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Sideways (2004) Review

Sideways (2004) Review

TL;DR: Sideways (2004) rates 9 out of 10 on the rewatch scale. Two middle-aged men drive north for a week of wine tasting before one of them gets married, and both of them are worse people than the film initially lets on. It won the Adapted Screenplay Oscar and measurably damaged the American merlot market.
Sideways (2004)
9/10

Miles is a failed novelist teaching eighth grade English and waiting on a publisher who’s not going to call. Jack is an actor doing voiceover work who’s getting married on Saturday and intends to sleep with somebody first.

The 9 is for a comedy that keeps revealing worse information about its protagonists and never stops being funny. Miles is a self-pitying thief who steals from his mother in the first act, and the film knows it.

The withheld point is Jack, who’s written slightly broader than the other three and occasionally becomes a plot generator instead of a person. Thomas Haden Church is so good that it mostly doesn’t matter.

What strikes me about Sideways is how little it flatters Miles. Most films would ask me to pity a guy like this, and this one lets me watch him steal from his mother and keep laughing anyway. It’s sad and mean-eyed and very funny, and I’m happy to forgive its one weak spot.

The First Act Is a Trap

For twenty minutes the film appears to be about a decent man with a boorish friend. Miles knows about wine, quotes poetry, is grieving a divorce, and is stuck with a groom who wants a week of infidelity.

Then he visits his mother for her birthday, and while she’s out of the room he takes money from her dresser. It’s done quickly, without comment, and the film moves on.

Everything after that scene reads differently. His wine expertise is a way of being superior in rooms where he has no other standing.

His grief is a performance he’s been running for two years. The novel isn’t being rejected because publishing is cruel, and by the end he knows it. I think that dresser scene is the best single choice in the film, and it takes about six seconds.

That’s the film’s method throughout. It gives you a reading, lets you settle into it, then supplies one fact that reorganizes everything, and it never announces that it’s done so.

Paul Giamatti wasn’t nominated, and that omission was dead wrong. It was the loudest snub of that awards year. The performance is built entirely on suppression, a man who has decided he’s owed something and can’t say so, and awards bodies have never known what to do with a lead who refuses to have a big scene.

For Writers

A single unremarked action can recharacterize a protagonist more efficiently than any amount of interiority. The reader revises backward. That’s work they do themselves and therefore believe. Place it early and give it no weight. If the film had scored the moment or cut to a reaction, it would have been a scene about Miles being a thief. Unscored and unremarked, it’s information. The test for whether it worked: can the reader still like him? Sideways wants you to keep watching Miles with affection while knowing exactly what he is. That’s much harder to write than a simple fall.

Everybody Is Lying About Something

Jack doesn’t tell Stephanie he’s getting married. Miles doesn’t tell Maya that Jack is getting married. That makes him complicit. Stephanie finds out and breaks Jack’s nose with a motorcycle helmet.

The structure is a farce built out of one withheld fact, and the film plays the consequences straight. Maya is furious in a way that’s entirely proportionate and she leaves, and the film lets Miles sit in that for a long time.

Virginia Madsen has the film’s best scene and it’s a monologue about why she likes wine, delivered on a porch. That’s really about being thirty-something and alone and hoping something improves with age. Madsen was nominated and didn’t win, and it’s the moment people remember.

What makes the scene work is that Miles answers it badly. She’s said something true and vulnerable and he responds with more technical information, because talking about wine is the only way he knows to be in a room. The film cuts on his failure and doesn’t underline it. Madsen’s porch speech is my favorite scene in the film, and Miles fumbling his answer is the most painful moment in it. I wanted to reach through the screen and shake him. Sandra Oh’s Stephanie is the one nobody defends and she’s right about everything. She’s a daughter, she’s been lied to for a week, and her violence is the only honest reaction anybody has in the film. The film is aware of what it’s doing to its women. Maya and Stephanie both exist inside a week that two men have arranged around themselves, and the picture gives each of them one scene where the arrangement is visible from their side. That’s not equal weight and it’s more than the genre usually manages.

The Wine Is Character, Not Set Dressing

Everything Miles says about wine is about himself and the film trusts you to notice without a single line pointing at it. His contempt for merlot is snobbery with no basis he can articulate. His devotion to pinot noir comes with a speech about how it’s thin-skinned, difficult, needs constant attention and only expresses itself under exactly the right conditions. That’s a self-portrait he doesn’t know he’s painting.

The 1961 Cheval Blanc is the payoff and it’s the best joke in the film. He’s been saving it for a special occasion, and the wine is a Bordeaux blend heavy in merlot, the thing he claims to despise. He drinks it alone from a paper cup in a fast food restaurant.

That ending is precise. He doesn’t have a revelation, he doesn’t make a speech, he drinks the best thing he owns in the worst possible circumstances because he’s finally worked out that waiting for the occasion is how you end up with nothing. The paper cup gets me. I laughed and felt sorry for him in the same second, and I can’t think of a better last word on a snob.

