Put simply, Sideways is one of the best, most entertaining dramedies I have ever seen. It manages to pull off the difficult task of making its characters both absurd and sympathetic at the same time. And not only that, but I feel like I learned some things about the intricacies of wine to boot.
Sideways is the story of struggling writer Miles Raymond (Paul Giamatti), who is taking his best friend, struggling actor Jack (Thomas Haden Church), on a weeklong tour of the California wine country so that they can let loose before Jack's impending wedding the next Saturday. Miles and Jack view the trip differently: Miles sees it as an opportunity to escape his life for a week and sample some fine wines, eat some good food, and play a little golf, while Jack wants to get drunk, get laid and also get Miles laid, during this last week of "freedom."
The two of them end up meeting Maya (Virginia Madsen), a waitress at a local restaurant, and Stephanie (Sandra Oh), a wine pourer at one of the vineyards. Jack is insistent to Miles that Maya is interested in him, but Miles, still depressed from a divorce two years prior, is reluctant to give in, afraid of being hurt again. Meanwhile, Jack and Stephanie hit it off, and Jack thinks he's falling in love with her -- but wait! -- he's getting married on Saturday and Stephanie doesn't know this.
So we follow these characters as Miles attempts to come to terms with an unpublished novel and a case of alcoholism -- that doesn't seem to him like alcoholism because he's only drinking and analyzing fine wines, but it's alcoholism nonetheless -- and Jack attempts to figure out what he really wants to do with his life.
Now, the way I have described Sideways does not make it sound like a comedy, but rest assured, with Alexander Payne at the helm, this film is filled with big, big laughs, mostly brought about by the brilliant performance of Thomas Haden Church (who received an Oscar nomination). He infuses Jack with such gusto and false sincerity that you get the feeling that with that smile, he could disarm any woman he wanted to. Jack really cares about Miles, who is also mostly just concerned with himself, but Jack wants him to quit moping around and be happy again.
Paul Giamatti also gives a wonderfully nuanced performance and really anchors the film; we want Miles to succeed, but we often find ourselves shaking our heads in disbelief at his actions. Giamatti plays the part perfectly, and is truly one of the more underappreciated actors working today (as evidenced by the Academy's snub of this performance).
While they're tasting wine, Miles goes through a long process to determine if it's a good wine or not, but you wonder if he's actually even enjoying it. Jack, on the other hand, mostly only comments, "It tastes pretty good to me." Yeah, that sounds about right.
March 5, 2005