Double Take: ‘Sideways’ (2004)

In Sideways, the two Steves find hints of satire, legs of oaky '70s cinema, a bouquet of gender commentary, and a chewy finish.

Steve Leftridge: What stays with me about Alexander Payne films — Citizen Ruth, Election, About Schmidt, Sideways, The Descendants, and Nebraska — is that, while I don’t tend to notice anything from a technical standpoint that marks them unmistakably as Payne movies, they are distinct in how their narratives unfold and how their themes emerge within those narratives. I don’t think any other director could have made Sideways, peculiar and deftly arranged as it is. At the same time, I have trouble putting my finger on exactly what makes Sideways and Payne’s choices so original and idiosyncratic. Can you assist, Mr. Pick? What did you notice with this one that stands out?

Steve Pick: I can only say that Sideways is a lovely entertainment. In essence, it’s a romantic comedy, but one told entirely from the male point of view. Miles is the dreamer, the one who sees life as potentially richer than those around him, but who is depressed because his relationship ended a year before. Jack lives in the moment, so much so that he only cares about consequences of his actions after they lead to conflict with another. It’s sort of an Odd Couple template, without the gay slurs about Felix.

I found it interesting that these two characters are in their mid-30s and not yet settled in their lives. They are creative types who have little-to-no chance of achieving success. Miles the writer has published nothing. Jack the actor had a small part on a soap opera years ago and is now relegated to the occasional TV commercial. It’s unusual to find a film that focuses on people of that age and ilk. It’s also unusual that, though Jack is played for laughs, and Miles is played for sentiment, neither one is looked down upon. Payne is sympathetic towards both characters and is interested in letting us see both their charms and their flaws.

In that spirit, I’m interested in looking at the good and the bad in this film. One potential downside of Sideways is the limited motivations for the women in it. Virginia Madsen and Sandra Oh (not yet a Gray’s Anatomy star, but familiar to those of us who couldn’t stop watching the mess that was Arliss) are so wonderful in their roles as love and sex partners that it’s possible to forget that we don’t quite understand what’s driving them to do what they do except as reacting to the equally mesmerizing Paul Giamatti (familiar after the previous year’s American Splendor) and Thomas Haden Church (who could be funny in TV sitcoms). What’s your take on Maya and Stephanie, or for that matter on Miles’s ex, Victoria?

Leftridge: Oh! That’s a relevant question to any of Payne’s films, focused as they are primarily on middle-age men going through crises that often revolve around women. Payne’s male characters are depicted as being dependent or otherwise enmeshed with women but are badly damaged by these relationships. In my view, Payne draws the women in Sideways sympathetically; it’s the men who are the trainwrecks. Stephanie and Maya are both intelligent, independent, cool women. They are friendly and adventurous and like to have fun, but we see both women stand up for themselves when they have to. They are round characters. Stephanie, for instance, is a single mom, has an eclectic home decor style, and drives a motorcycle. When that motorcycle mama lays her big spike down, she breaks Jack’s nose.

I find Maya even richer as a character (thanks in large part to Virginia Madsen’s subtle performance). Maya is divorced and childless and working on her master’s in horticulture while waiting tables at The Hitching Post. She’s someone who, like Miles, could use a rebound connection, but unlike Miles, she exudes a self-possession that contrasts with Miles’ neuroses.

Which brings me back to the men. Miles and Jack are fun to watch and have a certain hangdog likability, but they act like jerks a lot of the time, don’t they? Is this a “guys’ movie” in the sense that female viewers are unlikely to find any redeeming qualities about these two dudes?

Pick: I’m not sure I find much redeeming about Jack and only some things redeeming about Miles. I had no sympathy for Jack’s neediness, his inability to focus on anything but what is in front of him, or his harsh treatment of his best friend. Frankly, it’s hard to imagine that he stayed in a relationship long enough to be so near marriage, since it seems likely he would stray any time he was out of his fiancee’s sight. If he were my friend, I suspect I would have left him in wine country some time on the second day.

Miles, on the other hand, is so hung up on his ex-wife that he can barely function, which makes him hard to root for, too. The obvious connection between him and Maya, however, was pleasant to watch, until he was caught in the lies Jack had told. The scene between Miles and his ex at the wedding was excruciating. He had obviously learned nothing except shame, which made his potential triumph at the end unearned. I couldn’t see any good reason for Maya to offer to see him again. Of course, we could only take her word that his novel was better than what all the publishers in the U.S. thought it was.

For me, the best parts of the film were little bits. Every time Jack tried wine at a tasting. The conversations between Miles and Maya. The delight Sandra Oh’s character took in Jack’s charms. The insanely over-the-top comedy of the naked man running down the street. Even the sweetness of Miles walking up those steps at the end, despite my feeling that he hadn’t earned even a chance at redemption. These and other things like them added up to a pleasant film about two less than pleasant people. Which is good enough for me, but I’m curious as to how it became as popular as it was. Do you think more of the audience rooted for Miles to win, or for Jack to get a comeuppance?

