The first film I know of that can be called a "wine lover's movie", Sideways is a simply told but morally complex comedy about two fortyish Southern California men – Miles (Paul Giamatti), a stifled writer, and Jack (Thomas Haden Church), a floundering actor – who spend the week before Jack's gloomy-looking wedding to explore Santa Barbara County's wine region, tasting the wineries' latest offerings, playing golf, and male-bonding. But it quickly becomes apparent that Jack's primary goal for the week is to get Miles – and, more importantly, himself – laid. While the self-righteous Miles sneers at the flaky Jack for cheating on a fiancée whom he obviously doesn't care much about, he himself is freaking out over his ex-wife's new marriage, the unlikely future for his epic unpublished novel, and his own reluctance to romance a woman who seems perfect for him (Virginia Madsen).
What follows is an often funny, squirm-inducingly real look at two losers – an uptight nerd and an oversexed himbo, an Odd Couple for the aughts – each finding himself neck-deep in midlife crisis.
Good work all around from a quartet of often-overlooked actors (Sandra Oh – the director's own recent bride – rounds out the foursome as Jack's free-spirited "conquest"), with detailed, authentic set design and a jazzy score. But this film, like all of Payne's, is all about the script. Payne and his longtime writing partner Jim Taylor have established a routine of loosely adapting little-known novels (see also Election and About Schmidt) to tell painfully truthful tales about pathetic men and unforgiving women. It's a bleak worldview, one in which the bad go unpunished (though their victories may be Pyrrhic), and the good – or at least the slightly more redeemable – only find happiness by giving up on their dreams and accepting their insignificance. Which is so blunt that, in the end, it may be hard for many to find these films entertaining. But Payne and Taylor aren't pessimists. They constantly challenge the audience to look into their own hearts to find sympathy for characters that may be profoundly unheroic, even downright unlikeable, but are the same people we forgive and tolerate on a daily basis: our friends, our families, and ourselves.