So the best approach is to toss out either your intense desire to love Sideways or, alternately, your stubborn desire to hate it, and just watch the damn thing. What got lost in the hype is that this is one of those unassuming, mostly wonderful movies stocked with tiny pleasures, hitting a few peaks where it's even sublime, and flawed in ways that are more charming than annoying. It's hard to tell whether it's primarily a buddy-dramedy or a wine-country tourism video, or vice-versa, but it's hard to fault a movie that so effusively encourages you to drink lots of good wine. I wish I could say the same for my fucking Nazi of an AA sponsor.
Few ensemble casts in recent memory have been as simultaneously repuslive and sexy as this one; with the exception of Virigina Madsen, who is always easy on the eyes, you get Paul Giamatti, Thomas Haden Church, and the beguiling succubus Sandra Oh, whom you can't take your eyes off even though she seems somehow like she is about to stab you in the eyeball at any moment.
The characters are as fertile as wine-country soil (I suspect that was terrible writing, but I'll let it stand, or "stet," as my fucking Neo-Nazi of an editor would say), as we meet all four leads a little ways down the point at which their lives peaked, so they're all a little used, a little beaten, a little resigned. The tension comes from the promise of renewed hope, and fortunately the film doesn't go the standard route of making us all feel better about our increasingly disappointing lives. So there is some insight here that you'll never find in, like, a typical Tom Hanks-Meg Ryan cute-fest.
Giamatti is Miles, a drunkard semi-to-mostly-failed writer still reeling from a bitter divorce long past the point where it is socially appropriate; he's taking best-friend Jack (Thomas Haden Church), an actor of increasingly marginal fame (good casting) on a wine-country road trip in lieu of a bachelor party for Jack's pending nuptuals. Along the way, the buddies run into Stephanie (Oh) and Maya (Madsen) and bond over incredible volumes of wine and a general, tacit acknowledgement of each other's desperation.
It's brilliantly acted, no doubt about that. Each actor brings a different kind of emotional weight to the proceedings, and provides subtle and surprising moments of real revelation. I wasn't terribly impressed with the script, which had a couple too many contrivances to get our heroes into trouble, and a few too many lines that may as well have been accompanied by bright flashing neon red subtitles that said "LISTEN CAREFULLY! HERE'S THE MEANING OF THE MOVIE!" In particular, a scene in which Miles explains what he likes about Pinot Noir could not be more obviously telegraphed, and while Giamatti is incapable of delivering a line dishonestly, it's unfortunate that the dialogue was so preciously crafted in a few spots.
Still, there is, as Jar-Jar Binks would say, "muy muy" to like about Sideways it delivers a pang of confessional truth most folks can't access until they've got three bottles of wine in 'em. Plus, I commend any film that outright endorses drinking and driving.