This is a movie I’ve been tempted to watch many times since it was released five years ago. I’d see it in the comedy section of Blockbuster, calling to me. And yet, I would always walk away, saying, “Maybe another day”. Tonight, my parents finally convinced me to sit down and watch the movie. And I found myself surprised by the characters, by the tone in general. But in a good way.

Miles (Paul Giamatti) is a divorced high school English teacher waiting to hear if his book will be published. His friend Jack (Thomas Haden Church), a D-list actor, is getting married in a week. Miles loves Napa Valley and takes Jack along for a week of golf, good food and good wine. Jack has other plans. Jack decides they are both getting laid. Along comes Maya (Virginia Madsen) for Miles and Stephanie (Sandra Oh) for Jack.

After rereading the last paragraph, the synopsis could almost belong to a Judd Apatow-style film, right down to the numerous f-bombs and copious amounts of nudity (and yes, there is a good amount of nudity, just a warning). But Sideways feels less like a “buddy comedy” and more like how this kind of situation would unfold in the real world. Writers Rex Pickett and Alexander Payne have created characters that are flawed, but not necessarily terrible people.

Haden Church does a really great job with Jack, walking the line between guy you like and guy you despise. Even when he does something pretty despicable (like cheating on his fiancé), you hate what he’s doing, but you don’t hate him. It works because Jack just can’t comprehend that what he is doing is really wrong.

While Miles is the protagonist, he is far from a hero. In many ways, he is liar, a petty thief and a coward. But unlike Jack, Miles is completely aware of his flaws and hates himself for it. He is a man that is well aware of his failures, both professional and personal, and just doesn’t know how to change. Giamatti makes the character relatable, but by no means perfect.

One of the very best performances, however, is by Madsen as Maya. She plays the character with intelligence and a certain inner grace. She sees more in Miles than he sees in himself and most of the growth of their relationship is shown through the silent moments of the two together. I attribute much of that from Madsen’s performance. I could also appreciate that Madsen looks like a real woman (one with curves). Sandra Oh works well in her role as a semi-bohemian free –spirited single mom, but you connect much more with Maya than you do with Stephanie (and I think the writers meant for it to be that way).

And behind the relationships, successes and failures is the underlining theme of wine. Three of the four main characters have a real passion for the drink and Maya and Miles in particular have some beautiful monologues about why they love it. The great thing is that they slowly stop describing wine and start describing themselves, but they don’t necessarily realize it. Wine becomes a symbol of how beautiful their lives could be if they could only grow it just the right way.

OVERALL: Slow to start, but you can’t help but care about these characters, flaws and all.

4 out of 5 stars.