Everyone has their list of dreams, which can range from the ambitious to the outright unrealistic. In either case, even those who may not necessarily pursue a particular goal still can enjoy the very idea of it, especially when it comes to the more scintillating and potentially controversial of them. Many couples have what are known as “hall passes”, usually celebrities who they (in what is almost always a joke) agree the other has their full permission to pursue if given the opportunity. It’s more of a parlour game than anything else – but what if there was a situation where it truly came to fruition? This is what we find to be the foundation on which David Wain and Ken Marino build Gail Daughtry and the Celebrity Sex Pass, their irreverent and bitingly funny satire in which the idea of infidelity being acceptable granted it is with a world-renowned celebrity, takes the focus. The story revolves around the titular character, a young woman as gullible as she is ambitious. After she finds that her soon-to-be-husband has engaged in a momentary affair with his “hall pass” (who happens to be Jennifer Aniston), she sets out to satiate her own desires, which come in the form of Jon Hamm, about whom she’s always had feelings. Travelling across the country from working-class Kentucky to the sprawling metropolis of Los Angeles, Gail (accompanied by her best friend Otto) sets out to find Hamm so that they may hold up her end of the bargain, not being entirely aware of the fact that simply starting a romantic relationship with someone of his stature (or frankly just about any celebrity) is not as easy as it seems, especially not when they encounter a range of eccentric characters, most of whom become obstacles in their journey. A hilarious and offbeat comedy that never takes itself particularly seriously, while still managing to be quite moving in a few small but significant ways, Gail Daughtry and the Celebrity Sex Pass is a real gem of a film, the kind of off-the-wall comedy that can only come from a collective of humourists who have mastered their craft, and are bursting at the seams to share their peculiar observations with the audience.
There are some ideas so absolutely unhinged and absurd that we cannot fathom them being the foundation of any legitimate piece of art – which is why this concept fell into the hands of Wain and Marino, who have built their careers on precisely this kind of off-the-wall madness. Some feel that their comedic collective, which emerged in the late 1990s, has played a vital role in the formation of contemporary comedy, not only due to the presence of several collaborators who would go on to become stalwarts of the industry in their own right, but also because the genre shifted slightly once their devil-may-care attitude to humour was unleashed onto unsuspecting audiences. The general rule of thumb when exploring work by any of its founders or close collaborators is very simple: don’t only expect the unexpected, openly anticipate it, because you’re bound to find something to enjoy, even if it does tend to push boundaries a bit too far at times. Gail Daughtry and the Celebrity Sex Pass is one of the many instances where Wain crafts a film from a very simple premise, and one that is certainly not unique to him or his cohorts. It seems like every couple, at some point or another, engages in the lighthearted conversation about who the one person is for whom they will be willing to suspend the promise of faithfulness with the other’s permission, and this film puts this principle into practice by looking at someone who takes this as an invitation rather than just a fun thought experiment. It is from this that Wain builds what proves to be an unexpectedly fascinating exploration of celebrity culture, something that takes on even more meaning when we consider Gail Daughtry and the Celebrity Sex Pass is coming after decades of the director being involved in the industry, but where he is still something of an outsider based on the work he does not quite fitting with the mainstream. The result is a hilarious deconstruction of Hollywood from the inside out, a brutally funny depiction of the cult of fame and how shallow this industry can be – and in between these bold swings, it also finds time to be genuinely moving, which is certainly surprising but not entirely unexpected considering the story being told.
