Sideways starts with two old friends setting off on a wine-tasting road trip... only to veer dizzily sideways into a wry, comedic exploration of the crazy vicissitudes of love and friendship, the damnable persistence of loneliness and dreams and the enduring war between Pinot and Cabernet. The misadventures begin when Miles (Paul Giamatti), an un-recovered divorc? and would-be novelist with a wine fixation, decides to gift his old college buddy and washed-up actor Jack (Thomas Haden Church) with a celebratory trip to the vineyards of the Central Coast the week before Jack's wedding. The two couldn't be an odder couple. Jack is an over-sexed charmer; Miles is a sad-sack worrier. Jack is looking for his "last taste of freedom;" Miles is just hoping to not get even more depressed. Jack is fine with cheap Merlot; Miles pines for the perfect Pinot. Indeed, the only thing they seem to share in common is the same heady mix of failed ambitions and fading youth. And yet, as they make their way up the coast, Miles and Jack soon find themselves drowning in wine and women (Sandra Oh and Virginia Madsen). When Jack falls head-over-heels for a local wine pourer and threatens to call off his nuptials, Miles tries to keep his friend on the straight and narrow. But Miles's own romantic encounter with a wine-savvy waitress interferes and sends them both careening headlong into reality. Now, the wedding approaches and with it the certainty that Miles and Jack won't make it back to Los Angeles unscathed or unchanged... if they get there in one piece at all.
2hrs 20min long
Thomas Haden Church