The Wizard of Hamm

The celebrity “hall pass” is a fun little game many couples play. (Or so I’ve been told.)

The scenario is simple: Each partner gets to name one celebrity who, were they ever to have the chance, they could have sex with, and the other partner would be totally okay with it. It’s complete fantasy, of course, but that hasn’t stopped people from making their choices over the years.

This concept of a “hall pass” has inspired multiple storylines in pop culture. For example, you probably remember the season-three episode of Friends (“The One with Frank Jr.”) where Ross and Rachel create lists of five celebrities they’re allowed to sleep with if they ever have the chance. Ross’s list, which he laminates, includes Isabella Rossellini, but Chandler convinces him she’s “too international” and suggests replacing her with Winona Ryder because she’s “more local.” And then, at the end of the episode, Rossellini herself walks into Central Perk, but she dismisses Ross because she’s not actually on the list.

Good stuff.

All these years later, it’s Rachel herself — or Jennifer Aniston, anyway — who kicks off the plot of the very funny new movie Gail Daughtry and the Celebrity Sex Pass when she has sex with Tom (Michael Cassidy). Just minutes earlier, he told his fiancée, Gail (Zoey Deutch), that Aniston was his celebrity sex pick. Actually, it was Tilda Swinton, but he changed his mind after meeting Aniston at a book signing right there in their rural Kansas town and being instantly smitten. Believing that Gail permitted Tom to have sex with her, Aniston makes Tom’s fantasy come true.

Gail can’t believe it actually happened. Hurt, she decides to join her friend Otto (Miles Gutierrez-Riley, Off-Campus) on a trip to Los Angeles, where she begins to track down her own freebie, Jon Hamm, so she can even the score. Along the way, Gail and Otto join forces with a talent agency assistant, a paparazzo, and actor John Slattery, all in the search for the Mad Men star.

Yes, it’s a gloriously, unapologetically silly premise, and thankfully, the movie never wastes a second pretending otherwise. Instead, it leans into the absurdity with complete confidence, turning the whole thing into one extended, escalating joke that keeps finding new ways to surprise you.

To be clear: The surprise isn’t that the movie is funny. It’s how relentlessly funny it is. The comedy — both in joke quantity and tone — is pitched at about an 11, which is exactly where it belongs, with jokes flying by so quickly that if one doesn’t land, another is already halfway to the plate. And that’s including all the jokes and references that are hidden in the background on billboards and other signage, too. 

The cast includes Ken Marino and David Wain (who co-wrote the film), Joe Lo Truglio, Thomas Lennon, Richard Kind, Michael Ian Black, Kerri Kenney-Silver, and Sabrina Impacciatore, plus Henry Winkler, Elizabeth Banks, “Weird Al” Yankovic, Penn Jillette, and Paul Rudd, with some folks popping in for glorified cameos, others hanging around longer, and all of them looking like they’re having a blast. 

Yes, Hamm himself is in the movie, too.

There’s a wonderful anything-goes energy to the whole enterprise that makes the film feel like Wain (who also directed) and Marino had an idea, called up a bunch of their buddies from The State, Reno 911, Wet Hot American Summer, and other projects, and they just made it happen. Almost every new scene introduces another funny face, which contributes to the movie’s loose, “everyone came to play” atmosphere. 

Wain and Marino’s shared comedic sensibility is all over Gail Daughtry — between the rapid-fire jokes, absurd premise treated with complete sincerity, and an ensemble cast of funny people bouncing off one another. 

That said, one of the movie’s most enjoyable aspects is that the whole thing is basically a playful riff on The Wizard of Oz. It’s not an adaptation by any stretch, but a contemporary comic take that sprinkles in clever references and mirrors the classic story in unexpected ways. Gail’s journey throws her together with an increasingly eccentric collection of characters, and half the fun is spotting the nods while the movie cheerfully blazes its own trail. 

At the center of it all is Deutch (Everybody Wants Some!!), who is, as always, effortlessly adorable. She has that rare ability to ground even the most outrageous situations with sheer likability. But the movie belongs to Slattery, Hamm’s Mad Men buddy, here playing a less successful version of himself. Slattery walks away with scene after scene thanks to his impeccable comic timing. Special mention also goes to Fred Melamed (A Serious Man), whose mail man/narrator sets the scene and keeps things moving with just the right amount of dry wit.

What’s most appealing about the film, though, isn’t any individual performance or even any particular joke. It’s the feeling of being in on one giant, gleefully ridiculous gag. The movie isn’t trying to be sophisticated. It’s trying to make you laugh consistently for a little over 90 minutes, and more often than not, it succeeds.

Could Gail Daughtry have gone straight to streaming? Absolutely. So many comedies do these days.

But that would have been a shame.

Because while you could wait a few months and watch this movie on your couch, you’d be cheating yourself out of its biggest asset: the audience. Comedies are one of the few genres that genuinely improve when you’re surrounded by strangers laughing at the same punchlines. Every laugh builds on the next until the entire room is in on the joke together. This film needs an audience.

Gail Daughtry and the Celebrity Sex Pass is a silly movie. It knows it’s a silly movie and doesn’t try to be anything other than that. And that’s exactly why it’s such a good time.

I’m giving it a B+.