Great Character: Miles (“Sideways”)

Scott Myers
Go Into The Story
Published in
3 min readApr 27, 2012

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

Miles in the movie ‘Sideways’.

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 reflecting on why he’s so into pinot noir wine:

“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 and Taylor care about, not that Miles is sympathetic or likeable, but that’s he interesting.

Here is a quote from an interview with Alexander Payne on this very subject:

Appeal comes from truthful and complex characters. I hate when movie people say, “Your lead character has to be sympathetic,” which for them means “likeable”. I don’t give a shit about “liking” a character. I just want to be interested in him or her. You also have to make the distinction between liking the character as a person and liking a character as a character. I mean, I don’t know whether I like Alex in A Clockwork Orange or Michael Corleone in The Godfather as people, but I adore them as characters. Besides, “liking” is so subjective anyway. So many American movies of the eighties and early nineties bent over backwards to make the protagonist “likeable” in a completely fraudulent way, and I detested them.

I love Sideways 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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