Miles (Paul Giamatti) is a struggling writer who makes ends meet by teaching 8th grade English. Or he’s an 8th grade English teacher with pipe dreams of being a writer. I mean, when does your day job become your job-job? Take me, I got the video store and a newspaper I freelance for and this website, of course, but is that that for the long run? Am I ever gonna publish my novel or put actual effort in turning all my “great” movie ideas into screenplays and sell them? I’m only 24, so I can still coast for another 5-6 years, seeing where things take me. But once you go into your 30s, I imagine you start wondering whether your “life” hasn’t started yet or if your temporary occupation has become permanent.

Went a wee bit sideways there, sorry. So Miles is well into his 30s, divorced, depressed and “universally rejected”. The only thing that still brings him pleasure is his passion for wine and, as his best friend Jack (Thomas Haden Church) is about to get married, Miles takes him on a road trip through the California wine country. The plan is to eat good food, drink good wine and play golf for a week, but Jack also intends to get both of them laid in his last few days of bachelorhood, whether Miles wants to or not.

It took me a while to make up my mind about “Sideways”, for this isn’t a flashy get-your-thrills ride. The story starts slowly and only gets into gear an hour into the film. That’s not necessarily a bad thing. Right from the start, I was enjoying the nuances of Giamatti’s performance and the insightful dialogue. What I didn’t like so much was the oddly upbeat score and the unimaginative use of montage to illustrate the passage of time, which still felt slow anyway.

Fortunately, things pick up considerably once Jack and Miles hook up with Maya (Virginia Madsen) and Stephanie (Sandra Oh). Jack should feel guilty about cheating on his fiancée, but he goes into this affair with careless glee while it’s Miles who’s hesitant about being intimate with someone new, something he hasn’t done in years. Giamatti is increasingly affecting as Miles, who he aptly described in an interview as a “guy who’s cultivated this ersatz sophistication- I’m a writer! A wine expert!– but (is) just a failed writer and a drunk.”

The wine-tasting, which seems like a gimmick initially, provides metaphors integral to the film. A bottle of wine is like a life, constantly evolving and taking different flavors, but eventually it peaks and if you wait too long to open it, it might just turn to vinegar. Another thing that builds to wonderful effect is the complicity between the two male leads. Jack is practically Miles’s opposite, all pushy and flirty and superficial, but you can still see why they’re friends. Thomas Haden Church is a lot of fun and he plays well against Giamatti. They have some truly hilarious scenes in the second hour of the film where we can see how each has a tendency to get into embarrassing situations and needs the other to fix them.

As “Sideways” progressed to its near-perfect final scene, I found myself genuinely loving it. Not quite as much as the middle-aged critics who are calling it the best film of the year, but I guess I’m too young to fully appreciate some of the themes. Maybe I oughta ease up on the beer and give wine a try?

UPDATE (12/02)
Just watched the film again and, as I suspected, I liked it even more. The first hour didn’t feel slow this time, Payne’s direction seemed more cohesive and the story hit me more intensely emotionally. As for the things I already loved, such as the brilliant writing and acting, they also worked even better for me during this second watch. I still don’t think this is the best picture of 2004, but it’s right up there.