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A Life in 5 Bottles

5 Life-Changing Wines From ‘Sideways’ Author Rex Pickett

The man who changed California wine reveals the wines that changed him

David W. Brown By January 13, 2022
Sideways author, Rex Pickett, drawn on label of Merlot bottle
Illustration by Ananda Walden

Rex Pickett wrote a novel from his heart, “Sideways.” 

Everybody hated it.

It was inappropriately personal, said one. Another advised him to burn it. One editor asked why he even bothered submitting it. In all, Pickett received over 230 rejection letters. When it finally sold, it was for an insulting $5,000 — and the publisher acted like they were doing him a favor. 

The story follows aspiring writer Miles, and his best friend Jack, on a road trip through Santa Ynez wine country in California. Jack is engaged, and this is a celebration of sorts. For Miles, a devoted Pinot Noir drinker, it is a journey of self-discovery.

And yet, it changed the wine world.

"I bared my soul. It hurts to be pushed aside when you’ve offered up something so personal."

Rex Pickettauthor of “Sideways”

Out of the slush pile

While the “Sideways” manuscript was limping along in the publishing world, it was also festering in the slush pile at film director Alexander Payne’s office for over a year. Pickett’s agent called it roadkill. But Brian Beery, an assistant to Payne, stumbled upon it and convinced the director to read it. Payne took it with him on a flight to the Edinburgh Film Festival, and read it on the way back.

“I had just come back from a chain food dive known as Baja Fresh where my credit card was declined for a $7 purchase,” says Pickett. There was a message on his answering machine. “I call my new agent, Brian Lifson, and he’s screaming on the phone: ‘I don’t believe this! Alexander Payne just got off a plane and ‘Sideways’ is going to be his next movie!’”

The film has since grossed $650 million and changed the way Americans drink wine. 

Just ask Merlot producers.

In the early 1990s, American wine drinkers were Merlot crazy because of the reported health benefits of red wine. Merlot was cheap and quaffable, and winemakers were happy to oblige the public’s thirst.

“When I wrote it, Merlot was 20% of sales in the United States, more than any other country. It was overcropped, with mechanized farms, and riding down conveyor belts with reptiles and leaves,” says Pickett. 

Insiders knew better. “When I was writing ‘Sideways,’ I’d go to these wine tastings, and if you just mentioned Merlot, it was tantamount to admitting you were a wine Philistine or a wine ignoramus.”

Miles, the central character, was anything but an ignoramus. A key moment in the novel and film involves Miles threatening to leave the restaurant if the women they are meeting order the dreaded M-word. “I am not drinking any f‐‐‐ing Merlot!”

The aftermath

The wine business endured a subsequent Sideways effect. Paul Giamatti’s iconic condemnation of Merlot depressed its sales, while simultaneously boosting Pinot Noir. 

Despite its difficult start, “Sideways” has spawned two sequels, “Vertical,” and “Sideways 3 Chile,” a blockbuster stage play presently touring in Spain; as well as a musical with Tony Award-winning director Kathleen Marshall attached to direct. There is even a Sideways line of Chilean wines. Pickett is at work on a fourth Sideways novel that will take Miles to New Zealand.

Rex Pickett changed the wine world. Here are 5 wines that changed him:

bottle of Beaulieu Vineyard Georges de Latour Private Reserve Napa Valley Cabernet Sauvignon

Beaulieu Vineyard Georges de Latour Private Reserve Napa Valley Cabernet Sauvignon 1962

“Everyone in the wine world has their epiphany wine,” says Pickett. When he was a teenager, he and a friend went to Europe, where they developed their palates for beer. Back in America, he thought he might like to try a bottle of wine. Being underage, there was no way he could buy it, so he did the second-best thing: He stole one. While his friend distracted the shopkeeper of the low-end liquor store, he went to the back and grabbed the most expensive wine he could find: a 1962 Beaulieu Vineyard Georges de Latour.

“I’ll never forget,” he says. “We went up to a rooftop deck of our two-story apartment at night, and I opened it and we sat up there under the stars, two blocks from the beach, the waves crashing. And I go, Mark, what the heck is this?”

Pickett says that bottle opened new neural pathways, and there was no going back. He compared it to a quote about heroin from famed jazz musician Charlie Parker, “You can get it out of your body but you can’t get it out of your mind.”

