When her fiancé Tom (Michael Cassidy) cashes in his celebrity hall pass in the back room of a local bookstore, poor Gail Daughtry (Zoey Deutch) is heartbroken. What was once a whimsical thought exercise has now become very real. The only way to make things right is for her to even the score with her famous crush, Mad Men hunk, Jon Hamm. It won’t be easy, but nothing worthwhile ever is in David Wain’s Gail Daughtry and the Celebrity Sex Pass.
Co-written by Wain and Ken Marino of The State and Wet Hot American Summer fame, Gail Daughtry and the Celebrity Sex Pass is a loving and knowing nod to the glamour and nonsense of Hollywood. The film takes a ridiculous tour of Tinseltown through the eyes of a small-town girl with big dreams as she and a growing cohort of goofball supporters make their way toward Hamm’s bedroom with stars in their eyes and love in their hearts.
Fans of Wain’s previous films will find a lot to love in this unabashedly silly film, which hews close to the tone of his last feature, They Came Together, while still managing to remain surprisingly chaste, despite the film’s eyebrow-raising title. Where Wet Hot was a loving take on the summer camp comedies of the early ‘80s and They Came Together tackled the ‘90s rom-com wave, Gail Daughtry and the Celebrity Sex Pass acts more like a supersized mix between The Wizard of Oz and a Cannonball Run movie, a combination I never knew I needed.
Thankfully for the blissfully naïve Gail, she collects a cadre of oddball friends who help her along the way. In what seems like a kismet, she sets off for Hollywood to attend a stylist convention where the star guest is hair impresario, Remy Fontaine, portrayed here by a magnificently coiffed Thomas Lennon. She grabs her co-worker, Otto (Miles Gutierrez-Riley), and they are off to the races.
A trip to the Creative Artists Agency nets them office assistant Caleb (Ben Wang) to help guide them through the biz. Also along for the ride are frustrated former paparazzo Vincent (co-writer, Ken Marino) and the real key to the Hamm puzzle, his former Mad Men co-star, a dizzyingly fun John Slattery as himself. These core five characters ping pong through Hollywood in an attempt to find Hamm and give Gail exactly what she’s been looking for, but it’s not going to be that easy.
Between Gail and a night of passion with her hunk are a series of hilarious obstacles that she must overcome. There are crossed wires when she attempts to break into Hamm’s property only to learn that it’s actually the home of a very different, very weird superstar; there’s a hilarious side plot involving gangsters led by Ludovica (Sabrina Impacciatore) with Joe Lo Truglio (Brooklyn 99) as an idiot henchman; and even when they do eventually track down Hamm, they have to get through his personal security guard, Terrence (Tobie Windham), who makes one of the most horrifying threats I’ve ever seen in a film.
However, Gail is a go getter, and though the journey is arduous, she’s not going to give up. Genuinely one of the funniest, most heart-warming, and most joyous films about infidelity I’ve ever seen, Gail Daughtry and the Celebrity Sex Pass does everything right. Not only does the film endear us to an ever-growing crew of the most ridiculous characters ever assembled on film, but it also delivers jokes at a dizzying pace with each moment more gloriously absurd than the last. Between this and last year’s Naked Gun remake, I have grown increasingly hopeful that the age of comedy has returned, and I’m ready for it.
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