Though perhaps difficult to detect at first glance, SIDEWAYS is the ultimate post-modern western whereby the two heroes are replaces by antagonistic antiheroes substituting their noble steeds for the dependable yet detestable wreck that is an oxidized red convertible.

The antiheroes? Meet Miles, a tragically depressed, failed novelists whose neurotically compulsive behavior seems an uncanny match for his cavalier, nonchalant college roommate Jack; the carefree flirt and debonair infomercial actor well past his golden age. Yet, friends they are, and friends they will remain, both before and after their unforgettable trip through California Wine country the week prior to Jack’s midlife wedding to Armenian heiress, Christine.

Hoping to send his friend out in style (note the lack of genteel manners from his own devious actions established early on in the film), Miles has big plans for Jack that include submersing him in the decadent culture of wine tasting and all its fine traditions, nuances, and... select wineries. Jack, the brash man with the palate of a two-year old, is hard-pressed to understand Miles' meticulous inspection of the tasty spirits. In short, Miles sips and Jack guzzles his way through the valleys of inland California, sampling the best of Pinot, Cabernet, and Syrah; with never the mention of Merlot unless to pejoratively damn its incompetent standing.

Meanwhile Jack has been concocting the ultimate Bachelor gift for both he and his best friend Miles: the gift of carnal knowledge. Despite the many adamant refusals from the high-strung Miles desperate attempts to cling to respectability amidst his mid-life crisis state (despite the obvious decline in gentility), Jack insists on an infidel affair that will be his final hurrah to the bachelor days of old. As Miles and Jacks adventures help them cross path with the fiery vineyard baron Stephanie, it isn't long before Jack has manifested multiple incidences where he can work all her angles; simultaneously allowing Miles to take his best shot at her lovely friend, wine virtuoso Mia. But Mile's discomfort with the latest news of his ex-wife's remarriage has set him reeling, and Mia seems the furthest thing from his mind, that is, until Mia insistently places herself in his depressing corners for reasons unbeknownst to the audience. All the while Jack and Stephanie have evolved into a saucy relationship that is as fast as Jack and Mile's expected trip. But shallow "I love yous" and empty promises of relocating and living with Stephanie and her daughter, have Miles shaking his head in disgust at the disloyal Jack who is still whole heartedly intent on marrying Christine.

The climatic moments of Mile's happiness and prospectively hopeful future with Mia are rapidly extinguished by his own blubbering goof and a swift visit from the vengeful Stephanie who has wrathfully beat the pulp out of Jack, and his beautiful face. It isn't until he is forced to run naked through menacing Ostrich fields and back to his hotel (for reasons not appropriate to disclose) that Jack finally realizes his stupidity and begins to understand his ill approach to the week's adventures. Determined to save his marriage, he enlists the help of the regretful Miles who, in a brief moment of courage, sneaks into a house and retrieves Jack's 'ill-placed' wallet, and together the two set out to wreck Miles' car in account of the narrative that will be constructed to explain Jack's newly broken nose.

A depressingly anti-climactic downfall progresses into depths of midlife crises' typical depression and self-loathing so attune to the fine abilities of human nature. Though Jack and Miles return safely to their humble abodes in San Diego, Jack to marry the next day, Miles, to continue hating himself, the depression for Miles sinks lower still, after news of his ex-wife's recent pregnancy and his latest rejected novel allow him to hit rock bottom. The solution? Opening his covetous 1961 Cheval Blanc and downing it in ample gulps alongside a greasy cheeseburger and fried onion rings. At his lowest moments one considers if all is lost, or will the sympathetic message from Mia prompt Miles to get his crap together once and for all? Can he ever pull himself out of the 'dark side' and begin living, or will the comforts of wine forever remain his only solace in life?

SIDEWAYS is an enjoyable relief from its contemporary pop-culture infested blockbusters. With acute detail paid to, not only the cinematographic and plot development conventions, the aura of wine and its bouquets, colors, aromas, legs, etc., are painted with as much detail as their equally colorful counterparts, Miles and Jack. The film is produced in a western meets seventies picaresque meets cult film genres with all of their thematic conventions working to develop a sincerely honest portrayal of two characters and their scathingly honest characterizations. Far from the regal heroes, Jack and Miles come loaded with flaws and shortcomings that are wholly embraced and shamelessly displayed for all of America to either judge, or simply delight in.

Also given much detail was an appropriately seventies-esque soundtrack and cinematography that compliment the more somber, melancholy score; the two conventions working together to draw out the eccentric characters of Miles and Jack: also adding to this effect are selective paintings hung in the backgrounds which mimic metaphorical characterizations of Jack and Miles' obvious flaws. But despite their pariah-like characters, it is as easy to love, as loathe, Jack and Miles for their faults that are garishly displayed in all their imperfect glory.

SIDEWAYS is a brutally honest film that delights in unveiling the true highs and lows of the common man and their trials and tribulations to overcome the everyday adversities that threaten to destroy our ultimate vision of happiness, so eagerly sought after, and so quickly stolen from our bird's eye's view.

Main Characters:

Miles, played by Paul Giamatti, is the pathetic, meandering failed novelist whose desperate attitude and actions borderline comical, yet detestable.

Jack, played by Thomas Haden Church, the slap-stick, slow-witted, animalistic and cavalier actor whose main goal for the week's trip is the sew his oats.

Mia, played by Virginia Madsen, the captivating wine-connoisseur and down-to-earth godsend that, for a brief moment, gives Miles something to live for.

Stephanie, played by Sandra Oh, the saucy vineyard employee who engages in a fiery-tempered, fast-moving affair with the lustful Jack.