Current vintage: Beaulieu Vineyard Georges de Latour Private Reserve Napa Valley Cabernet Sauvignon 

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bottle of Silver Oak Alexander Valley Cabernet Sauvignon 2016

Silver Oak Alexander Valley Cabernet Sauvignon 1992

The night a colleague opened an aged Silver Oak Cabernet Sauvignon led to a revelation for Pickett. “Silver Oak is a Napa wine, of course,” says Pickett, but the same, he says, applies to Bordeaux-based wines. “The ability it had to age, and what they do, is truly transcendent. I remember thinking, silky fruit in the mouth, the tannins …” He trails off, and recites one of Miles’ lines from the Sideways stage play, “The tannins have slipped away and like Icarus has risen on wings of wax to the burning sun of greatness.” 

When a character observes that Icarus plummeted to the earth and drowned in the ocean, Miles says, “Yes, but not before he had tasted immortality. This wine merits fatalism.”

Current vintage: Silver Oak Alexander Valley Cabernet Sauvignon 2017 

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bottle of Sanford Winery Sta. Rita Hills Pinot Noir 2019

Sanford Winery Sta. Rita Hills Pinot Noir 1994

Back in the 1990s, when “Sideways” was still maturing in Pickett’s mind, he frequented the Sanford Winery Tasting Room. There, he first fell in love with a wine that would in large part define the rest of his life: a Sanford Winery Pinot Noir. 

When writing “Sideways,” Pickett needed Miles to have something to believe in, because the character had given up on writing, women — even life. “We all have to have a belief system, otherwise life isn’t worth living. And Miles lives for his passion for Pinot Noir.” 

But that vintage that so enraptured Pickett? It was big and bold and didn’t taste the way Pinots are “supposed” to taste. The wine wasn’t even 100% Pinot Noir; a California wine needs only 75% of a variety to be listed on the label. The bottle that would one day send sales of Pinot surging was actually 25% Syrah. “So when Miles is discussing his passion, I am rhapsodizing about a wine that isn’t even 100% Pinot Noir. But I think it really was one of the first Pinots that moved me. It had that richness that Syrah brings to wine, that huge fruit heft.”

Current vintage: Sanford Winery Sta. Rita Hills Pinot Noir 2019 

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bottle of Casa Marin Single Vineyard Cipreses Sauvignon Blanc 2010

Casa Marin Single Vineyard Cipreses Sauvignon Blanc 2010

While researching the third Sideways novel, set in Chile, a wine tour was set up for Pickett that included factory-sized wineries. And while they rolled out the red carpet for Picket because they wanted their wines featured in a Sideways novel, these were the exact opposite of the wineries Miles would have visited. “I wanted to find the off-the-grid people, but the places they had me going … Well, I almost got back on a plane after a week down there.”

But he heard about a winery about three miles from the Pacific Ocean, in the town of Lo Abarca. María Luz Marin had started a winery there 30 years earlier, becoming Chile’s first female winemaker and winery owner, and someone recommended that Pickett check it out.

When poured a glass of Sauvignon Blanc, he says it looked like water. “It had such floral characteristics, and it was kind of shy, because it had such bright acidity. I said, ‘Holy s‐‐‐!’ and then they started pulling out older ones. I never knew Sauvignon Blanc had ageability. But oh my god, it does.” He would have left Chile, he says, had he not met her. The novel was saved.

Current vintage: Casa Marin Single Vineyard Cipreses Sauvignon Blanc 2015

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bottle of Blue Farm Sonoma Gap’s Crown Pinot Noir 2019

Blue Farm Sonoma Gap’s Crown Pinot Noir 2019

While visiting Santa Rosa, a friend promised to take Pickett somewhere special. That place was Blue Farm Wines in Sonoma. They didn’t even have a tasting room: just a picnic table overlooking a pond and vineyard. While each wine was delicious, it was something Blue Farm’s founder, Anne Moller-Racke, said that was an epiphany. 

Pickett remembers her saying her Pinot Noir was like a watercolor, while Cabernet was like an oil painting. One can slap on Merlot, or slap on Syrah. The poetry of her words somehow caused Pickett to fall in love with Pinot Noir all over again. The grape’s delicacy, its sadness, and its ability to break hearts. 

Current vintage: Blue Farm Sonoma Gap’s Crown Pinot Noir 2019

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