Sideways was the 2004 award contender about a pretentious writer-in-the-making who takes his C-list actor friend to Santa Barbara wine country on a week-long bachelor party. Miles, the writer, is still reeling from his divorce two years earlier. Jack, the actor, is an irrepressible horndog looking for more action before marriage. They wind up spending time with Maya and Stephanie, two wine aficionados who we're meant to understand deserve way better than these guys. Insight, snobbery, and occasional hilarity ensue.
In just about every significant way, I was not the same person a decade-and-a-half ago, when I first saw this movie in the run-up to the Oscars. And that person didn't like this movie much at all. It had a few memorable one-liners (including, notably, one that apparently destroyed real-life sales of Merlot for years and years). But none of the subject matter felt familiar to me, and it wasn't a movie trying to draw you in at all -- it wanted you at arm's length from its major characters.
Now, much has changed to make me more receptive to Sideways. I'm roughly the age of the characters in the film. I've developed some modest appreciation for wine (and have even been to wine country myself -- twice). Sideways is still in many ways unlikable, but to me it is now in many more ways understandable.
What I think I appreciated the first time, and certainly appreciate now, is just how good the acting in the movie is. Thomas Haden Church (as Jack) and Virginia Madsen (as Maya) were both up for Supporting Role Oscars here, and deservedly so. It's a bit of a cliche when you know you're hearing the One Speech a character has that is the movie's "hand extended for an Oscar" moment, but they both get it and they both nail it -- Church for Jack's complete emotional meltdown, Madsen for her quiet and introspective monologue about what wine means to Maya. Sandra Oh is solid too; this is far from her first role, though this may have been the turning point where more people would begin to recognize her.
But Paul Giamatti dominates this film. And while other awards like the Screen Actors Guild, the Golden Globes, and the Independent Spirit Awards did have him as a nominee, the Oscars leaving him out feels like a pretty egregious snub. Giamatti is so natural as this character that I suppose it's easy to overlook the tightrope he's walking: Miles is sympathetic but also unlikable, a victim of circumstances but a misanthrope of his own making, a walking contradiction. He's sweet in one scene, horrible in the next, and quite interesting throughout.
The acting is the draw here, though. The plot of Sideways is rather thin and very low stakes; it's a bit of a wonder to me that the one Oscar it did win was for Best Adapted Screenplay. Even though I like it now, quite a lot more, it would still be a stretch to call it an essential movie that "you have to see." But I would call it a B+. If you're into quiet little movies driven by dialogue and character, you're likely to be a fan.
Does this mean I'm now going to be looking out for more movies I once disliked to give them another chance? No, not really. There's too much new out there to see, or too much to revisit that I know I loved. But something about Sideways was speaking to me, telling me I should give it another chance -- and I'm glad I did. Perhaps another case like that will come along at some point.
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