Sideways (2004) is a hilarious and often wistful comedy-drama starring Paul Giamatti as Miles and Thomas Haden Church as Jack—college roommates and lifelong friends now eking out disheartening lives as a failed author/English teacher and a fading soap opera actor, respectively.
As their lives have turned toward mediocrity and middle age approaches, Jack prepares to finally settle down to marriage—but not before Miles recruits him for a week-long tour of California's Santa Ynez Wine Country. Miles' plan for a proper getaway to immerse them both in good wine and male bonding are undermined, however, by Jack’s intentions of scoring one last sexual tryst before settling into domestic existence.
Co-written and directed by Alexander Payne (About Schmidt, Nebraska) and based on the novel by Rex Pickett, Sideways is ostensibly a film about wine and Miles’ humorously haughty attitude as a full-fledged wine connoisseur. At the same time it’s a touching parable about the aging process and personal reckoning—capturing that disorienting period of time when men enter genuine adulthood and often resist the inevitable ebbing toward the latter stages of life. A fine mix of the sweet and the sour, replete with genuine smarts, pointed drama and a number of laugh-out-loud moments.
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