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If It Only Had the Nerve

The ‘celebrity sex pass’ is a decently fun concept to base a comedy around. A lot of couples have one -the one celebrity crush they are theoretically permitted by their partner to have sex with should the chance arrive. It is of course something highly unlikely to happen; but the notion of it happening, and for the other then to seek out their own celebrity sex pass to even the score is a funny premise. It’s not too far off a general sitcom episode formula. But what kind of mind would pair that with a pastiche of The Wizard of Oz?
David Wain apparently, whose new movie Gail Daughtry and the Celebrity Sex Pass does just that. It took a little while admittedly for me to pick up on the particular piece that Wain was structuring his story around, but it does become incredibly unsubtle after a time. It’s an approach worth admiring for its uniqueness, and how much fun Wain and his collaborators are clearly having with the idea, which lends itself well to the hyperbolic pseudo-parody style of Wain’s comedy seen in the likes of Wet Hot American Summer, They Came Together, and even his last movie A Futile and Stupid Gesture. But while this course for the movie is periodically entertaining, it often goes so hard for the silliness -and with mixed results as to its various comedy bits- that it comes short in substance.
Zoey Deutch plays Gail, a hairdresser in Kansas who, shortly before her wedding to fiancé Tom (Michael Cassidy) discusses the idea of a celebrity sex pass as a purely hypothetical joke. But then Tom winds up at a book signing with Jennifer Aniston and one thing leads to another when Gail bursts in on them. A furious Gail leaves for a convention in Los Angeles with her friend Otto (Miles Gutierrez-Riley) and is brought to the conclusion that in order to save their marriage she has to have sex with her celebrity pass: Jon Hamm. So Gail and Otto journey around Los Angeles in an effort to find Hamm, building a ragtag crew along the way including aspiring celebrity agent Caleb (Ben Wang), washed-up paparazzo Vincent (Ken Marino), and Hamm’s struggling former Mad Men co-star John Slattery.
I’ll say this that for a movie about celebrities from Wain, who has in-roads with a lot of Hollywood, the celebrity appearances are fairly reigned in. Hamm and Aniston are probably the biggest names that play themselves and Hamm has been in self-satire mode for more than a decade. Otherwise, beyond a couple minuscule cameos from Wain’s Wet Hot American Summer gang, the notables here are the likes of Henry Winkler and Weird Al Yankovic -in his most delightfully unhinged movie performance in a while. Slattery gets by far the biggest treatment of these and earns it -the typical case of an actor known for quite serious parts delighting in cutting loose with wildly silly material.
He is the film's stand-in for the Cowardly Lion, next to Caleb's Scarecrow and Vincent's Tin Man. Gail Daughtry is of course a play on Dorothy Gale -in several scenes she is wearing something blue with red shoes, while Otto with his inconspicuous bone earrings is her little Toto and the role of the Wicked Witch is filled out with Sabrina Impacciatore as an Italian crime boss pursuing Gail and her friends after a sensitive briefcase gets switched with hers at the airport. There are also analogues for Flying Monkeys, the Yellow Brick Road, the Emerald City and the Wizard himself. It is amusing to pick up on these parallels early on, while they are slick and discreet, though eventually Wain abandons subtlety and starts quoting The Wizard of Oz directly in both dialogue and visuals. And while it is a fun conceit, the bit quickly becomes a distraction when it is clearly being employed as a barely-concealed reference rather than a joke -especially towards the end of the last act where the winking touches become rather obnoxious.
This is true also of some of the jokes. The film’s sense of humour is a very mixed bag -as has honestly been the case with Wain’s work overall. Some of the gags and especially the little details they are comprised of can be really smart and funny in unexpected ways. Even just aspects of the general atmosphere, which is very whimsical and innocent for a movie where the end goal is sex. The movie leans into its heightened reality and lack of rules -both in the tone of the world and the rather simple characters. And while there is some charm and an attractive looseness that comes out of this, it also makes for some rather dull and awkward comedy.
There are several routines built through the movie that are structurally and rhetorically old-hat, and they hit their punchlines exactly as expected, minus any spontaneity. There are comic depictions of places and institutions that feel antiquated -such as both Vincent’s former “journalism” world and a standing old west movie set. There are comedy beats that don’t particularly make sense or are just weak, such as Gail’s choice for her and her companions to strip to their underwear to get past a security gate and then use their clothes as a weapon. And there are plenty of jokes that just land with a thud, like Vincent’s complicated old paparazzo nickname that the script tries multiple times as though aware that it is bombing with the audience. Even some bits that are honestly funny come within a context or framework that is mediocre.
The type of absurdism that Wain is channeling is in the vein of something like Monty Python or Kids in the Hall, but he and his collaborators are not Monty Python or Kids in the Hall. A very particular threshold is required and neither the script nor the performers meet it, apart from -strangely enough- Slattery and Hamm (also Fred Melamed as the mailman narrator). Deutch ought to be perfect, given her established talent for wry sarcasm, but the winking insincerity doesn't suit her and can get annoying. Impacciatore is out of place as well as a frenzied stereotype, and Marino overextends himself severely, with a grasping, mugging quality to his performance that only emphasizes the weak material. 
Gail Daughtry and the Celebrity Sex Pass had ambition and a fun concept that it once in a while does live up to. The originality of the Wizard of Oz motif in spite of its strangeness is worth some credit too. But its script and energy fall quite short of the spontaneity it suggests and there are also several missed opportunities that can't be made up for by slamming a door into a guy's foot repeatedly for over a minute straight. That is what the movie feels like in its shakiest moments, and unfortunately there are a lot more of those than the alternative.

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