Over the last couple of decades, Wain and Marino have drawn in some exceptionally talented actors, many of whom had their big breakthroughs as a result of these collaborations. However, as they’ve grown more notable, we’ve seen more established names also entering the fray, usually leaping at the opportunity to collaborate with a director and writer who have been adamant in creating memorable parts for any actor willing to take the journey with them. Gail Daughtry and the Celebrity Sex Pass is led by Zoey Deutch as the titular character, a young woman who sets out on a nearly impossible journey, not realising that what she is attempting to achieve is not likely to happen – but because logic is always malleable in film, she gets exactly what she was looking for, which is all part of what makes the film so hilariously strange. Deutch is a very gifted performer, someone who has consistently proven herself to be capable of delivering work that is both funny and moving – and she certainly has her work cut out for her with this part, which requires her to play a predictably eccentric character, albeit in a way that is always quite surprising, even at its most obvious. She’s joined by an ensemble cast that includes Miles Gutierrez-Riley as Otto (and who is regularly the funniest part of any scene he is in), Ben Wang, Marino and, in a strange bit of casting, John Slattery as a fictionalised version of himself, a sad-sack slacker who yearns for his glory days. They make for an unexpectedly strong ensemble, and are joined by a cavalcade of notable names in very brief roles, including Hamm, who also proves that, despite most of his acting work being quite dramatic, he has impeccable comedic timing that fits in perfectly with what this film is trying to say; his arrival in the final act not only brings an end to that specific part of the story, but also contains the kind of aloof charm that has always driven so many of his greatest performances. It’s a strong, reliable cast that understands the assignment from the foundation, delivering stellar work that requires so much from them as performers.
When handling such a strange subject (and the wide range of eccentric personalities that accompany it), it is obvious that Gail Daughtry and the Celebrity Sex Pass needed to find the right balance between tones in order to be considered at least partially effective. Mercifully, Wain has always made it clear that he’s someone with a firm grasp on exactly what makes audiences laugh, and this film is not an exception by any means. When faced with the choice between authenticity and absurdity, one would assume that the former would be preferable – but few artists have been more committed to the pursuit of unhinged madness more than Wain, who has returned from an unusually long sojourn from the medium (his previous directorial outing being the wonderful A Futile and Stupid Gesture, nearly a decade ago) with this triumphant, irreverent comedy that never, for even a moment, comes across as being intentionally sincere. Like many of his previous works, Gail Daughtry and the Celebrity Sex Pass takes a simple premise and reworks it into something unquestionably strange and frankly a bit unsettling, which is all part of the incredible appeal of this film, and the primary reason it ends up working so exceptionally well. There is a very narrow boundary between humour that is provocative and edgy, and that which is vulgar just for the sake of getting a reaction. This film walks that tightrope brilliantly, being able to push along the edges of decency without ever becoming excessive or inappropriate – in fact, the more peculiar overtures (such as the random diversions into hardcore violence) are effective because of how unexpected they are, since we don’t usually anticipate such a happy-go-lucky comedy from being this dark, something that the director and his team use to incredible effect. The humour itself feels appropriately strange, existing at that peculiar intersection between bawdy and intelligent, which is what gives it such a unique identity – a smart, satirical jab can occur in between a fart joke and a slapstick pratfall, and it will all seem entirely natural in the context of the film being made.
What you see is what you get with Gail Daughtry and the Celebrity Sex Pass, a film that is wickedly funny and deeply unnerving in equal measure, which is precisely what we would hope would be the outcome of such a strange and offbeat comedy. There’s an elusive quality that makes this so incredibly compelling – a lot of modern comedy tends to be built from the idea of making something as relentlessly wacky as it can be, but very few seem capable of actually saying something of value. However, at no point does the film intend to be preaching to the audience about any issue – in fact, its complete incredulity towards meaning, and its adamant refusal to find a moral amongst all this madness is exactly why it is such a remarkable achievement, since it has nothing to prove other than that it can make any situation not only funny, but outrageous and provocative, even at its most simplistic. It goes in a few predictable directions, but it is (for the most part) a very original experience, an irreverent dark comedy that is very liberal with how it portrays its characters (helped immensely by a tremendous cast), taking them on a fascinating journey that is as strange as it is deeply captivating, which may not be easy to predict for those who aren’t entirely attuned to the stranger components that drive this film. It is ultimately a far more engaging film than we may expect, much more than just a silly comedy revolving around sex (in fact, the act itself is relatively minor, being used only as a brief source of humour at different points), and instead focusing much of its efforts on being an off-the-wall character study about eccentric people gathering to accomplish a single goal. It’s about as unrealistic as such a film can get, but this is ultimately all part of the experience, making Gail Daughtry and the Celebrity Sex Pass one of the year’s most peculiar but unquestionably entertaining comedies.
