Rex Pickett’s Sideways Inspirations

Though famous for popularizing pinot noir across the planet, the film Sideways was actually first inspired by golf.

Rex Pickett, who wrote the novel that became the Oscar-winning film, was down on his luck in the 1990s. “That was a brutal decade for me,” said Pickett, whose life was in a tailspin. “I was very isolated and very alone. So I went back to the game of golf.”

He’d regularly drive from Santa Monica to play Sandpiper Golf Course in Goleta, where he heard about La Purisima Golf Course near Lompoc, but he wasn’t immediately keen on adding another 50 miles to his drive. “Finally one day, I just drove past Sandpiper and went to La Purisima, and I absolutely fell in love,” said Pickett. “That’s really the first inspiration for Sideways, even though I didn’t know it at the time. I really went up to play golf.”

He stayed at the Windmill Inn — today known as the Sideways Inn — and ate at A.J. Spurs and then the Hitching Post 2. “It looked like a biker bar from the outside when you first looked at it,” recalled Pickett, who’d sit at the bar and talk to owner/winemaker Frank Ostini, winemaker Chris Whitcraft, and others. “I started to find out this is wine country.”

He added wine tasting to his visits. “Bear in mind, back in those days, it was free, and I was dead broke,” he continued. “What I discovered that so many people in the greater L.A. area discovered later is that within two hours, you can be in this bucolic place. You can let your hair down. It’s relaxing. It’s beautiful. The skies are clear. There’s no traffic.”

He enjoyed the rustic tasting rooms of Foxen and Sanford the most. “There was a marriage of this sort of natural ethos, but then a sophistication in the wine,” he said. ”My life was really in a bad place, and it was very healing to go to the Santa Ynez Valley.”

He penned a mystery novel called La Purisima, but that wasn’t selling. He kept returning to the Santa Ynez Valley, occasionally visiting with a film set electrician named Roy Gittens, who became the inspiration for the film’s womanizing character, Jack. “There were no affairs, no naked women,” clarified Pickett. “We got to the end of a great trip, and Roy said, ‘You should write a screenplay about it.’”

So Pickett wrote a play called Two Guys on Wine, but it didn’t work. Meanwhile, he was learning more about wine to keep up with the snobs at a wine bar near his home, and decided to write a comedic scene in that setting that was full of sarcasm and repartee but devolved into a brawl.

“I literally stood up from my desk,” he said, realizing that writing about this world in first-person as a novelist — not in third-person as a screenwriter or playwright — was the voice he needed. “I’d had epiphanies before, but this was a big one.” He wrote the novel in nine weeks.

The film’s impact on pinot noir was immediate upon its 2004 release, and not just in the Santa Ynez Valley. “When I meet people in Sonoma, where I live now, they really get it,” he said. “They weren’t in the movie, but they make pinot noir, and they saw their sales go through the roof.”

Pickett parlayed the success of the film into multiple sequels and a theatrical version. He recently led the conversion of the original 35mm film into 4K digital resolution. “The colors are vibrant, there are no pops or scratches,” he said of that updated format. “You see into the shadows way better than you ever did.”

He’s visited the Santa Ynez Valley since, and will be back in October for a weekend of events at the Alisal Ranch, including dinners, a screening, golf, and horseback riding. But he seems to have soured a bit on the scene here.

“There’s no question that the pinot noir up here [in Sonoma] is superior,” claimed Pickett. “There are some good ones in the Santa Ynez Valley, but I think they’re getting by on the hype of the movie.”

I told him that was quite counter to the opinion of most professional critics (myself included) these days — even many Sonoma-based winemakers make Santa Ynez Valley pinots today, for instance, as do some Burgundians. But he didn’t budge, alleging that many winemakers down here add syrah or water back their overripe pinots. That may have been true in the early 2000s, when the ripeness trend was in full swing, but I rarely hear of that or taste anything like that today, when so many pinots lean into lightness rather than power.

“That’s the wonderful thing about wine,” said Pickett. “It’s like film or theater. We can argue and choose to agree or disagree. The conversations are what I really love. Everyone’s palate is different.”

He does credit the Santa Ynez Valley for using Sideways to its collective advantage. “They have leveraged the phenomenon brilliantly,” said Pickett.

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Rex Pickett is hosting a Sideways screening at the Sebastiani Theater in Sonoma on Oct. 11. Click here for those details. He’ll be at Alisal Ranch in Solvang, Oct. 18-20, for a full weekend of Sideways events, including wine tastings, dinners, golf, and horseback rides. See alisalranch.com/experiences/sideways-anniversary. For more of his books, see rexpickettbooks.com.