In a recent NY Times article, A.O. Scott calls Sideways the most overrated film of the year. He allows it's "well written and flawlessly acted, funny and observant" but feels it doesn't quite live up to all the critical hype (i.e. having been named film of the year by critics' groups in LA, NY, SF, Chicago, Toronto, etc.). Even worse, says Scott, is that critics love the film (and other films like it) because the main character is a critic himself:
Still, the reaction to "Sideways" is worth noting, less because it isn't quite as good as everyone seems to be saying it is than because the near-unanimous praise of it reveals something about the psychology of critics, as distinct from our taste. Miles, the movie's hero, has been variously described as a drunk, a wine snob, a sad sack and a loser, but it has seldom been mentioned that he is also, by temperament if not by profession, a critic.
And furthermore that the film defends Miles' critical approach to life:
This makes him, among other things, an embodiment of the critical disposition, and one of the unusual things about "Sideways" is that, in the end, it defends this attitude rather than dismissing it. Yes, the film pokes fun at Miles's flights of oenophile rhetoric - all that business about asparagus and "nutty Edam cheese" - but it defies the usual Hollywood anti-intellectualism in acknowledging that, rather than diminishing the fun of drinking, approaching wine with a measure of knowledge and sophistication can enhance its pleasures. There is more to true appreciation than just knowing what you like.
I don't think Sideways defends the critical attitude at all...not any more than than it does Jack's hedonistic lifestyle. Neither character's life seemed any more fullfilling than the other's. You could argue that Miles seemed to grow as a person over the course of the film, indicating the triumph of the critic, but Jack didn't seem to want to grow that much. Jack knows he's got some issues, but being as self-aware as Miles, he's not only content to live within his boundries, but almost revels in it. And in the end, both characters find what they're looking for in a relationship. If the critical character wins in this movie, I didn't see it.