Sideways, 16 Years Later

I want to like Sideways, I really do. Alexander Payne’s 2004 film, which tracks Paul Giamatti’s Miles and Thomas Haden Church’s Jack across a bachelor party tour of California wine country, spends much of its runtime celebrating writing and creation. It’s just the kind of movie someone who writes a blog that is partially about storytelling should love. The first time I saw Sideways I was a teenaged blockhead who had no chance of appreciating it but when it was recently recommended by a friend whose artistic opinions I respect, I decided to rewatch it. To my surprise, that rewatching only confirmed what dumb teenage me already knew: I don’t like Sideways. Let me tell you why.

Sideways is a film about being an adult. Let me rephrase that. Sideways is a film about some of the ways that you might be an adult. The film is centered on Miles, a junior high English teacher and, more importantly, an as yet unpublished author. That second item and its implications of failure are used as a framing device to depict Miles as a woebegone underachiever. As I sit here, blogging about a 16 year old movie with a half dozen incomplete novel manuscripts just a few clicks away, it’s a depiction that hits uncomfortably close to home. Miles overthinks and underperforms, he worships minutiae that few others notice and he rejects the views of the masses. Miles is me, of course, or at least some hypothetical and miserable version of me. Maybe he’s you, too. He’s also terrible. This is not why I dislike Sideways.

Considering its focus on wine culture, Sideways‘ best moments feature a suitably dry bacchanalian humor. Miles is meticulous and passionate, a nerd with whom I can relate. In one of my favorite scenes, he waxes on about the characteristics of a wine that he and Jack are tasting. Jack is clearly disinterested but trying to be a good friend, attempting to appreciate Miles’ insight and to carry on the conversation. They savor the wine’s aroma and flavor and only when Miles steps out of his own mind and stares at Jack for a moment does he realize that his friend is (supportively) pretending. “Are you chewing gum?” he shrieks as the scene ends. There are quality writerly jokes, too. One mocks the prospect of asking your friends to read revision after revision of your 800-page manuscript, another pokes fun at the terrible title that Miles has chosen (and which he believes to be profound), while yet another eviscerates that bane of writers describing their work to anyone else: “It’s difficult to summarize,” says Miles when his love interest inquires after the novel that has been his life’s ambition.

These bits of straight-faced hilarity come and go. They are minor parts of the action. The narrative’s focus is instead on the masked immaturity of its two main characters. Miles and Jack are adults dealing with adult problems like divorce, infidelity and career viability, but the two college roommates bring out in one another a maturity level befitting the dormitory. They get drunk and chase women, making fools of themselves in the process. A prominent scene plays a heavyset man’s naked, flopping penis for laughs. Miles and Jack are old now but they never really grew up.

And here is where Sideways loses me. Miles and Jack are, pretty uniformly, selfish, immature assholes throughout the movie, most often to everyone else but occasionally to each other. They are both revealed to be cheaters. Miles’ infidelity ended his marriage prior to the film’s events and Jack’s philandering consumes much of his screen time. They lie to most everyone they meet, often egregiously. Miles steals from his mother, moments before she offers to give him money. Jack intentionally crashes Miles’ car. These men are terrible to themselves and to everyone around them. They face no consequences.

Superficially, Sideways suggests that both Miles and Jack must deal with the ramifications of being assholes. Miles hits what we’re led to believe is rock bottom, drinking his most prized wine out of a styrofoam cup in a diner. Jack has his nose broken by one of his mistresses. But if either character changes from these experiences, if either of them grows in any meaningful way, we don’t see it happen. In one scene Jack is lying to his fiancé and the next time we see him, he’s getting married without incident, his bride blissfully unaware of his cheating ways, his broken nose explained by Miles’ crashed car. Miles mopes and wallows until the love interest that he lied to earlier in the film calls him, unprompted, throwing him a lifeline that he has not earned.

Stories don’t need happy endings and characters don’t need to become better people. Fiction doesn’t need to moralize. But there should be meaningful consequences for a character’s action and corresponding character growth. Otherwise why should I care about the story? At the end of Sideways, both Miles and Jack get their happily ever after despite neither having cleaned up or even necessarily learned from the messes we just spent two hours watching them make. We’ve seen no evidence that they’ve changed.

That disconnect irritates me and keeps me from finding joy in a movie that critics and friends adore. Why tell a story where actions have only temporary consequences? What’s the point? Sideways suggests that what we do matters less than who we are. And if you’re the white male lead of a film, you’re going to get the girl, regardless of what you do. The women of Sideways, the love interests and mothers and ex-wives, deserve better. Sideways is a dark comedy but if this is the film’s final joke, that women are forced to choose terrible men because all men are terrible and unchanging, it seems too bleak to inspire laughter. But perhaps, given recent events, it’s a fitting theme all the same.

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