Will I turn into someone as pretentious, annoying and self-loathing as Paul Giamatti’s character in Sideways? I like to think I’m already there, and can go beyond how gratingly upset and miserable Miles is for the duration of this Alexander Payne directed piece. Considered to be one of the modern American classics, Sideways pairs up two somewhat likeable, yet wholly flawed characters, on a week of wine country exploration. Jack (Thomas Haden Church) is obsessed with having one last week of freedom before tying the knot, whilst Miles is still reeling from a divorce, a pending book deal and the general horrors of depression and anxiety that plague his life.
Sideways has that delightful charm to it, where it throws us right into the middle of two characters we know nothing about. Payne’s ability to create interesting characters and pave the way to a rather resounding, open-ended conclusion is one of the many strengths his storytelling style has to offer. Miles and Jack are exceptional, well performed by Giamatti and Church, who hold a great deal of back and forth chemistry with one another. Giamatti steals the show, though, with his consistently aggravated demeanour, a furrowed brow in even the most delightful and engaging of times. It’s clear from the get-go that he’s close to snapping, and the film piles the pressure on thick time and time again.
It makes for a clean break away from the expected, trivial nature of most light-hearted romantic drama films. There are those ups and downs throughout, but they feel rather nuanced and small in comparison to the astronomical levels of character development put on display by our leading duo. Sideways revels in its ability to not have entirely likeable characters, flaws that can push an audience to the edge of really wanting to see them fail, an oddly effective way of keeping an audience invested, to see if they’ll stick around for a sour-tasting ending. The film veers on the side of pretentiousness from time to time, recycling the same few talking points for the many characters we find ourselves interacting with. Self-loathing individuals, mulling around, tasting wine and generally being horrible behind one another’s backs. They walk a fine line between charming and condescending, and that line blurs a little too much from time to time.
Where the film falls apart though is within the comedy it looks to present. I’m no friend of most American comedies, but here the offerings are limited at best. There are a few extraordinary moments littered throughout, and thankfully they make for the most memorable of scenes. Giamatti sprinting away through a vineyard whilst necking a bottle of wine, Church windmilling a golf club around his head whilst running after a golf buggy, and generally just some nice dialogue and wordplay between the two. These scenes feel few and far between, though, engulfed by some moments that fall flat, or some that look to involve Virginia Madsen and Sandra Oh a tad more. The four makes for a great ensemble, and with some tweaks to the adaptation of this Rex Pickett fiction, Sideways could’ve elevated itself to some masterful moments.
Toiling in misery for most of its running time and wrapping up with one final, bittersweet moment, Sideways has strong character studies that unfortunately fall into a loop of recycling the same few plot details over and over again. It’s certainly interesting, but it leaves a lot to be desired when these two characters feel so vivid and well performed. Interactions with their surroundings all feel realistic, as do the supporting characters, but for many of the scenes, the humour falls a tad flat, leaving in its weak some very enjoyable, albeit insubstantial dramatic subplots.