Ok, I know it’s not cool to dig too far back into the past of popular culture. After all, it’s not popular culture if it’s not up-to-date, right? But a conversation this evening prompted me to reopen the case of the 2004 film Sideways.

Yes, yes, I know, it’s four years old, ancient history by pop-culture standards. But nonetheless there are some important lessons to be learned from this film. Please don’t read on if you have not seen it. What follows would only ruin the film for you – and you really don’t want that, trust me.

I am assuming that if you are still reading this, you have already seen the film. So you know that Paul Giamatti plays a man who spends his life running away from relationships, and somehow convinces himself that what he actually cares about in life is “wine tasting”.

I’m going to cut to the chase here. The single most important moment of this film is the point where Giamatti’s character sneaks up to his mother’s bedroom and steals her well-hidden stash of cash. Presumably this establishes him as a morally worthless (and therefore uninteresting) character. I know that this moment disturbed quite a few people.

But wait! There is more here than meets the eye. Why does his mother keep cash where he can find it and steal it? Isn’t it because she wants him to steal the money from him? I would argue that, at its core, this film is actually painting a portrait of a mother/son relationship that is so extremely disfunctional that the mother actually wants her son to take moral shortcuts that betray his core principles – so that he will remain emotionally dependent upon her.

We eventually see, in the main character’s interaction with his ex-wife, that he has unwittingly sabotaged that relationship – because he cannot see his former spouse as an equal, but only as an all-powerful mother figure. By the end of the film, when our hero has found a good woman and is trying to begin again, we are not told whether he lives happily ever after, or falls back on his old self-destructive ways. My guess is that the prognosis is not good.

So what we have here, in the guise of a frothy comedy, is a deeply gothic psychological melodrama, coming at us sideways. I would be curious to know whether people agree with my analysis.

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