I’m terrible at keeping up with movies, so when I hear that Sideways is nominated for an Oscar, it goes in one ear and out the other. When I hear that it’s funny and painful and all that, I just file it away under “things I should see one of these days.” When I hear that it’s got Thomas Haden Church and Sandra Oh, two of my favorite underappreciated actors, my ears prick up a bit. When I hear that it’s directed and co-written by Alexander Payne, well, that’s just too much: I have to go see it.

Payne was behind Citizen Ruth and Election, two wickedly acerbic comedies featuring miserable, blinkered losers that you couldn’t help but love a little. Sideways’s Miles (Paul Giamatti) is a sad sack in the same vein as Ruth Stoops and Mr. McAllister, but this time around, Payne doesn’t leave you on the outside of the character looking in. Rather, you sink into his droopy, ringed eyes and are trapped inside of them. You feel all of Miles’s desperation, the walls closing in around him, even as you want more than anything to smack him upside the head and tell him to snap out of it.

Luckily, the film isn’t just two hours of Miles moping around (although there is plenty of that), and Jack (Church) is there to provide a foil for him — not that he doesn’t have his own bundle of issues to work out, or avoid working out. Maya (Virginia Madsen) and Stephanie (Oh), on the other hand, actually have their act together, more or less; they’re not necessarily content, but they don’t seem to be in living out pre-mid-life crises like Miles and Jack. Over many, many bottles of product-placed wine, these four mis-connect, connect, disconnect, and reconnect.

In his commentary on the Election DVD, Payne made that movie sound like a love letter to his prosaic home town of Omaha. The way he films them, the small towns of California’s wine country might as well be in the Plains themselves, with their generic architecture, restaurants, and car lots. Draining the romance out of the typically idealized wine region (images of winemaking involve migrant workers, bottling machines, and tanker trucks) not only reinforces Miles’s dissociation but prevents the viewer from being distracted by scenery, keeping the focus on the characters: the actors and the pinots and cabernets they express themselves with. It still makes me really want a drink, though.