A scene from ‘Gail Daughtry and the Celebrity Sex Pass’

Gail Daughtry and the Celebrity Sex Pass review: Fellowship of the fling

‘Gail Daughtry and the Celebrity Sex Pass’ is a hilarious comedy that follows a small-town hairdresser’s quest to bed her Hollywood crush.

Everyone has fantasies about public figures. Athletes, actors, politicians — if you see them and think they’re attractive, you can dream about them. This appeal is what Hollywood box offices are built on. Casting the “It” guy or girl of the moment is a way to get butts in seats — especially when a movie doesn’t have much else to offer. We play games like “F@*k, marry, kill” or make pacts predicated on impossible situations. But no one ever expects to have to make these choices in real life. That’s what makes Gail Daughtry and the Celebrity Sex Pass so intriguing.

Weeks before her wedding to Tom (Michael Cassidy), Gail (Zoey Deutch) didn’t think anything could ruin her big day. On their way to Jennifer Aniston’s book signing, Gail mentions the celebrity sex pass. After insisting they could never imagine being with anyone else, Tom and Gail agree their free passes are Tilda Swinton and Jon Hamm, respectively. That is until Tom jumps on the Aniston bandwagon and replaces Swinton. When Gail finds Tom redeeming his freebie, the small-town hairdresser takes off to Los Angeles for the weekend with her best friend, Otto (Miles Gutierrez-Riley). While there, she decides the only way to save her relationship is to even the score: she must have sex with Jon Hamm.

Even if the goal is unusual, this is fundamentally a quest-based adventure film. It begins with two companions in a foreign land with an impossible task. Each stop in their journey adds a new ally to their fellowship: an overzealous Creative Artists Agency (CAA) receptionist (Ben Wang), a well-intentioned paparazzi (Ken Marino) and Mad Men star John Slattery (himself). It’s surprising how many people are willing to take up Gail’s unusual and very personal cause. It’s as if making her dream a reality will give hope to people around the world — if she can do it, then maybe they too could redeem their celebrity sex pass.

Most people have heard of this kind of pass or freebie list. It usually consists of one to five people who are out of reach. The idea is if someone implausibly has sex with a person on the list, their significant other “cannot” be upset. But it’s more like a fun game to play with your partner or friends — not a conceivable circumstance that will test the strength of your relationship. It’s especially amusing that Aniston is at the centre of this controversy since her former TV series, Friends, also dedicated an episode to the freebie list.

They design every aspect of this film to be absurdly funny. The tongue-in-cheek dialogue pokes fun at everything from the commercialization of Hollywood Blvd to people not understanding the difference between “sympathize” and “empathize.” They even make normal situations ridiculous. Aniston reads from her cookbook, an instant stain remover pen cleans up a blood-soaked mess and a chance encounter with ‘Weird Al’ Yankovic ends with him chasing the group with an AR-15, which couldn’t be more against type. Whenever Otto tries to be reasonable or bring logic into the conversation, everyone quickly shuts him down. The comedic timing is impeccable and it all comes together because they’re all playing it straight.

To add a sense of danger to the story, they use the classic switched briefcase caper. When the inept gangsters realize their mistake, they spend the film tracking Gail and Otto around the city. Yet, the case’s contents are not even the standard valuable object one would expect to find.

As the film progresses, it becomes apparent that it will continually defy expectations. Even when the film’s direction seems predictable, the characters will say or do something surprising. In addition, there are many cameos sprinkled throughout the picture. Of course, the movie doesn’t work without Slattery and Hamm being all in to play these silly versions of themselves.

For a group of random people, the fellowship repeatedly gets shockingly close to Jon Hamm. Yet, Gail is so kind and earnest, it’s hard to believe she’d go through with it if she found him. But it’s definitely worth watching to find out.

(Side note: Jon Hamm is always referred to by his full name — it’ll make a dangerous drinking game when released for home viewing.)

Director: David Wain
Starring: Zoey Deutch, Miles Gutierrez-Riley and Ben Wang

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