a bungalow at the Chateau Marmont, where you may experience untold carnal bliss at the hands of the guy who played Don Draper in the seventh greatest TV show of all time.” (That’s according to our list, by the way, which gets a direct shout-out in the movie. A thousand thank you’s.)

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If this sounds to you like the basis for a great sketch, or at least one sturdy enough to nearly sustain itself as a feature-length comedy, you are not alone. Gail Daughtry is directed by David Wain and co-written by Wain and Marino, two of the founders of the Nineties sketch collective known as The State. That group lived fast, died young, and left behind two seasons of an MTV show that gets a bigger fan base every year and gets better the more you rewatch it. Fond memories of porcupine racetracks and $240 worth of pudding, as well as a genuine cult classic in Wet Hot American Summer (2001), have ensured its legacy among comedy nerds in the know, and given that seven of the 11 members of the group show up here, this essentially qualifies as a State film. It definitely shares the same blissfully ridiculous sensibility as their best short-form work, the kind that allows for an Our Town-style narrator, a scene involving a door slamming on someone’s foot that goes on for close to two minutes, and a sort of anything-goes notion of free-form silliness. An alternate title could have been Wet Hamm American Summer.
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His Hammness does show up, tongue planted firmly in his photogenic cheek, and reminds you that nobody does handsome-guy self-mockery better than Jon Hamm. John Slattery is, not surprisingly, a close second — the Mad Men pairing is both a meta-joke, a nostalgia trigger, and a chance for them to pitch future buddy-comedy pairings. Other celebrities drop by, naturally, and the Hell-Ay showbiz digs fly fast and furious and occasionally stick.
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The key to making all of this work is really Deutch, who knows how to lace an all-American sweetness with a sense of anarchy lurking right below the surface. You’re rooting for this plucky, small-town everywoman to salvage her dignity, repair her relationship, and restore order to the universe so that she and her guy can ride off into the Willowbrook sunset. Mostly, though, she makes you want Gail Daughtry to succeed in nailing her celebrity sex pass. Because every real hero deserves a happy ending in more ways than one, and the chance to click their heels and cry, There’s no place like Hamm. There’s no place like Hamm. There’s no place …