The movie invites us to be road trip companions to Jack and Miles. Jack (Thomas Hayden Church) is getting married soon and best man Miles (Paul Giamatti) has planned a week of male bonding through golf and wine tasting. Miles is a man of culture, who has a series of procedures before he even tastes the wine. Jack is rather impatient and easily quaffs the liquid. He’s more concerned with the alcohol taking effect rather than what flavor is hinted on the taste. Jack is your basic fun-searching horndog, only more immature. Jack’s idea of male bonding is for both of them to bond sexually with women along the trip.
And yes, as if the gods granted Jack’s wishes, we meet two women along the road. Maya (Virginia Madsen) is a waitress in a bar/restaurant whom Miles frequently visited. We sense that Miles sees Maya as someone to secretly pine for but could never touch because she’s married and he is too depressed even she’s not. Stephanie (Sandra Oh) is a wine pourer, who welcomes Jack’s flirtation and to Miles’ dismay, she also happens to be a friend of Maya. One day, the four of them get together. Stephanie and Jack hit it off while Maya and Miles stay distant, or rather Miles stays distant. But this leads to a wonderful and delicate scene where Maya tells the depressed Miles how a bottle of wine is actually alive.
Virginia Madsen is indeed miraculous in this movie. There’s a rare level of beauty her Maya emits, in being able to understand and love a sour puss like Miles. The way her voice caresses Miles’ wounded heart. The way she gingerly lays her hand upon his after she talks. Maya is an irresistible home of comfort and wholesome love. She is the heart of the movie… while the penis is obviously Jack. Thomas Hayden Church’s performance is not limited to the archetype of the hilarious and cartoonish sidekick. His character is given a refreshing human weight. There is one scene where he breaks down and is at mercy of Miles’ help. Paul Giamatti as Miles delivers a frustrating act of a corked bottle waiting to erupt with a fizz. It’s a fine lead performance. Sandra Oh is also excellent in a supporting role and delivers a heart wrenching display of emotions with a motorcycle helmet.
I admire the director Alexander Payne for he keeps getting better and better. I loved “About Schmidt” where the most memorable scene is Jack Nicholson crying. Now, here’s “Sideways” where Virginia Madsen almost manages Paul Gimatti to crack a smile. I wouldn’t compare this movie to a great wine, because I am too much of a philistine to realize if a wine is great. I’m certain though that unlike alcohol, it’s one enlightening anti-depressant. So drop the bottle and play spin the DVD.