I watched “Sideways” at least three times before I decided I liked it. The characters are smug, entitled, loutish, pretentious and depressing, and yet like a good bottle of wine it required a delicate aging until I savored it for its maturity, beauty and perfection.

Miles (Paul Giamatti) is the Pinot Noir of pricks, a rare survivor of someone who’s likeable, clever and dopey all at once. Divorced for two years and scraping to find a publisher for the lengthy novel he keeps in not one but two shoe boxes, he goes on a trip to wine country for his best friend Jack’s (Thomas Haden Church) bachelor party.

Miles listens patiently as Jack announces his plans to get laid one last time before a life of marriage. Because he’s only tacitly unsupportive, we get the feeling we shouldn’t feel pity for either of them. Miles is in such a rut and yet still notoriously sarcastic, pitiful and righteous in everything he does we hope he might act up if he just gets laid too.

Alexander Payne’s film is darkly funny in this way, overwrought and pretentious at times but sincere and touching in a way we wouldn’t expect.

“Sideways” is a wonderfully well-crafted love story and coming of age drama for a group of middle aged men little seen in the movies. Miles and Jack’s courtships with the locals Maya (Virginia Madsen) and Stephanie (Sandra Oh) are lovingly relatable.

In one instant Miles can give a crash course on snobbish wine tasting, systematically examining its smell and its color before hilariously berating Jack for chewing gum. But contrast that with his and Maya’s theories on when a bottle of wine is at its best: even drunk they are mature adults capable of generating thoughtful metaphors on how drinking reflects mortality and the possibility of missing out on life’s luster and flavor if you don’t enjoy it at its peak.

“Sideways” matches its characters’ level of pretension with a trendy window panel montage and a jazzy soundtrack. It stays distant from these people and their tendency to embarrass themselves, and in the process finds pitch perfect comedy in some wonderful set pieces on the side of a hill, on a golf course and in the house of a local couple having sex.

This is a terrifically heart wrenching, intelligent and sincere film with a great ending that doesn’t last a second too long. Its tricky characters may be an acquired taste, but my pallet has developed the maturity to appreciate their charms.

4 stars


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