As Alexander Payne’s film opens, we meet Miles, a tired forty-something English teacher with an unpublished book, a failed marriage, and a keen taste for fine wine. It seems that Miles’ only strength is his interest in wine – his skill as a wine taster and his vast knowledge of the art of the grape. So in wine – and only fine wine – Miles finds his confidence, his refuge, and his escape. Wine country is Miles’ secret garden, and in honor of Jack’s impending nuptials, Miles is taking him on a special tour of this magical place.

With a couple boxes of his favorite bottles in the backseat, Miles heads to L.A. to fetch his college friend, Jack – once a daytime drama star, now doing television commercial voice-overs. Jack is a little bit anxious about getting married in a week, and ready for a little escapist fun. For this final week, Jack has only one thing in mind . . . enjoying good wine is not it. And he is not the least bit subtle about his agenda.

Since vacationing up in wine country would not be quite so acceptable if the excuse were one last bachelor fling, Jack announces to anyone who asks that the getaway is a celebration of the long-awaited publication of Miles’ book. Although Miles is never comfortable with this exaggeration, he is not strong enough to stand up to Jack and put a stop to the lie. Besides, the deception seems to work, and soon Miles and Jack are hitting it off with Maya and Stephanie. Once Jack and Stephanie head off to the wild side, Miles is left to fend for himself with Maya. By this point in the movie, we understand that Miles is in such a crisis of self-pity that there is no hope for their time together.

Poor Maya – she really does seem to like Miles, but he is so mired in the past and filled with self-doubt that he avoids every indication of her growing fondness for him. To him, it is a foregone conclusion that things can’t work out with Maya. After all, her interest in his book is sparked by a lie. It’s really too bad, because Miles sees that Maya is attractive, funny, and very up on her wines. She even asks if she can read Miles’ book.

Miles’ book, as he describes it, is a semi-autobiographical novel, so much about himself that he seems unsure if it should be called fiction. It is complicated beyond comprehension, and Miles doubts that anyone (especially potential publishers) has ever bothered to finish it. See, this manuscript is Miles’ life’s work. It is his life in a box. It has been twice rejected, and will most likely be rejected again. Miles’ identity and worth are bound up in those pages, and he has put them in Maya’s hands.

The most telling moment in the movie comes when Maya and Miles share their particular fascination with wine – his with Pinot Noir and hers with wine in general. Miles’ description of the Pinot Noir sounds like a self-portrait – all thin-skinned and overly sensitive. Maya’s perspective is one of hope, wonder, and possibility – wine is meant to be enjoyed, and opening a great bottle is a celebration. Miles has been so wrapped up in the complexity and nuance that it must never have occurred to him to actually enjoy the moment.

What a mess. If you’d asked me the day after I saw Sideways whether I’d recommend it, I would probable have said “no.” Jack’s self-absorbed behavior and nonchalant attitude were off-putting. Miles’ self-pity and cowardice were pathetic. If I hadn’t promised to write a little something about this movie, I would have long since dismissed it. If it had been a wine, I might have winced and moved on. The thing is that so many good things were said about this movie. I had to be missing something. And it turns out that I was. I’m glad I had to think about it.