Gail Daughtry and the Celebrity Sex Pass Is Beautifully Implausible

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 best spots in town
to get a burger (McDonald’s), a coffee (Starbucks), and a blow job (Foot
Locker). They also accidentally obtain the briefcase of a reigning Mafia queen
bee (Sabrina
Impacciatore) who has designs on bringing down the global financial system and
is willing to kill the strangers who’ve made off with her documents. Other
impediments to Gail’s righteous carte blanche booty call include
misfiring hitmen, unctuous personal assistants, and a machine-gun-toting
“Weird” Al Yankovic, who helpfully tells her and her friends to “eat it” while
chasing them off his property.
David Wain does not make realistic, or even halfway plausible, movies. This laxity is
his badge of honor,  and he wears it
well.
Suffice
it to say that Wain, who once cast Aniston opposite Paul Rudd in 2012’s Wanderlust,
does not make realistic, or even halfway plausible, movies. This laxity is
his badge of honor, and he wears it
well. Where a status-climber like Judd Apatow cultivates a strenuous, and
largely disingenuous, naturalism—John Cassavetes by way of SNL—Wain has
no use for respectability. He’s yet to abandon the slovenly, see-what-sticks
shtick of Wet Hot American Summer (2001), an epochal work that
has informed a swath of postmillennial alt-comedy. By sticking to his guns—and
also letting them misfire, or shoot blanks—Wain runs the risk of seeming like
an inept veteran, when he’s actually an old master of his very particular chosen
form. 

Gail
Daughtry and the Celebrity Sex Pass is not a good-looking movie: Kevin Atkinson’s cinematography
is so hypnotically bland that Main Street USA and the Inland Empire become
virtually indistinguishable from one another. The performances are broad to the
point of active mugging; the storyline doesn’t so much strain continuity and
credibility as leave them to bleed out in a ditch. This is all to the good.
Wain and his co-writer, Ken Marino, who appears as a veteran paparazzo helping
Gail navigate the City of Angels, have each worked on plenty of “normal”
television and streaming series since their days on MTV’s The State. They’ve
had successful careers meeting the industry halfway—especially Marino, who’s
usually the funniest part of whatever he’s in. What they refuse to do is make
compromises on their own time. Instead, they play a game of (rubber) chicken
with themselves and the audience, torquing artificiality and contrivance into
its own screwily lucid sort of worldview: a wryly complacent gaze into the
pop-cultural abyss. 

Wain
is often called a satirist or a parodist, which is true for instance of the
winking, ruthless Nora Ephron–esque They Came Together (2014), which
leaves vintage rom-com tropes to ripen and rot on the New York City pavement.
The label doesn’t always fit, however. “I don’t consider Wet Hot
American Summer a spoof at all,” Wain told The Film Stage; “it’s
just a movie really sourced in actually going to summer camp, and it’s funny.”
The skeleton key to unlocking the director’s sensibility—not that it’s
necessarily airtight in the first place—might just be Wet Hot’s gee-whiz,
summer-stock metaphysics—the wholesome, theatre-kid excitement of getting your
friends together and putting on a show. Think of the wonderfully sincere sequence
where a group of preteens perform “Day by Day” from Godspell, an
almost enchanted interlude that feels plucked from memory. And then there’s the
final act of Wain’s deceptively conventional and Apatow-adjacent 2008
masterpiece Role Models (co-written with Marino), in which the
protagonists are finally reconciled by a rousing game of Medieval cosplay—an
immersion in nerd
culture enacted with a welcome lack of condescension toward characters and
audience. 

It
makes sense that such an inveterately playful filmmaker would finally get
around to riffing on The Wizard of Oz: Victor Fleming’s 1939 classic is
the primal scene of Hollywood escapism, after all. The sheer slack-jawed
obviousness of the references here is part of the point: “Gail Daughtry”
inverts “Dorothy Gale” as surely as “Otto” scrambles “Toto,” and Hamm eventually
refers to himself as a wizardly “man behind the curtain.” Within the film’s
Emerald City framework, John Slattery, playing a B-list celebrity, serves as a
modern version of the Cowardly Lion (“Put ’em up, put ’em up,” he mumbles,
shadowboxing in his garage). Ben Wang, playing a Creative Arts Agency rookie,
is a scatter-brained Scarecrow manqué, and Marino as the cynical, heartless
photographer has shades of the Tin Man. Slattery’s performance is wonderfully
unhinged; he’s funniest when he’s being used as a punching bag, whether
rhetorically—as in an uproarious series of text messages narrating his
incremental estrangement from Hamm (who’s left his buddy on read for several
years)—or literally, as when he gets a hotel room door slammed on his ankle 34
times, each jolt punctuated by its own piercing yelp of “Ow!”
There is a fine
line between liberated and lazy, and Gail Daughtry refuses to pick a
lane on principle.
David
Lynch used to suggest that most of his movies were spiritual remakes of The
Wizard of Oz, and Wain’s embrace of low-rent
surrealism can feel Lynchian at times; by following a guileless ingenue
through a freaky version of “Hollyweird,” Gail Daughtry becomes the
director’s Mulholland Drive, right down to the script’s winking anxiety
about the perils of show-business-as-usual. There aren’t a lot of comedy
directors who are so willing to deal in outright alienation effects, like the
repetition-compulsion of Slattery’s battle with the door, or the gratuitously
brutal violence of a late action sequence seemingly staged in one of the same
locations as Quentin Tarantino’s Once Upon a Time in Hollywood. 

And then
there’s the narrator, played by the honey-voiced character actor Fred Melamed,
who starts out cheerful and folksy about Gail and her friends but begins
wearying of the WTF nature of the material around the same time we do.
Melamed’s descent into raging dyspepsia is a signal that Wain knows very well
he’s wasting his—and our—time and trusts that we don’t mind. There is a fine
line between liberated and lazy, and Gail Daughtry refuses to pick a
lane on principle. The swerving is the point; the pleasure resides in the high-minded notion—rooted in the golden rule of
improv—that all jokes, including and especially the bad ones, are created
equal. 

It’s
hard to reconcile deliberately half-hearted humor with real emotion, and Gail
Daughtry and the Celebrity Sex Pass is deliberately underwhelming both as a
love story and as an attack on the culture industry. Wain loves his offhand
anticlimaxes; no surprises for guessing that, choosing between a cheating dork
on the one hand and Don Draper on the other, our heroine finally chooses
herself. But Gail’s parting words sum up the movie, its makers, and their
passions so nicely that they bear repeating. “Let’s keep it loose and freaky,”
Deutch tells Hamm before they float off together in a hot air balloon,
somewhere over the rainbow. ...