For Pickett it was the amusing and sometimes heartbreaking way in which Miles and Jack make mistakes in their lives that made them so real and intriguing to him. “I believe people really feel for these guys because they’re failures,” he says. “We all have aspirations to live bigger and more glamorous lives yet so very few of us are able to reach those goals. I think deep down we all want Jack to get to his wedding without ruining everything and we want Miles to give into love and not analyze himself to death. We want them to come to a reckoning with life, even if it’s a little bit different than what they had imagined.”
Pickett’s personal fascination with California’s wines also wove its way into the story – especially as the divergent lifestyles of Miles and Jack became reflected in the age-old debate between Pinot and Cabernet, the one being complicated, layered and difficult to produce, the other far more hardy and easily pleasing. Says Pickett: “Jack is a guy who would put anything down his throat. But Miles is into Pinot which is both one of the most complex wine grapes and yet potentially one of the most disappointing. In a sense, Jack chooses to be indiscriminating and Miles chooses to be disappointed. Yet there’s no doubt they’re both in need of redemption.” Ironically, Pickett first started the story as a screenplay, and when that didn’t seem to be working, turned it into a novel. He shared an early draft with a long-time friend, producer Michael London. London immediately thought of Alexander Payne, taking the story full circle. “Alexander loves flawed characters,” London explains. “I knew he would like the idea of two guys who go to such an idyllic place on what should be a very happy trip only to find pain and misery as a result of their self-induced misadventures. And I had a feeling that Alexander would be able to take these wonderful characters and add even more depth and humanity to them.”
London also foresaw a more practical reason why Payne might connect with Miles and Jack's struggles. “Alexander was close to the age of the guys in the story, as was I. You come to a point in life where you’re smack in the middle of your existence, with as much behind you as ahead,” says the producer. “It’s a big moment. You've made real decisions and you can no longer hide behind fantasies of what you hope your life will be like in the future. That's what this story is about and I thought Alexander would have insight into it – not to mention that he also has a great affection for wine and the wine country.”
Payne, who at the time was just finishing ELECTION and about to embark on ABOUT SCHMIDT, continued to keep SIDEWAYS on his mind through those films. Despite his changing career, his commitment to Miles and Jack never faltered.
In adapting the novel for the screen, he and writing partner Jim Taylor found the main characters’ comic repartee ready-made for film dialogue. “This was probably the easiest adaptation we’ve ever done,” says Taylor, who typically takes turns with Payne typing at a single computer with two keyboards. “We drew a lot of the language from the book, because Rex already has such a cinematic way of writing.”
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