For Writers

Let a character’s expertise be a confession. What somebody chooses to be knowledgeable about, and how they deploy it, characterizes them faster than any biography. Never explain the parallel. The pinot speech works because nobody in the scene says it’s about him, and the audience makes the connection and owns it. Then subvert the expertise once. The Cheval Blanc reveal costs the film nothing and demolishes two hours of Miles’s authority in a single fact he already knew and never applied to himself.

Payne Films Middle Age Without Flinching

Alexander Payne and Jim Taylor adapted Rex Pickett’s novel and the film is unusually specific about a particular kind of failure: not dramatic ruin, just a man in his forties who hasn’t become what he expected.

The physical comedy is the cruelest part of that. Miles running naked from a house, Jack hiding in a vineyard, the two of them in a hospital, and none of it staged for glamour. These are two out-of-shape men making poor decisions in daylight. Jack is also where the film slips a little. Church is terrific, but the script keeps using Jack to set off the next disaster, and in the vineyard and hospital stretch he plays more like a plot engine than a man. Phedon Papamichael shot the Santa Ynez Valley in golden light and split screens, and the beauty of the setting is deliberately at odds with what is happening in it. Nobody in this film deserves this scenery. Rolfe Kent’s score is the other quiet decision. It’s jazzy and light, and it keeps insisting the film is a caper while the events get progressively worse. That’s what keeps the film watchable.

Payne had made Election and About Schmidt before this and would make The Descendants after, and the through line is people who are wrong about their own lives being observed without contempt. He’s the rare American director whose comedy has no cruelty in it and no forgiveness either.

It Moved the Wine Market

Sixteen million dollars, about a hundred and nine million worldwide, five Academy Award nominations and a win for Payne and Taylor’s adapted screenplay. For a film with no stars, almost no plot and two leads the audience is meant to see clearly, that’s a considerable result and major studios have funded very little like it in the years since.

The commercial afterlife is unusual. American merlot sales fell and pinot noir sales rose measurably after release, an effect economists studied and named after the film. A comedy about two men behaving badly changed what a country drank.

That happened because the film gave a mass audience a vocabulary and a position, and positions are easier to adopt than knowledge. Miles is wrong about merlot and the film says so in its final scene, and the audience took the opinion and left the correction behind.

There’s a lesson in that about influence and it’s not a comfortable one. Work doesn’t transmit its argument, it transmits its surface, and the surface here was a man being confidently contemptuous about a grape.

For Writers

Audiences adopt attitudes faster than they adopt arguments. If your character holds a wrong opinion attractively, expect the opinion to travel and the correction to stay behind.

That’s not a reason to sand off the attitude. It’s a reason to know it’ll happen and to decide whether you can live with it. The structural defense is to make the correction the ending. Sideways does exactly that and it still lost. That tells you how much weight a last scene carries against two hours of charisma.

Should you watch Sideways?

Yes, and watch the mother’s house scene closely. Everything the film later reveals about Miles is already there in about six seconds, unscored and unremarked.

It’s a 9 from me because it keeps finding worse things out about its hero without ever losing its sense of humor or its affection for him. The one thing keeping it from a 10 is Jack, who sometimes plays like a device for starting trouble, and Giamatti, Madsen and that paper cup more than make up for him.

Frequently Asked Questions

What is Sideways about?
Two middle-aged friends take a week-long wine trip through the Santa Ynez Valley before one of them gets married. One is a failed novelist and the other intends to be unfaithful, and both are worse people than the opening suggests.
What is the mother’s house scene?
Miles visits his mother for her birthday and takes money from her dresser while she’s out of the room. It’s unscored and unremarked, and everything the film later reveals about him is contained in it.
What does the pinot noir speech mean?
Miles describes pinot as thin-skinned, difficult, needing constant attention and only expressing itself in exactly the right conditions. It’s a self-portrait and nobody in the scene points that out.
What is the joke about the Cheval Blanc?
He’s been saving a 1961 bottle for a special occasion, and it’s a Bordeaux blend heavy in merlot, the grape he loudly despises. He drinks it alone from a paper cup in a fast food restaurant.
Did Sideways win an Oscar?
Yes, Best Adapted Screenplay for Alexander Payne and Jim Taylor, from five nominations. Virginia Madsen and Thomas Haden Church were both nominated and didn’t win.
Did Sideways really affect wine sales?
Yes. American merlot sales fell and pinot noir sales rose measurably after release, an effect economists studied and named after the film.
What is Sideways’s weakness?
Jack is written slightly broader than the other three and sometimes becomes a plot generator instead of a person. Thomas Haden Church is good enough that it mostly doesn’t matter.

About the Author
Richard Lowe, professional ghostwriter

Richard Lowe is a professional ghostwriter and author with 113+ books authored and 54+ ghostwritten. Before writing full time he spent 33 years in enterprise technology, including 20 years as Director of Computer Operations and Technical Services at Trader Joe's. He writes nonfiction, fiction and memoir, and works with executives and experts on books that build authority.

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Disclaimer

The views and opinions expressed in this blog post are solely those of Richard Lowe and are based on personal experience and research. This content is for informational purposes only and should not be construed as professional legal, financial, accounting, or business advice. Always consult with qualified professionals before making important business or legal decisions. Richard Lowe is not a lawyer, accountant, or licensed professional advisor, and this content does not establish any professional relationship.