Miles (Paul Giamatti) is a depressed wine lover who is struggling to get past his divorce, even after two years. Jack (Thomas Hayden Church) is an actor who never really made it, and is about to get married. Miles takes Jack on a wine-tasting week away expecting lots of drinking and golf, but Jack is more keen on getting laid – and getting Miles laid. Then there are the ladies that they meet – but I don’t feel like mentioning them given that the only role they have is to be sex objects and to be treated poorly.
I don’t get this film. I don’t really understand why it was so highly lauded. Perhaps it is that we don’t see a lot of films of middle-aged men having breakdowns. Do we? I just found it boring, both the men had appalling attitudes toward woman and towards life in general. There were several scenes that seemed totally implausible, and really, just annoyed me.
Sideways won an Oscar for Best Writing, Adapted Screenplay and was nominated for Picture of the Year, Best Performance by an Actor in a Supporting Role (Thomas Hayden Church), Best Performance by an Actress in a Supporting Role (Virginia Madsen), and Best Achievement in Directing (Alexander Payne).