Aside from the likes of Adam McKay, Judd Apatow, and Seth Rogen and his collaborators, it’s hard to think of a filmmaker who has been more influential to comedy this millennium than David Wain. While his films have never reached the same level of box office success as those contemporaries, Wet Hot American Summer has become enormously influential, packed with an absurd wealth of comedic talent and a hyper-specific style of humor that felt genuinely ahead of its time in 2001. Hell, it still feels ahead of the curve today. All of which is to say: Wain’s filmography has largely been a hit for me. I even think 2014’s They Came Together is an all-time comedy classic.
Gail Daughtry and the Celebrity Sex Pass finds Wain tackling one of his zaniest premises yet. The film follows Gail Daughtry (Zoey Deutch), a woman happily engaged and counting down the days until her wedding to her fiancé, Tom (Michael Cassidy). Their idyllic romance comes crashing down when Tom cashes in his celebrity sex pass to hook up with Jennifer Aniston. Heartbroken and desperate for a distraction, Gail heads to Los Angeles with her good friend Otto (Miles Gutierrez-Riley), where she encounters a psychic who tells her the only way to set things right is to cash in her own celebrity sex pass – Jon Hamm.
Through Gail’s journey across Los Angeles and Hollywood, Wain has a blast playing with celebrity cameos, skewering genre conventions, and, above all else, crafting a supremely stupid comedy with stretched-out gags in a way that only he can. In short, the film is delightfully nonsensical in the same vein as the rest of his filmography. Every joke is either as dumb as humanly possible, or hilariously depraved, nuanced, subversive, or so hyper-specific that only about 10% of the audience will fully appreciate it. The film ping-pongs between those two comedic modes with ease, making for an endlessly entertaining romp.
Another major selling point is the supporting cast, something that has always been a hallmark of Wain’s comedies. John Slattery, Ken Marino, and Ben Wang are all terrific as the band of misfits accompanying Gail on her quest to seal the deal with Jon Hamm. Slattery, in particular, is a riot, playing a washed-up version of himself who can’t find work and is still waiting on a text back from Jon Hamm after Mad Men ended in 2015. Joe Lo Truglio and Sabrina Impacciatore are equally memorable as the film’s antagonists, gleefully chewing the scenery every chance they get. I’d also be remiss not to shout out the always-incredible Fred Melamed, who doubles as Gail’s mailman and the film’s wonderful narrator.
Beneath all the absurdity, Wain essentially crafts a warped version of The Wizard of Oz, with Jon Hamm serving as the Wizard at the end of the road; the mythical figure who can grant everyone their deepest desires. It’s a hysterical premise, and Wain squeezes every ounce of comedic potential from it. Zoey Deutch, who has repeatedly proven herself to be a phenomenal comedic performer, carries the film with effortless charm, fitting perfectly into Wain’s absurdist sensibilities. And once Gail finally reaches Hamm, the payoff is tremendous. I won’t spoil the specifics, but their chemistry is off the charts, and Hamm’s willingness to poke fun at himself makes the entire finale sing.
It’s admittedly difficult to review a David Wain film because the filmmaking itself is intentionally unflashy. His direction exists primarily to give his performers the room to deliver the dumbest jokes imaginable, and that’s exactly what makes his work so distinctive. My only real criticism is that, compared to some of his best films, this one has a slightly lower laugh rate. It throws a joke at the audience every 30 seconds or so, and there are a handful that don’t quite land. Even so, Wain fires off so many gags, callbacks, and absurd lines of dialogue at such a relentless pace that it’s hard to dwell on the misses before another joke comes flying your way.
The only real knock against the film is that it doesn’t quite reach bona fide comedy-classic status for me in the way Wet Hot American Summer and They Came Together did. Even so, it’s still an incredibly funny movie, packed with outrageous gags, inspired celebrity cameos, and a fully committed ensemble that keeps the entire thing afloat. Far from Wain’s best work, but another wildly enjoyable and worthwhile addition to one of comedy’s most singular filmographies.



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