When Rex Pickett got the word that Alexander Payne, fresh off the box-office success of Election, was optioning his unpublished novel for his next film, he’d just had his credit card declined for a $6.50 charge at Baja Fresh in Santa Monica. The manuscript about two friends floundering through wine country that landed on Payne’s desk would become Sideways. Like Miles Raymond, the main character in the book and film, Pickett was an unpublished author living in L.A. and spending time in Santa Ynez Valley—a regular at the Hitching Post, staying at the Windmill Inn (now called the Sideways Inn) and a devoted disciple of Pinot (which he spent hours talking about with Richard Sanford). And before you ask: No, he wasn’t drinking any Merlot.
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What is it like when you go to the Hitching Post—a central location for both the book and movie—now? How different is it?
Pickett: Totally, radically different. They give me the “A” table right by the grill, and it’s crowded. The bar is two to three people deep … When I go down there now, it’s a zoo, but [in the ’90s] there was nobody there.
Sideways was an appreciation of wine, certainly, and Santa Ynez as a place, coupled with an element of the parody of wine snobbery. But how has the series developed, now that you’ve written three more books— most recently Sideways: New Zealand—about Miles’ adventures?
Pickett: It’s definitely my story, I guess. Because I write in this autobiographical way. When I wrote Sideways, I was in such a state of despair and living on the edge, and also getting older. I thought if I can marry despair with humor, there might be a magic there.
So, it’s my story. I feel an obligation, though, that wine be part of it because it’s associated with it. In fact, they wanted to do a TV version with Miles living in Brooklyn or something, running a coffee shop. And I nixed that idea, just totally nixed it.
I think one of the things that drew me to wine is that it inspires. People say Miles is a snob, but really, he’s not. If you read the novel, he’s living on the edge. And I think Payne shaded him a little bit more toward snobbery because he wanted to poke fun at him. And I get it. I don’t have a problem with it. But the truth of the matter is that, for me, wine has a major [accessibility] problem. And as much as I love wine, with literature or cinema, that’s a democracy. In other words, you and I and everybody else can all watch Godfather, Chinatown, whatever, develop a film sensibility. We can all read great literature. But we can’t all drink Chassagne-Montrachet verticals every night.
But at the same time, I do feel that Miles is synonymous with wine. To take wine out of the equation would be a betrayal of the fan base.
He wants to believe in something —and he believes in Pinot Noir.
Rex Pickett
He’s also synonymous with a certain iconic line. And maybe a two-decade-long effect on wine, wine tastes and the fate of Pinot.
Pickett: Alexander Payne made the movie. Miles’s love for Pinot Noir, Alexander honored that exactly. Rex’s love for Pinot Noir through his character, Miles. He honored it. He didn’t satirize it. He didn’t abase it.
Miles really doesn’t have anything. All he’s got is this book and one last publishing house that maybe is debating whether to publish it or not. He’s clinging with his fingernails to that. But he wants to believe in something—and he believes in Pinot Noir. There’s an escapism in having that belief. Today it’s sad: People play video games, and that’s their escape; or they watch crappy TV. But for Miles, Pinot Noir is something he can get into: It’s more than a hobby, it’s a passion, almost a religion, and there’s nothing wrong with that. We all want a belief system. We know that churches are closing every day. Religion is breaking down everywhere, but we all look for these belief systems. For Miles, his belief system is Pinot Noir. He loves it; it’s as simple as that.
What’s next for Miles? Could book five may start in Napa, where you now live?
It’ll start at the Vintner’s Collective here. Miles is going to the Sideways: 20-year reunion. Although it’s another title in the book. But that’s who he is. He’s now a successful author. This has been in book two, and his book has been made into a movie, and he’s wildly successful, whatever, but now he’s blown all his money on women and probably fancy bottles of wine or whatever. And why not start in Napa and have him head back south? And so that will be the next novel. It’s going to be called “Sideways: 20.”
This article originally appeared in the April 2024 of Wine Enthusiast magazine. Click here to subscribe today!
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