‘Sideways,’ a comedy-drama soaked in wine, turns 20

Alexander Payne’s film put Paul Giamatti and Thomas Hayden Church in wine country, where hijinks and heartbreak ensued.

Alexander Payne’s Sideways is a movie that I didn’t quite understand when I first saw it at 26, but it makes a little bit more sense when I see it again at 46. No, my life circumstances don’t quite match those of any of the characters, and I still have no real palette for wine. 

But I see how Sideways is a movie about men never really growing up. I don’t remember which critic said it back in 2004, but Sideways is essentially a teen sex comedy in which the “teens” are a couple of 40-year-old men. 

Those men of perpetually arrested development were middle-aged best friends Miles (Paul Giamatti) and Jack (Thomas Haden Church). 

Miles is a high school English teacher who is a failed novelist, like nearly all such teachers in the movies and considers himself a “wine connoisseur” when he’s really more of a depressed alcoholic coming off a divorce. Jack is a washed-up actor, about to marry but not quite ready to give up on sexual promiscuity. 

The two head off to Santa Barbara County for a two-man bachelor party, where Miles wants them to “drink some good wine” and “eat some good food,” while Jack’s priority is to get his friend laid, and implicitly get laid himself. 

The two spend much of their week in wine country with friends Maya (Virginia Madsen) and Stephanie (Sandra Oh), both developing feelings for their female counterparts. This leads to predictable drama, and while it doesn’t end triumphantly, Miles is paid the ultimate compliment in the end: He finds out that the woman he likes was impressed with his unpublished novel. 

Sideways, directed by Payne and co-written by the director and his usual partner Jim Taylor, has much to admire about it. It’s an impressive travelogue of Santa Barbara wine country. It’s often funny, while also having a point to make about the silly mistakes men make, even in middle age.