Movies these days have ample heavy material to deal with: conflicts are everywhere, chaos reigns under Trump, culture wars divide friends over issues happening half a world away, environmental catastrophes shape our way of life, and human flow complicates all matters above as a global migration crisis leaves countless people in limbo. Amid all these dire realities, Gail Daughtry and the Celebrity Sex Pass asks one of life’s life toughest and most significant questions: If you could sleep with any celebrity guilt-free, who would it be? In 2026, that question proves especially thorny depending upon which episode of Heated Rivalry is next in the queue. For Gail Daughtry (Zoey Deutch), however, the sweetest pie hails from TV’s Mad Men era.
Gail finds herself on a mission to find Jon Hamm after she poses the question of the celebrity sex pass to her fiancé (Michael Cassidy). Unlikely events necessity Gail cashing in her sex pass to even the score, so the plucky hairdresser from the Midwest races off to Hollywood to bang Don Draper. Gail’s quest ignites a madcap adventure as she touches down in Hollywood and realizes that she isn’t in Kansas anymore.
With her sex-positive BFF Otto (Miles Gutierrez-Riley) by her side, Gail makes her way down the Yellow Brick Road (i.e.: Hollywood’s Walk of Fame) and picks up a Tin Man and Cowardly Lion to round out her motley crew. One of them just happens to be John Slattery, who gamely accepts the prospect of reuniting the team from Stirling Cooper Draper Pryce.
The celebrity sex pass offers a fun game to play after the credits roll. Ask the film’s director/co-writer David Wain ( Wet Hot American Summer ) who his ultimate pass would be and the answer surprises. He cites late New York Mayor Ed Koch, the amiable quick-witted lefty and Greenwich Village icon. “I feel like he’s a guy that has a lot of energy and knows how to have a good time even though he’s no longer with us,” explains a deadpan Wain, speaking with That Shelf via Zoom.
Gail Daughtry and the Celebrity Sex Pass delivers good silly fun in its purest form. It encourages audiences to let loose and embrace the stupid. But while it enjoys a side of broad comedy that audiences see too rarely these days— Stop! That! Train! and Scary Movie aside—the film also plays into the allure of celebrity as Gail reflects audiences’ romantic fantasies of Hollywood stars.
“I feel like so often you hear about these weird stories about a celebrity and then you find out they are true,” says Wain. The director, clearly tired at the end a long press day, seems surprisingly short for words. But movies sometimes need no explanation. Wain invites so many Hollywood stars to get in on the joke—cameos range include Jennifer Aniston, Weird Al Yankovic, and Paul Rudd as themselves to nobodies standing in for the likes of Helena Bonham Carter.
As Gail and company navigate their maps to the stars, Wain says that working in Hollywood can reveal certain truth about celebrity. “People who are really famous are a bit insecure just because that’s part of what drives them and it’s true, but maybe of actors in general,” says Wain. “When you become really famous, it can’t help but affect you. If you’re really well known, like Jennifer Aniston, and you have to change your comings and goings, that can be somewhat exhausting.” It’s a point of comedy in the film that Hamm has become so elusive that even Slattery can’t access his former co-star without muscling his way through an entourage.
Wain says that the secret sauce for Gail Daughtry came together in the casting. A-level talent mixes with ingénues like Deutch—famous enough to carry a film, but fresh enough to disappear alongside stars playing themselves—and recognizable novelties like White Lotus breakout Sabrina Impacciatore as a mobster after Gail following an airport switcheroo with some suitcases. Call her the Wicked Witch of the West Coast.
“We try to mix up having more known people, less known people, and people who are more in the comedy world or part my own family of people that I’ve worked with over and over again,” explains Wain. His cast of regular collaborators includes Hamm, along with co-writer and actor Ken Marino, who plays one of the misfit toys that Gail collects along the way. (In this case a paparazzi photographer.)
“I have a shorthand along with people who are completely new to that and maybe have not known for comedy at all,” adds Wain. “That variety tends to make the whole ensemble feel fun and fresh.”
The film lets Deutch and the co-stars playing Gail’s entourage to embrace the sincerity of the hairdresser’s quest. “For the most part, the direction is to play it real and don’t go for the joke,” says Wain. “We feel like the craziness is plenty there in the words and the more that you just play the real scene as a real human, the funnier it will be.”
While Gail Daughtry and the Celebrity Sex Pass has a lot of fun serving inside jokes and playing into the magic of movies, Wain says he wasn’t trying to pull back the curtain on Hollywood’s dream factory, so to speak. “It was almost the opposite to work in the canvas of the Hollywood that exists in everyone’s perception and have our own fun riff on that and what Hollywood feels like to someone coming from far away,” he explains. “But then there’s inevitably [some of that] because we live here and are part of the world, but we had fun with things like the weird joke that the guy in the hotel would recommend a coffee place and it’s, like, Starbucks.” Gail and Otto naturally grab some grandes with wide-eyed wonder, with Otto finding a plum cruising spot that makes Gail blush.
If their innocence harkens back to an earlier time, Wain says that’s part of the film’s design. When I ask him about making a celebrity sex comedy in the age of #MeToo and whether Hollywood’s reckoning with handsy men made it difficult to tell these kind of saucy jokes, Wain says it wasn’t a factor. He notes that he and Marino wrote the film before #MeToo. Hollywood’s waning interest in comedy just accounts for Gail ’s long road to production.
“Comedy feature films in theatrical release have been essentially decimated,” Wain admits. “At a certain point studios were like, ‘Nope, we don’t do that anymore.’ Both for filmmakers and for audiences, that made devastating black holes. I’m hoping there’s a little bit of a turnaround happening and people are starting to realize comedy is in tough place.”
As audiences share a laugh together, Gail Daughtry offers a reminder that there’s no place like Hamm.
