The misadventures begin when amateur wine enthusiast Miles (Paul Giamatti) decides he's going to take his old college buddy the charming Jack (Thomas Haden Church) on a relaxing trip to the vineyards of California's Santa Ynez Valley the week before Jack's impending nuptials. It would be nice if it were that simple but in actuality the two comically mismatched friends have some serious mid-life crises to work through: Miles is a sad-sack worrier who has been depressed for the last two years over a failed marriage and several failed attempts to get his novel published while over-sexed Jack faces his faded youth and fading acting career. Their journey denigrates into debauchery as trips like this is are wont to do and Miles and Jack soon find themselves sniffing swirling and downing wine while chatting up the local denizens--including the vivacious wine pourer Stephanie (Sandra Oh) to whom Jack takes a shine and the quiet wine-savvy waitress Maya (Virginia Madsen) who takes a shine to Miles. At the end of the week the guys eventually emerge from a haze of pinot noir sexual escapades and wistful yearnings to collide with the reality of heading back home.
Payne didn't want to cast what he calls "movie stars" for Sideways deciding to go with lesser known actors who could bring out the human drama in a more instinctive way (even though Payne probably could have brought out good performances in just about anyone; look what he did with Jack Nicholson in About Schmidt). Casting the superb Giamatti as the beleaguered Miles however is a stroke of genius: The actor elevates the movie to another level turning in an unbelievably heart-wrenching performance. Sure Giamatti is the king of playing losers having played plenty of them in his career (American Splendor Duets) but it's the surprisingly sweet and gentle way he becomes the guy who maybe just maybe gets the girl that knocks you out. Madsen as Miles's would-be paramour Maya also comes out of nowhere to give a very genuine portrait of a woman who's dealing with her own divorce while looking for some companionship. The actress has finally been given the chance to shine after a lot bad television (anyone remember
Just Ask My Children? My point exactly) and the movie's the better for it. As the other two players in the quartet Church whose been out of the loop since his days on TV's Wings does a wonderful job as Jack the cad who actually has a heart while Oh (Under the Tuscan Sun) adds a nice touch as the gullible Stephanie just looking for Mr. Right.
How about these quirky indie writer/directors these days getting all mushy and romantic? Charlie Kaufman started the trend this year with his terminally hip but eternally tender Eternal Sunshine of the Spotless Mind and even David O. Russell's I Heart Huckabees has its gooey moments weird and existential as they were. Now it's Alexander Payne's turn--and he's hit the jackpot. Based on the semi-autobiographical novel by Rex Pickett Payne along with writing partner Jim Taylor has crafted another exquisite slice-of-life movie to follow his brilliant efforts About Schmidt Election and Citizen Ruth but has also delved into the heart-ripping love story genre; Sideways is so painfully aching at times it hurts. The characters give eloquent soliloquies rather than come off as just talking heads spouting dialogue--Maya's explanation on why she loves wine so much; Miles' take on the delicate beauty of the pinot noir grape; Jack's tearful pleading with his friend to save him all hit home. Then of course there's the wine. Payne so vividly paints the artistry the tastes the pure love of wine as well as stylishly filming California's wine country that connoisseurs and novices alike will appreciate this movie. Heck anyone who just likes to drink the stuff is going to be mesmerized by the intimacy of it all. Speaking of which where's that bottle opener?