Filmlab: Best Movies about Writing – Sideways

Everyone has a novel in them, but not everyone has a novel in them that people want to publish. That’s the hard truth Paul Giamatti’s failing writer Miles is facing in Sideways, Alexander Payne’s delightfully discomfiting 2004 road movie about two middle-aged friends on a week-long tasting trip through California’s wine country. The excursion is a last hurrah for the about-to-be married Jack (Thomas Haden Church), an ageing lothario and fading soap star on a mission to sow the last of his wild oats. Miles, his old college roommate, has organised the trip to indulge his own love of pinot, with his epicurean pretensions a socially acceptable cover for the alcoholism he’s embraced in the wake of a failed marriage, an unsatisfying teaching career and his ongoing literary frustrations.


His latest tome, an unwieldy, experimental novel about his father’s stroke that even Miles can’t summarise, has already done the rounds of the bigger publishing houses. Now it’s working its way up the editorial chain at a small independent publisher, with Miles anxiously awaiting news of its fate as he embarks on his bender. He’s been through this before and insists he no longer cares. Yet he knows, on some deep subconscious level, that there’s a time limit on potential, a moment when something that could have been great will never have the chance to be.

Sideways, which Payne adapted from failed Hollywood screenwriter Rex Pickett’s semi-autobiographical novel of the same name, explores this crisis via extensive wine metaphors and Giamatti’s pitch-perfect performance. The latter riffs on the actor’s misanthropic turn as Harvey Pekar in American Splendor, but he’s simultaneously much sadder and funnier here. No longer is he playing an irascible outsider who finds his voice and discovers he has an audience to boot. Instead, he’s the schlubby everyman no-one wants to be – the one who dreams of making his mark but spends too long contemplating how to go about it for it to ever become a reality.

When Miles discusses his most prized wine – a 1961 Cheval Blanc – with a fellow oenophile called Maya (Virginia Madsen), the results are excruciating. Their subtext-laden conversation about the versatility and complexity of fine wine – the way it’s alive and changes its taste depending on when the bottle is opened, the way certain grapes need special nurturing, the way any good wine always has a chance to taste spectacular, right up until the moment it peaks – ends with Maya all but inviting Miles to make a move. When he freezes, instant regret and simmering self-loathing immediately lead him to make the situation worse by trying to recapture the moment, having already thoroughly killed the mood. Even in his booze haze he’s starting to figure out that life doesn’t work the way fiction does: he can’t just rewrite a scene to make it perfect.


Miles has other problems too. His innate snobbery comes off as an unpleasant defence mechanism and his pseudo-intellectualism reflects deep-rooted insecurity. The name of his book, for instance, is The Day After Yesterday, a magnificently awful title that manages to be simultaneously pretentious and obtuse. “Oh, you mean today?” asks Maya, her malice-free bewilderment upon hearing it immediately puncturing his own self-regard. And yet, apparently, Miles can actually write. His agent sounds genuine when she tells him the publishing industry has become gutless and that he shouldn’t be discouraged. And Jack – always a glass-half-full kind of guy with no delusions about his own acting career – implores him to self-publish and get it reviewed, screw the industry.

But it’s only when Maya finally finishes all two boxes’ worth of his unbound manuscript that he finally begins to learn from his mistakes. She still has misgivings about that title, and she’s not keen on the confused ending, but she does like the way he writes and sympathises with the heartache he’s clearly experienced. Her empathetic critique – left on his answering machine months after everything goes south between them – prompts the ambiguous final shot of Miles attempting to do in real life what people like to read about in fiction. He’s seizing the day, not abstractly wallowing in the day after yesterday.

Alistair Harkness is a film critic for The Scotsman. You can follow him on Twitter here.