Leftridge: Miles is a mess, of course, but I think there’s an honesty to the way his character is depicted that makes him refreshing and relatable and worth rooting for. Maybe Miles resonates mostly with men, who can perhaps more easily relate to the pressures Miles feels to live up to traditional roles as a husband and a careerist and a masculine specimen. As the film tracks Miles’ insecurities about how well he’s meeting those expectations, the truth, as you suggest, is really in the details: Miles reading on the toilet when he’s already late; wallowing in his depression by watching golf on the motel-room TV; sleeping in his clothes; keeping up with the latest issue of Barely Legal; agonizing over his failed marriage and unpublished novel and awkward first kiss with Christine, etc. So maybe you’re right that Miles doesn’t “deserve” another shot at Christine, but it’s nice to think that a guy who makes a lot of mistakes and who lives in the grips of anxieties and insecurities gets the kind of second chance that he does. But we have no guarantees that he won’t fuck up that chance, too.

My question for you is about how wine drinking is presented in the film. Miles is an alcoholic, right? Yet the film was credited with giving wine consumption, particularly the sales of the Pinot Noir varietal, a boost. What’s your take here? Did it make you want to reach for a bottle or did you see Miles’ alcohol abuse and dependence as disturbing?

Pick: I’m not sure I agree Miles is an alcoholic. I think he’s depressed, and I think he sometimes uses alcohol to self-treat that depression (which doesn’t work). But there are only two scenes I can think of in which he overdoes the wallowing in misery to which he is prone. The rest of the time, I think he is genuinely enjoying wine for all the reasons he says he does (including the pleasures of being a bit drunk). My palate is perhaps a bit better than Jack’s, but nowhere near as developed as that of Miles. But the many scenes in wineries, the downright pleasurable tastings shown in the film, are enough to make me want to know more. I can easily see why wine consumption went up at least in the month or two after the film was new.

Twelve years after seeing Sideways in the theaters, I had pretty much forgotten the basic plot, but I remembered the scenes at wine tastings. It’s interesting to think Payne was more focused on the idea of two men at a crossroads in their life — in their 30s, failing in their creative careers, not clear how to proceed romantically, drifting apart from the things they had in common in the first place — but it was his decision to set the film on a trip to wine country that made it a success. I think even with the aforementioned scenes of Miles falling towards the bottom (but not getting to the rocks), Sideways romanticizes wine. The way the light hits the pinot noir in those glasses, the beautiful landscape shots, the convivial aspects of conversation fueled by wine — these are elements that stick in the mind long after the rest of the film might fade.

As somebody who knows more about Payne than I do, how do you see Sideways within his oeuvre?

Leftridge: First the wine thing: I think you’re on to something in that Payne plays it in the middle. On one hand, the connoisseurship of wine is compelling — Miles’ and Victoria’s passion for the grape as both an intellectual and epicurean pursuit looks like a lot of fun. I love those groovy montages with all the split screens that depict the orchards — all those sunsplotchy shots and the ‘70s-sitcom-sounding tunes, like those old Sesame Street segments when they showed people manufacturing stuff.

The scenes of Miles tasting wine are hilarious — holding his finger over his ear when trying to identify the wine’s tones, like he’s trying to sing harmony. As opposed to Jack, who chews gum while he’s sampling wine. Plus, Miles’ speech to Victoria about pinot noir is special: its grape is thin-skinned, temperamental, needs constant care and attention, but if someone really takes the time to understand it, it can thrive to its true potential. We realize that the pinot is a symbol for Miles himself.

On the other hand, there are some scenes in which wine isn’t working for Miles. The reason he’s late to pick up Jack in the first scene is that he’s hungover. He slams an entire bottle of wine in about two minutes when he finds out that his ex-wife has gotten remarried. These characters drink a lot — like when the foursome enjoys six or eight bottles of wine at dinner, before they go back to Mya’s to drink even more. It’s all spirited partying, but it also inspires Miles to drunk dial his ex-wife, rendered in extreme sweaty closeups and shaky handheld cameras that perfectly capture the lows of being high. When Miles finds out that his novel won’t be published, and he subsequently can’t get a full pour at the tasting counter, he drinks from the spit bucket.

As for Payne, if you like the hazy pace and the eye for realistic detail, the candid look at human behavior, the psychology of existential crises, and the left-of-center humor, then Payne’s your guy. Election, About Schmidt, Sideways, The Descendants, and Nebraska are all about men who reach a point in their lives when things get knocked askew in unpredictable ways and they’re forced to figure out how they’re going to survive their current emotional paralysis and what the rest of their lives are going to look like. Their search almost always involves a road trip. If you’re like me, you’ll enjoy riding along with Payne over and over again.

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