Sideways (2005): a movie review

I just saw the movie Sideways again last night and it renewed my love for the movie. This truly is one of my favorite movies. I love the friendship between Miles Raymond (Paul Giamatti) and Jack Lapate (Thomas Haden Church). They are complete opposites. Their personalities clash throughout the movie. But as the movie goes on, you come to see that this clash is necessary: they see in the other what they lack in themselves.



We meet Miles on the flip side of a sour divorce, a disillusioned 8th grade English teacher. He is obviously gifted with words and a gifted writer, but he is essentially a failed novelist, having yet to successfully publish his book. And his knowledge of wine is tremendous. Jack is a struggling actor (stuck being the voice in infomercials) and is looking forward to being married in a week. Back in college they were room-mates and they’ve been friends ever since.

As a gift to his friend Jack, Miles plans on taking him to the wine country in Santa Ynez Valley, in California, with beautiful countrysides, rolling hills full of grapevines. There they will enjoy the wine, play golf, enjoy nature, and give Jack a stylish transition from the single life to the married one. But there is a problem: Jack wants to have sex on his last week of freedom! Jack is hilarious. He is cocky and lets it all hang out, and when it clashes with Miles’ depression, negativity, and pessimism, I was laughing out loud.

When they’re at a restaurant, Jack sees Maya for the first time, a waitress, someone who Miles has had a secret attraction toward for a while. But Miles is still scarred from his divorce and he thinks she is married anyway. But thanks to Jack’s Sherlock Holmes-style detective skills, we find that she is divorced as well.

Maya is my favorite female lead in the history of the movies, barely beating out Grace Kelly in Hitchcock’s Rear Window (1954). Her voice is so soothing and she is so beautiful and understanding, and she is such a good listener. She knows exactly where Miles is coming from and always looks him straight in the eye. Her gaze isn’t a stare; it is so healing and sympathetic. She is so selfless and noble. I remember the scene where Miles trusts her enough to lend her the manuscript of his unfinished novel, not yet grammatically corrected. What is the magical thing that happens? She reads it. All of it. She understands it. “Did all of that really happen to you?”, she asks in a voiceover. “That must have been so painful.” Her voice is so genuine.

The most beautiful scene in the movie is when they are on her back porch and she asks Miles why he loves Pinot so much. He is nervous as we all are when we are called on to explain something that means so much to us, all the more so for Miles since Pinot, and his reasons for loving it, are bound up with his identity: he loves Pinot because the Pinot grape needs to be nurtured and coaxed into its fullest expression just as he himself does.

This is when Maya realizes Miles is talking about himself: when she falls in love with him. Maya gently launches into why she got into wine. This scene touches me to the very marrow: they're talking about wine, but they're talking about so much more. It makes you think about so much. It makes you think about what it would feel like to meet a woman who shares your interests and loves and in a way that she can illuminate a whole new dimension of it, and yet at the same time show forth her inner beauty. The scene is utterly transcendent. I adore it.

Then of course we meet Stephanie, Jack’s fling, and complications multiply. Jack’s wedding the following weekend has to be kept a secret. This, while Miles is really falling in love with Maya. So, there is real love, but the lurking deception threatens to ruin everything.

The movie is hilarious. I love it when Miles and Jack are meeting Stephanie and Maya on a double-date. Miles’ depression and negativity threaten to ruin Jack’s chances of sleeping with Stephanie, which leads to Jack warning Miles to be cool. Oh yes: “If they want to drink Merlot, we’re drinking Merlot.” “No!!”, Miles screams: “I’m not drinking any fucking Merlot!!” Hysterical.

Giamatti plays a schlub perfectly. The drama of the film belongs to his character and it is heartbreaking. I can’t think of actors that better portray that element of misery that is self-inflicted. Not only is Sideways one of the best buddy-movies there are, it’s a background-documentary on wine itself. The movie is full of wine trivia, interesting information on how to grow it, what factors are involved, how to criticize it, the insider’s peculiar way of drinking it: it’s almost a ritual. The movie as a whole is a masterpiece.