So here’s the set-up for Gail Daughtry and the Celebrity Sex Pass. Gail (Zoey Deutch) is a hairdresser in smalltown Kansas who’s been having a conversation with fiancé Tom (Michael Cassidy) about which celebrity each of them would like to have as their celebrity sex partner – a free pass, all just a fun fantasy. Tom has gone for Tilda Swinton. Gail, at Tom’s prompting, has gone for Jon Hamm.
All harmless nonsense until the pair of them go to a book signing by Jennifer Aniston, who’s promoting a cookbook full of joyless recipes. Tom decides Aniston might also be a worthy Sex Pass partner and instantly promotes her, dumping Tilda in the process. Gail thinks nothing of it – all fun etc – until, after the signing, she discovers Tom and Jen going at it hell for leather on a sofa.
Which is why Gail decides that she will after all attend that hairdresser convention in LA, with her “bi-everything” hairdresser buddy Otto (Miles Gutierrez-Riley). And so, leaving Kansas for the first time in her life, the two of them head towards the city where hairdressing royalty will convene and, who knows, Jon Hamm might help her even the score.
A girl from Kansas heading towards a glittering city with a sidekick whose name is an anagram of Toto – suspicions (fuelled by the IMDb trivia section bluntly saying so) that this is a reworking of The Wizard of Oz are confirmed by later developments, as Gail and Otto pick up a trio of deadbeat travelling companions. Caleb (Ben Wang) is a nobody at a big talent agency. Vincent (Ken Marino) is a paparazzo who’s been trying since forever to get a money shot of Jon Hamm (him again). And John Slattery is John Slattery the actor, still smarting about Hamm’s success since Mad Men, since when he’s barely worked.
Which is the Tin Man, which the Lion, which the Straw Man? I thought I had worked it out, but then there was a scene where Otto – who’s obviously Toto, right? – saves the day because he has a metal plate in his head. So he’s the Tin Man now?
There’s no doubt about the Wicked Witch – Sabrina Impacciatore as Ludovica, a crime boss with a plan to undermine the global financial system.
Add in a gratuitous Henry Winkler cameo, Elizabeth Banks blurring by, a brief moment from Weird Al Yankovic and Penn Jillette, plus Elizabeth Perkins (of Big fame) as a cab driver, not forgetting the sight of Jennifer Aniston’s legs pointing heavenward as she is pleasured by Tom, plus that Wizard of Oz arc – spiritual improvement for everybody – and that global financial undermining plot, the whole hairdressing convention strand, plus Jon Hamm to get in (eventually) and you cannot accuse this film of wanting to be elegant.
You cannot accuse this film of not trying either. Or of not knowing a few people. Was that Paul Rudd towards the end?
The effect is of being bulldozed into submission. Slattery is funny, charming and disarming (someone needs to be). Hamm, when he turns up – he’s the Wizard, obvs – plays up to his media image of being overweeningly self-obsessed. Deutch is cute as an asexual Dorothy figure. They’re all good really.
But the law of diminishing returns sets in. Early laughs at knob jokes, or the cheery mailman narrator (Fred Melamed) dropping the F bomb, give way to a fixed-grin, which yields ultimately to a “what now?” as the latest bit of byzantine plotting is revealed.
I liked all the cameos – Aniston funny, Winkler funny, Yankovic also funny – but the celebrity flypasts reveal a lack of faith in the leads, leaving Deutch and Gutierrez-Riley spinning in their wake. Individual moments good, overall vibe a bit meh. You may want to give it a pass.
Gail Daughtry and the Celebrity Sex Pass – Watch it/buy it at Amazon
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© Steve Morrissey 2026
