As a general rule of thumb, when someone goes out of their way to tell me how funny and smart they are….they’re usually not.

Gail Daughtry and the Celebrity Sex Pass is that kind of person as it mounts up to being an occasionally amusing but mostly insufferable attempt at a comedic romp that breaks the fourth wall and insists upon itself as being charming and goofy when it’s just self-indulgent and ridiculous.

Small town hairdresser Gail Daughtry is engaged to her devoted high school sweetheart, Tom. Her life takes a turn when a trip to a book signing leads to Tom meeting – and sleeping – with his “celebrity pass”. Reeling from the betrayal, Gail impulsively joins her friend Otto on a trip to Los Angeles, where a psychic convinces Gail that the only way to save her marriage is to “even the scales” with her own celebrity pass: Jon Hamm. Thus begins an epic journey through Tinseltown as Gail and Otto join forces with a talent agency assistant, a paparazzo, and actor John Slattery, all in the search for Hamm. Along the way, they collide with celebrities and are hunted by a group of Italian assassins as they get ever closer to finding the elusive star.

I’ll be the first to admit that when it comes to director David Wain and his frequent collaborator and co-screenwriter Ken Marino that I am VERY hit and miss.  This very obviously lands in the latter category as it tries to shoe horn a sickly faux sense of charm as it takes pot shots at both the small town experience and it’s flip side in navigating the streets of Hollywood.

Wain and Marino essentially start the film like it’s a greyhound in the racing blocks waiting for the starters pistol and the plastic rabbit at the end of the rail that’s just out of reach.  Rather than trying to get us invested in characters or even their situation, this film leans entirely too hard on the gimmicky premise that it’s built on.  It sets up the tired couples joke about ‘celebrities you can sleep with’ and wastes no time taking it all from 0 to about 100mph in about a 5 minute span.  There’s almost no character set-up, the reveals and the moments never feel earned, it’s all a race to get Gail to LA and we never actually care that her fiancé just banged Jennifer Aniston in the back of a book store because he was stupid enough to think that he could.

Once Gail and her prototypical gay best friend make it to LA, then run through a myriad of big city vs small town jokes while throwing in the occasional crude innuendo along the way and once the “chase elements” of the film that come into play and allow the film to move we feel like we’re stuck somewhere in-between a mildly offensive 80’s sex comedy and a movie industry satire that can’t stop making tired jokes about Hollywood as a whole.

Shockingly there’s actually some really talented people in this movie, but they’re just going along with the shtick and the mediocre jokes as the likes of Thomas Lennon, Jo Lo Truglio, Sabrina Impacciatore, John Slattery (who for some reason is the butt of half the jokes in the movie) & Ben Wang don’t really get to do much in support of Zoey Deutsch as our heroine.  Combine that with a total of about 9 cameos (that we caught) and only one joke that actually worked, this was all very much an unfunny slog filled with people marvelling at their own wit….which was never there in the first place.  Even Jon Hamm as the end goal of the story felt like he was playing a muted version of himself from the Skip The Dishes adverts.

This was just a mess, Gail Daughtry and the Celebrity Sex Pass wants us to think it’s the funniest thing since sliced bread, without giving it any actual heart or emotional stakes for the characters.  It’s hard to enjoy the adventures of a set of characters that you honestly don’t give a damn about.