Miles (Paul Giamatti) is a middle-aged high school English teacher who is at his wit’s end. He has recently written a novel and is anxiously awaiting to hear a verdict as to whether he will be able to publish it. To get his mind off his daily distractions, Miles recruits his best friend, Jack (Thomas Haden-Church), a failed actor, to accompany him on a week-long trip to the California wine country, where they’ll spend a few days sampling some of the region’s finest wines and playing golf. Jack is about to get married, but his rambunctious spirit from years of being a desirable lead in a soap opera years before has meant that he has absolutely no qualms with being unfaithful, as long as whoever he’s with is aware that it’s only for a few days. This takes the form of Stephanie (Sandra Oh), a local vintner who finds herself feeling the same passion to this mysterious, yet oddly confident, washed-up star. Meanwhile, Miles’ eye is caught by Maya (Virginia Madsen), a waitress at his favourite wine-country restaurant who reveals herself to be quite an enigmatic figure, a person constantly in search of some sense of belonging, much like Miles himself. For a few days, the duo gallivants throughout California’s most beautiful landscapes, engaging in a series of mischievous adventures, and narrowly avoiding trouble as much as they can – which is certainly not much for these two old friends trying to abandon their routine and lose their stifling inhibitions for a few days.

Sideways is a time capsule of a film – not necessarily dated, but rather indicative of a particular period of independent filmmaking that reached its apex in the early 2000s, and where the idea of two slackers on a road trip wasn’t only acceptable, it was absolutely riveting. Made when Alexander Payne was still quite an audacious filmmaker capable of extracting extraordinary emotion from the most unconventional situations, it forms part of a series of films in which the director looked deep into the human spirit, something he has touched on in subsequent films, yet not with quite the same sincerity as it was done here. Perhaps not as biting a comedy as Election, or as profoundly moving as About Schmidt, the film is quite an entertaining adventure that looks into many different themes with elegance, good-natured humour and a lot of heartful sentimentality that prevents it from ever descending into outright sardonic chaos, on the precipice of which it constantly appears to be standing, verging on eruption that may be pleasing to those seeking the kind of outrageous entertainment a film like Sideways would normally offer based on the premise, but contrary to the more tender soul underpinning the story.  

The road trip film has existed as a genre on its own for decades – and whether coming in the form of the most poignant drama or hilarious comedy, it has been somewhat embraced almost universally, with the idea of one or more people embarking on a journey to a particular destination being interesting enough in terms of offering us both a compelling story, and a change of scenery that prevents the kind of banality that often comes when looking inward, as these kinds of films tend to do quite regularly. However, Sideways does go about subverting some conventions associated with the sub-genre without necessarily deviating from the core of what makes this kind of film so special. Payne has constructed an acidic dark comedy that presents us with a pair of vaguely unlikable protagonists who are in the throes of middle-age and trying desperately to fight out against the inevitable physical and mental decline that they know they are quite close to experiencing. Their idea of escaping fate takes the form of a Californian road-trip, in which they’re able to abandon their domestic life and go in search of momentary satiation from reality. However, the conflict comes in the traditional method of dismantling the well-conceived schedule and presenting us with a series of misadventures and incidents, where nothing goes according to plan, which is where the comedy is derived. Naturally, Sideways is far from being this myopic, and it manages to provide some profound commentary without becoming overwrought or preaching, but rather finding the delicate balance between humour and pathos, which makes it quite an effective work of independent comedy, where we are invited to laugh in situations that don’t normally evoke much joy.

Sideways is often remembered as a film that works mostly as a great ensemble piece, with the cast being kept relatively small, and focusing on only four main characters. Leading the cast is Paul Giamatti (a truly great actor, but one who also defines a particular era in filmmaking), giving one of the many performances where he plays a middle-aged man in some kind of crisis. No one can bring such charm to a bundle of neuroses quite like Giamatti, who seemed to be pandering to the idea of some Midwestern Woody Allen in these kinds of roles, endearing without being particularly likeable. He’s sharply contrasted by Thomas Haden Church, who plays the self-confident, cocksure Jack, an actor who refuses to acknowledge his irrelevance, coasting off a popular performance from decades before, still believing himself to be a highly sought- after actor – from Jack’s perspective, the lack of offers speaks more to his apparent exclusivity, rather than the fact that he is almost entirely forgotten, a living piece of trivia rather than the adored performer he believes himself to be. It takes a lot to steal the show from Giamatti in this kind of film, particularly because he flourishes with these low-key, quaint independent comedies that rely on his enduring everyman nature. However, Haden Church does remarkably well and ends up truly being the most memorable part of the film.

Virginia Madsen and Sandra Oh round out the ensemble, with Madsen being astounding as Maya, the endlessly adorable waitress who yearns for a better life. She is the most natural performer in the film, bringing such authenticity to everything she’s given to do, even the most ludicrous dialogue, or some questionable character choices. The same can’t really be extended to Oh, who is terrific as usual but has the challenge of being given a character who isn’t much more than a plot device, a secondary archetype that doesn’t really get much space to develop on her own. She does bring a certain cheekiness to the role, but its a far cry from the immense talents she has shown subsequently. Something very important about this kind of film is that it touches on some major subjects, but in a more intimate manner, which requires a strong screenplay. This is undeniably Sideways‘ most significant merit, particularly because everything this film has to say, it does through the dialogue. It also fell on the actors to bring their own interpretation to these characters, with their strong performances and incredible chemistry bolstering the film and preventing it from ever becoming self-indulgent or pretentious in any way, a major concern with films of this kind, where the inner psychological machinations of the characters are sometimes unbearable. This film effectively does what so many others have failed to do – it pays attention to its characters and gives them enough to work with so as not to be wasted, but also never requiring them to play to some stereotype, which appears to be the direction they’re heading from the outset, which is proven false when we notice how much care was taken in constructing these characters.

Thematically, there is much more to Sideways that just two men gallivanting through wine country and encountering mischief along the way. There’s a lingering sense of melancholy that pervades the film, particularly in regards to the theme of ageing. This film would not have had the same impact had any other kind of character occupied the two central roles, particularly because so much of the film depends on the discourse surrounding middle-aged mediocrity, and how it’s channelled through the two main characters, who grapple with their own shifting masculinity, finding themselves occupying very different societal positions than they’d like to admit as being true. Ultimately, the film is commenting on these two characters by contrasting them – Jack is past his prime, while Miles is still looking for his, and the film explores their friendship in a way that it’s able to provide insights into the minds of these characters constructing them as realistic individuals rather than simply entertaining figures derived from a series of unrealistic quirks. The film is certainly not the definitive text on any of these themes, and it can be clumsy in how it perceives some of the ideas it proposes itself as being remarkably adept at. However, it is evident that Sideways does do exceptionally well in finding the humanity in a group of individuals that could’ve easily just been played for laughs, but through the delicate approach to the subject matter, it turns out to be quite unexpectedly touching. Sideways starts as a broad comedy, but funnels out all the aggressive, over-philosophical content that weighs it down, and ends as a touchingly human drama, which creates a memorable work of independent cinema. Funny, heartfelt and poignant, Payne made a terrific film that understands and embraces its confines, which is more than enough for such an intimate character study, which seeks to provide insights rather than evoke immensely complex discourse, which would have been misguided in an otherwise tremendously enjoyable film.