David Wain has never been a filmmaker interested in subtlety. From Wet Hot American Summer to Role Models and Wanderlust, his comedy thrives on committing fully to absurd ideas and pushing them well beyond the point of reason. With Gail Daughtry and the Celebrity Sex Pass, he may have delivered his most gloriously ridiculous film yet – a laugh-out-loud, slapstick-heavy riff on, of all things, The Wizard of Oz.
The premise is delightfully simple. Gail Daughtry (Zoey Deutch), a small-town Kansas hairdresser, discovers that her fiancé Tom (Michael Cassidy) has unexpectedly used his celebrity “hall pass” after a chance encounter. Devastated but determined to restore cosmic balance, Gail heads to Los Angeles with a singular mission: track down her own celebrity pass, Jon Hamm, and sleep with him. What follows is a wildly unpredictable journey involving talent agents, washed-up celebrities, suitcase-swapping assassins, psychics, paparazzi and enough celebrity cameos to keep audiences constantly scanning the screen for familiar faces.
What makes the film work isn’t the premise itself but Wain’s complete commitment to the bit. Gail Daughtry and the Celebrity Sex Pass operates with the manic energy of a live-action cartoon, throwing jokes at the audience so rapidly that it’s impossible to catch them all on a single viewing. Some gags land harder than others, but the sheer volume and confidence behind them creates an infectious momentum. The film often feels like a modern descendant of the Zucker brothers’ comedies, embracing silliness with a sincerity that becomes increasingly charming as the story unfolds.
The secret weapon is Deutch. Long one of contemporary comedy’s most underrated performers, Deutch gives Gail an earnestness that keeps the increasingly ludicrous plot grounded. She treats her mission with the seriousness of a hero embarking on an epic quest, and that unwavering commitment makes every absurd obstacle funnier. Gail may not always be the brightest person in the room, but Deutch ensures she’s always the most lovable.
As entertaining as Deutch is, the film’s MVP may well be John Slattery. Playing a heightened, deeply pathetic version of himself, Slattery spends much of the movie wrestling with his perceived status as Hamm’s less successful Mad Men co-star. The performance is a masterclass in self-deprecation, with Slattery gleefully dismantling his own image through increasingly unhinged dialogue and physical comedy. Whether he’s delivering outrageous one-liners (“I like my women like I like my men. Chunky as fuck!”) or enduring slapstick punishment worthy of a silent comedy star, he consistently steals every scene he enters.
Hamm proves equally game, portraying himself as a surprisingly insecure celebrity hiding behind a carefully curated public image. The dynamic between Hamm and Slattery becomes one of the film’s most rewarding running jokes, particularly for viewers familiar with their shared television history.
The supporting cast is truly an embarrassment of riches. Ben Wang emerges as a standout as Caleb, an overconfident talent agency assistant whose misplaced self-belief provides some of the movie’s biggest laughs. Miles Gutierrez-Riley brings warmth and charm as Gail’s loyal companion Otto, while Kerri Kenney-Silver nearly walks away with the entire film in a brief but unforgettable appearance as the psychic who sends Gail on her quest. Meanwhile, familiar faces from Wain’s comedy universe pop up throughout, creating the sense of a filmmaker gleefully inviting his friends into the sandbox.
Beneath all the celebrity jokes and escalating absurdity lies an unexpectedly clever framework. Wain essentially reimagines The Wizard of Oz through the lens of Hollywood culture, with Gail’s journey through Los Angeles mirroring Dorothy’s trip through Oz. The parallels become increasingly apparent as the film progresses, adding another layer of amusement without ever overwhelming the comedy.
The film’s relentless pace occasionally threatens to outrun itself. The first half barrels forward at such speed that some plot points barely have time to register before the next gag arrives. Yet even when the narrative becomes gloriously chaotic, Wain never loses sight of what matters most: making the audience laugh and ensuring they’re having a good time.
Most importantly, Gail Daughtry and the Celebrity Sex Pass understands something many modern comedies have forgotten. Sometimes being funny is enough. In a cinematic landscape increasingly dominated by self-serious prestige projects and irony-soaked humour, there’s something refreshing about a movie that simply wants to entertain. It’s loud, silly, proudly stupid and completely unconcerned with appearing clever.
By the time a delightfully bonkers finale arrives, complete with one last payoff to the film’s Wizard of Oz influences, you’ll likely find yourself smiling as broadly as the characters on screen. It may not be profound, but it’s a reminder of how joyful comedy can be when talented performers and filmmakers are given permission to go completely off the rails.
Gail Daughtry and the Celebrity Sex Pass is gloriously stupid in the best possible way – a big, broad, unapologetically silly comedy powered by an excellent ensemble cast, a game-for-anything Deutch and a scene-stealing Slattery. Sometimes the craziest solutions really are the most sane.
THREE AND A HALF STARS (OUT OF FIVE)
Gail Daughtry and the Celebrity Sex Pass is screening as part of this year’s Sydney Film Festival, running between June 3rd and 14th, 2026. For more information on session times and ticket sales, head to the official site here.
