Great Character: Miles (“Sideways”)

April 27th, 2012 by

Protagonists must be sympathetic. They have to be likeable. We need to root for them. That’s straight out of Screenwriting 101, right?

Uh, no. Protagonists can be deeply flawed individuals who are drunks, live in complete denial of their psychological issues, act superior to others, and even steal money from their own mother… just like Miles does in the 2004 movie Sideways (screenplay by Alexander Payne & Jim Taylor, based on a book by Rex Pickett).

The movie’s story synopsis per IMBD:

Miles is a failed writer living a meager existence in San Diego as an English teacher. With his career seemingly fading and the fate of a book hinging on a publisher’s decision, Miles is depressed with himself and what he hasn’t achieved. Jack is a television actor whom some recognize but not many do, as if he were a minor actor who got a taste of success. With his best friend Miles, the two embark on a road trip through California’s wine country. Miles wants to give his friend a nice sendoff before married life, while Jack simply wants to have a fling beforehand. As they’re both nearing middle age with not much to show for it, the two will explore the vineyards while ultimately searching for their identities.

And on that trip through the wine country, Miles has moments like this:

And this:

And how about this monologue from Miles:

“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 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 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.”

Miles is such a narcissist, even when he talks about wine… he’s talking about himself!

But you know what? He’s one of the most interesting movie characters in the last decade, and whether you grow to understand him or not, he is compelling. And that’s all that Payne & Taylor care about, not that Miles is sympathetic or likeable, but that’s he interesting.

I love this movie for a lot of reasons, one of which is because the Protagonist is cut from such a different cloth than most mainstream films.

And that’s in part why Miles is a great character.

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4 thoughts on “Great Character: Miles (“Sideways”)

  1. Couldn’t agree more. I love this film, and Pinot Noir!

    The scene at Miles’ mother always confused me a bit, though. The whole thing seems like a set-up to show Miles stealing the money and I can’t really figure out why that scene is there. Or why it’s so to the point, rather. Is Miles acting so callous towards his mother telling us something about his background and showing how jaded and selfish he has become?

    Now, the opposite would have been death. Miles stopping by his mother’s to show his love so we get the feeling that he’s a good guy after all and we can root for him. Yuk.

    But it’s almost like the filmmakers are rubbing it in that he’s unlikeable – an anti “Save The Cat” moment, if you will.

    Any thoughts on this?

  2. What I gathered from that scene is that rather than he go through the trouble of asking her for the money and having to have a discussion about it, he just takes it. She did ask him at the end of that scene (if this is the scene we are talking about), if he needed any money.

    I think Miles is very cut to the chase in that way. Jack is the same I think, but on a more mellow level.

  3. Thank you for nailing this. I will bookmark and save so that I can use it every time I hear the first few sentences uttered.

  4. […] Although they did not let attendees keep the wine glasses, trade tasting at Pinot Days this year was a delicate and full-bodied wine festival because I love Pinor Noir like Miles. […]

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