Do not drink too much. Do you hear me? I don't want you passing out or going to the dark side. No going to the dark side!

                             -- Jack Cole, Sideways (2004)

In the film Sideways, Paul Giamatti plays Miles Raymond, a forty-something unsuccessful writer, wine-aficionado, and  depressed middle school English teacher living in San Diego, who takes his soon-to-be-married actor friend and college roommate, Jack Cole (Thomas Haden Church), on a road trip through Santa Ynez Valley wine country. Miles wants to relax and live well. However, Jack wants one last sexual fling; at least that is their expressed agendas for the trip.

The agenda beneath the surface, however, has something to do with that male ritual of the mid-life crisis during a road trip. There are few thematic vehicles in the movie as hackney as this one, and Sideways is remarkable if only because it is able to rise above the well-worn material.  In a sense, the film is able to demonstrate why so many films (i.e. the (male) writers and film-makers) keep returning to it.  

Peter Rainer in New York Magazine writes [emphasis mine]:

Miles and Jack knock about as if they were still late-stage adolescents. They’re still figuring out who they want to be, which gives their strenuous efforts at happiness an added poignancy (and absurdity). We can see that Miles, who according to Jack has been “officially depressed for, like, two years,” is more than just a glum zhlub; he may not be able to get his book sold, but his love of language is as real as his love of the grape. When he talks about literature or his favorite wines, he isn’t showing off. He’s trying to live up to his own best image of himself, and he seems transported. In his own dim way, Jack understands this, which is why their friendship is more complicated than it appears. Jack is always telling the people they meet that Miles’s book is being published, and he isn’t being cruel—he’s trying to inspire Miles to be the guy he was before the two-year tailspin (and also get him some action).

There is a kind of conventional standard that adolescence is a time to figure who one wants to be, as if our sense of self was a collection of choices from a laundry list of potential facets of a persona.  Things have changed some, and those in their twenties and even their thirties can say they are figuring out who they want to be without getting a puzzled or disapproving look.  But speaking from experience, by the time one reaches the forties, the expectations are that one has all this stuff figured out.

For a 19-year-old like Dzhokhar Tsarnaev, the frustration and internal agitation comes from being frustrated in his attempts to get it figured in the first place.  For the forty-something like Miles, it was having believed once that one had it figured out, only to discover that either it has been lost or, worse, one never had figured out. Rainer continues:

Giamatti is letting us know that Miles’s eloquence about wine may just be a fancy way of tarting up his drinking habit, his sadness. But he isn’t simply replaying his Harvey Pekar from American Splendor—this is a whole other species of depresso: tender, enraged, rueful about what he has lost. At least Pekar was published.

The character of Miles I believe was raised in a similar fashion as I was: the only real expectation is that one be all you can be, to reach your potential.  In one sense, this approach to life is all fine and dandy, except there is no guarantee one's own understanding of that potential is going to be grounded in reality, or that reality is going to cooperate with achieving that understood potential.  In fact, life may just very well being actively resistant to such an achievement.

Becoming sensitive to not achieving this vision of a potential self can lead one to be the tender, enraged and rueful depresso.  It can also lead to a feeling of humiliation - that dark side.

(I tried to find a review of Sideways that specifically used the term humiliation and was unable.  It is as if the stating this particular facet out loud is too discomforting,  a train wreck we can't bring ourselves to look at.  Sadness and rage we can deal with, but not humiliation.)

I find Rainer's juxtaposition of tender with enraged intriguing.  Rage is not the first description of Miles Raymond that comes to mind, but it is a credit to Giamatti that he is able to authentically capture that rage which comes from a sense of being humiliation by life.  Or is it a rage against one's own self, that all the humiliation is not only of one's own doing, but well-deserved, some kind of justice being served by universe?

Possibly the thing that separates a Miles Raymond and a William Foster who goes on a violent rampage is that impulse to turn the blame for the humiliation on one's self. 

I am reminded of an essay that I had torn out from a weekly supplement and carried around for a number of years.  In one of the essay's threads, the author discussed the use of humor to cope with misfortune, starting with his upbringing in a Jewish  household. Later in life, he heard someone tell a joke in Ireland that was basically the same joke he had heard around the dinner table, except the characters were Irish and not Jewish.

The Irish version starts with a man, we'll call him Liam, in Church praying to God, or rather complaining.  "God," Liam says, "I don't understand.  I do everything I can to be a good servant to you and to follow the path you want us all to take.  I work hard everyday, I don't drink or smoke, I don't cheat on my wife, I am a good father to my children, I come to Church every week, I do my confessions.  And I don't have two shillings to rub together.  Yet my brother Seamus, he spends all his days drinking and smoking, he never comes to Church, he uses your name in vain, he cheats on his wife and mistreats his kids, and yet, and yet he is incredibly wealthy.  No matter what he does, he becomes wealthier and wealthier.  Why Lord, why?!" 

There is a great thundering in the air and suddenly a giant fist comes crashing through the roof of the Church and pins Liam against the pew, and a deep booming voice says "Because I fuckin hate ya, that's why."

Trying to make sense of the failure that is not reaching one's perceived potential (including trying to decide who is to blame) is probably a task we all must face, yet we rarely engage in a discussion about how it is we understand that potential, the dynamics and forces involved.  Usually we are left with grasping for some metaphor, some analogy that approaches some truth about it. Miles, in his effort to explain to Maya why it is he is so passionate about Pinot, says [emphasis mine]:

Uh, I don't know, I don't know. Um, it's a hard grape to grow, as you know. Right? It's uh, it's thin-skinned, temperamental, ripens early. It's, you know, it's not a survivor like Cabernet, which can just grow anywhere and uh, thrive even when it's neglected. No, Pinot needs constant care and attention. You know? And in fact it can only grow in these really specific, little, tucked away corners of the world. And, and only the most patient and nurturing of growers can do it, really. Only somebody who really takes the time to understand Pinot's potential can then coax it into its fullest expression. Then, I mean, oh its flavors, they're just the most haunting and brilliant and thrilling and subtle and... ancient on the planet.

Don't we all, to some degree, like to believe that deep down there is something in us haunting and brilliant, thrilling and subtle, there waiting to be expressed if only there was someone or something that will coax it to the surface. Someday my prince will come....