sideways (2004)

two old friends set off on a wine-tasting trip that begins when miles, an aspiring novelist staring at wine and who has never recovered from his divorce, decides to give jack, his old college friend and actor, a gift to failed, a journey through the vineyards of the santa ynez valley, the week before jack's wedding. jack is an incorrigible and hyper-sexual seducer, while miles is a chronic, depressed pessimist. jack is looking for his 'last taste of freedom', miles, for his part, seeks perfection in a bottle. a jack any merlot, miles, instead, seeks the pinot of absolute perfection. as they venture onto the coast, miles and jack find themselves drowning in wine and women: jack falls madly in love with a winemaker, and threatens to cancel his marriage. miles, on the other hand, has a romantic encounter with a wine expert waitress: in short, both are on the verge of a mid-life crisis that is as dangerous as it is comic.