Gail Daughtry and the Celebrity Sex Pass Is Beautifully Implausible

The shenanigans in David Wain’s new film will test your patience—mostly in a good way.

Thirty years ago, on a not very special episode of Friends (“The One With Frank Jr.,” for the record) Ross and Rachel swapped “Celebrity Freebie” lists: top fives of famous people with whom they would each choose—and be allowed by their partner—to have consequence-free sex. Ever the culture vulture, Ross opted for Isabella Rossellini, leading to the most incongruous Blue Velvet shout-out in prime-time history. Rachel, meanwhile, chose Chris O’Donnell, John F. Kennedy Jr, Daniel Day-Lewis, Sting, and, in a shocker, ex–Hardy Boy Parker Stevenson. The heart, it has been said, wants what it wants. 

David Wain’s new film, Gail Daughtry and the Celebrity Sex Pass, turns on an egregious no-strings-attached mishap, complete with a cameo from the erstwhile Ms. Green. The setting is Wilbur, Kansas, all picket fences and strip malls, where former high school sweethearts Gail (Zoey Deutch) and Tom (Michael Cassidy) are set to be wed. She’s bubbly and sweet, beloved by her neighbors and beauty parlor clients; he’s gormless and visibly out of his depth. Both are seemingly happy to go through the motions till death do them part. Pregaming an author event at their local bookstore, Gail and Tom start hypothesizing about their celebrity freebies; since the writer in town for the signing is Jennifer Aniston—there to hawk a no-frills cookbook of “Sensible Suppers”—they both agree that she’d be a suitable fantasy fling. 

Cut to Tom in flagrante delicto a few hours later in the back of the store with America’s Sweetheart. “We talked about this,” he pleads to Gail, who’s mortified, as is Jennifer, which doesn’t stop her from arranging to send Tom some DVDs of Friends (he only knows her from The Morning Show). Heartbroken, but determined to get even on her own set of ethical terms—and egged on by her standard-issue sassy best pal, Otto (Miles Guttierez-Riley)—Gail puts her game face on. Otto is off to Los Angeles for a hairdressing convention and suggests she tag along. Their target: Jon Hamm, a handsome prince ensconced at the Chateau Marmont.

No sooner have Gail and Otto landed at LAX than they’ve caught a cab ride with Richard Kind, obtained some star maps, and learned about the........

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