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Sideways, 2004

Miles (Paul Giamatti) goes on a road trip with old college friend Jack (Thomas Haden Church) a week before Jack is set to get married. Grappling with disappointment over his own unsuccessful marriage and inability to get his book published, Miles is finally convinced by Jack to take a chance on a woman he's admired from afar, a wine-savvy waitress named Maya (Virginia Madsen). But Jack has plans of his own for the trip, and the friendship between Miles and Jack begins to fray a bit.

I can see why this film is so popular. The performances are all terrifically entertaining and the chemistry between the actors is great. While I found the character of Jack not nearly as charming as I think he's meant to be---and honestly kind of tiresome at points--Church keeps him just engaging enough and the script pokes just enough fun at him to keep things on the right side.

I really appreciated the film's take on the complications of romantic relationships. In a more simplistic film, Miles would have to learn all about cutting loose. But the reality is that Jack's hedonistic, selfish approach to life is hurtful to others. Likewise, the withdrawn and pessimistic approach that Miles takes isn't getting him anywhere. For most of the film Miles is on a see-saw between his angry introvert ways and following Jack's more brash, self-serving methods. It's about Miles finding a way to move past his resentments and being open to new possibilities.

The setting in wine country is a fun one. Yes, of course it gives us plenty of opportunities to watch Miles pretentiously instruct Jack on the art of wine tasting. But the way that Miles approaches wine---already armed with a degree of irritation--speaks to the way that he is approaching everything in his life. He is not able to appreciate simple joys because he is so bound up in himself.

Madsen is nicely understated as love interest Maya. She has enough dimension to her so that she doesn't just feel like a plot device. Sandra Oh makes a great impression as the free-spirited Stephanie, a woman Jack woos while conveniently omitting the details of his upcoming nuptials.

I didn't have any specific negatives for this film. I get the impression that Jack was meant to be taken as more of a lovable rogue, especially in the beginning, but I thought that his schtick got a bit old at times. I totally understand that his bravado is his own response to the anxiety he feels about the upcoming wedding, but there were a lot of times that the way a scene was shot/scored seemed to imply that what was happening was fun and quirky. It might be an accurate-ish portrait of a version of a mid-life crisis . . . but there's a reason I don't spend time around middle aged men having a mid-life crisis.

Again, I can totally understand why this film got so much praise when it came out. It's held up well, and it's an easy, breezy way to spend 100 minutes.