Gail Daughtry and the Celebrity Sex Pass, 2026.
Directed by David Wain.
Starring Zoey Deutch, Jon Hamm, John Slattery, Ben Wang, Richard Kind, Ken Marino, Thomas Lennon, Sabrina Impacciatore, Michael Cassidy, Joe Lo Truglio, Fred Melamed, Michael Ian Black, Mather Zickel, Miles Gutierrez-Riley, Richard Ellis, Tobie Windham, Leon Masuda, Jennifer Aniston, Henry Winkler, ‘Weird Al’ Yankovic, Elizabeth Banks, Paul Rudd, Elizabeth Perkins, Penn Jillette, and Kerri Kenney.
SYNOPSIS:
When her fiancé uses their “celebrity pass” agreement, Midwest bride Gail Daughtry travels to Hollywood seeking revenge by pursuing her own celebrity encounter.
It shouldn’t be foolish or unreasonable to presume or have some hope that a movie titled Gail Daughtry and the Celebrity Sex Pass would have something insightful to say about how the titular arrangement (in which each participant of a relationship is allowed to have sex with one celebrity of their choosing should an unlikely but theoretically possible situation ever arise) and love at large through its comedy. One would imagine that’s the point in co-writer/director David Wain’s making this film (crafting the screenplay alongside regular collaborator Ken Marino, who also has a supporting role here). Alas, that is not the case.
This is an absurdist comedy, which isn’t necessarily surprising considering David Wain’s filmography. However, a movie about one character chasing down a celebrity crush to get even with her fiancé over catching him sexually intimate with his celebrity pass (they agreed to this moments before, although she didn’t think he was serious) leaning too far into organized crime shenanigans that increasingly become less grounded and more ridiculous culminating in a third act that simply loses one completely is a questionable creative choice.
What makes this more frustrating is that for the first 45 minutes or so, the filmmakers find that appropriate balance between a lustful quest that might save a relationship and a collision course with bumbling Italian goons trying to reclaim a briefcase of sensitive incriminating documents (accidentally swapped at an airport with our protagonist’s case of hairstyling kits en route to a seminar in Los Angeles where she also realizes her sex pass choice likely lives in the area), who are admittedly quite funny when the film isn’t trying too hard to elicit a laugh and resembles something along the lines of believable stupidity mining jokes from the usual mobster cliches (there is a great bit early on where a surveillance system finds a social media account with a picture making it clear specifically what location they are at, only for these dimwits to require a pot of coffee and to look a bit harder).
Presented as a story told by small town neighborhood mailman Frank (Fred Melamed) breaking the fourth wall, sometimes amusingly in front of bypassing civilians coming off as crazy, we receive a brief look at the long-standing relationship between Gail Daughtry (Zoey Deutch, who generally excels when a film calls her to get eccentric and weird, here often hampered by scattershot material) and high school sweetheart Tom (Michael Cassidy), the small talk made about the celebrity sex pass, and his impromptu sexual escapade with Jennifer Aniston in town promoting a cookbook. Naturally, Gail needs some time to think about the marriage, so she heads on a business trip, listening to her accompanying co-worker/friend Otto (Miles Gutierrez-Riley), who says they should also use the opportunity to go on a quest for her to bone her celebrity crush, Jon Hamm.
As everyone knows, the City of Angels is also filled with stars. The previously mentioned Italian goons (a consistently funny Joe Lo Truglio and Mather Zickel) become familiar with this firsthand, losing the valuables they’re supposed to deliver to their crime boss (Sabrina Impacciatore) while obsessing over having Gail take photos of them with a hurried but friendly Henry Winkler. That sets up the pursuit to get the briefcase back by any means necessary, whereas Gail and Otto regularly come into misinformation about the whereabouts of Jon Hamm, while also meeting colorful characters such as an intern with aspirations of being a celebrity manager (Ben Wang), a wearied and clueless but helpful paparazzi (Ken Marino) hunting his photography white whale (I’m sure you can guess who it is), or the Mad Men star’s former screen partner John Slattery, apparently living in a garage taking up martial arts due to not being in demand for roles.
The group also encounters other recognizable faces, though they are sometimes playing characters in the movie, which throws off the Hollywood aspect; Richard Kind plays a taxi driver. There is certainly fun to be found in the search for Jon Hamm (John Slattery even pretends they consistently talk after Mad Men ended while looking down at a one-sided text chain, something that is both funny and sad), but David Wain either doesn’t know what to do with this premise or is content doing something else that isn’t interesting or engaging at all.
It’s almost fitting that there is a childhood photo of Gail and Tom dressed up as characters from The Wizard of Oz, since watching Gail Daughtry and the Celebrity Sex Pass is comparable, except that instead of being off to see a wizard, they are looking for a celebrity for sex. Without characterization or purpose behind the story, even that layup concept is disappointing, especially once the movie fully transitions into watching these characters take on the mob. It also ceases to be funny by entirely embracing that aspect, working better when deriving laughs from satirizing its Hollywood setting and celebrity culture. Whether or not Gail and Jon end up having sex is something that won’t be spoiled here, but even that resolution is lacking. David Wain is the one who should be asking for a pass, and perhaps doing a redo on this mostly limp material to capitalize on its squandered potential.
Flickering Myth Rating – Film: ★ ★ / Movie: ★ ★ ★
Robert Kojder
