Sideways is adapted from the novel of the same name by Rex Pickett.
The novel took a lot of inspiration from Pickett's life during the early-mid 1990s. In Pickett's own words:
'Back then, the Santa Ynez Valley was a little known wine region north of Santa Barbara. Maybe 50 wineries – now more than 250. Very little pinot noir had been planted in the 90s when I started sojourning up there, first to play golf, then to get familiar with the wines. I loathed Los Angeles and the cruel film industry that had brought me so much misery. So I would throw my golf clubs in the car and take off. Soon, instead of golfing, I went wine tasting. I hung out at the Hitching Post restaurant and befriended local winemakers. My fascination deepened. I discovered small, ramshackle tasting rooms in this sylvan paradise a mere two hours from the horrors of LA, and I thought: “This is heaven.”
On one trip, I brought along my friend Roy Gittens, an electrician on my failed second film. We went wine tasting. I made him laugh. Tasting room after tasting room. More wine. And some golf. And ostrich and pinot at the Hitching Post. At some point during that trip, he suggested I write a screenplay about guys who go wine-tasting. Galvanised, I wrote a screenplay called Two Guys on Wine. I didn’t like it. There was something about it that didn’t work.'
Two Guys on Wine eventually became the novel Sideways.
The above quote is from this article by Pickett at https://www.theguardian.com/stage/2016/may/15/sideways-author-i-was-ready-to-shoot-myself-then-i-found-pinot-noir
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