Teacher and unpublished novelist Miles (Paul Giamatti) takes his best friend Jack (Thomas Haden Church) on a trip to the wine country of California for to celebrate Jack’s last week of freedom before his wedding on Saturday. Miles is a wine connoiseur, and his plan is for them to eat good food, play some golf, and sample the finest wines the vineyards’ have to offer. Jack, a rogueish C-list actor, has a simpler and less sophisticated goal: to have a last fling before tying the knot. And he wants to make sure that Miles gets some, too.

This basic set-up could serve as the plot for a brash and farcical buddy movie, but Sideways emphasizes the drama over the comedy. Miles is badly depressed over his marriage that broke up two years ago, and over his chances of ever selling his novel, and he drinks too much. Jack manages to hook the two of them up on a double date, and while Jack practically hops straight into bed with Stephanie (Sandra Oh), shy Miles struggles to find the right things to say to fellow wine lover Maya (Virginia Madsen).

In a meandering series of events, the week plays out with Miles getting ever more frustrated with his inability to progress his infatuation with Maya, and ever more infuriated with Jack’s shameless infidelity. There are a few big laughs, but most of the humour is softly sarcastic, with a touch of bitterness. It’s not a fast-moving story, and in places the film does feel slow and over-extended. But like a fine wine, it’s meant to be savoured and appreciated for its many nuances and flavours rather than downed in a single Hollywood gulp.