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Uncorked: 'Sideways' author ready for next step

The waiting game had to be over for Rex Pickett.

His novel “Sideways” won an Academy Award for Best Adapted Screen Play, a Golden Globe Award for Best Motion Picture and a slew of other industry honors. Pickett thought he had arrived. Gone were the days of living as a starving artist who borrowed money for rent and struggled to get attention as a screenwriter and author.

Or so he thought.

Bumming rent money was no longer an issue. But after the “Sideways” hoopla died down, Pickett, who has endured a series of trials and tribulations in his personal life, couldn’t catch a break in the film or publishing industry.

Armed with a self-depreciating sense of humor, he persevered and has reached a career apex. The follow up to “Sideways,” “Vertical” is due out Nov. 21. With a solid investor in place, Pickett feels he can give “Vertical” a proper release.

“On my epitaph I joked it would say, ‘Rex is still waiting,’” Pickett deadpanned. “I was always waiting for a publicist, an agent or a screenplay to get the green light. But not any more, I feel like I can make things happen now. This time I have an investor, social media and the right publicity.”

Pickett is riding a recent wave of success. In addition to “Vertical,” he’s also working on a pilot for HBO about wine critics from Leverage Management. His screenplay, “Repairman,” might shoot this spring as an indie film.

I talked to Pickett by phone on Tuesday.


Things couldn’t get any worse for Rex Pickett. Then he had a moment of clarity.

He decided to write a short story about his experience wine tasting, dining and playing golf in the Santa Ynez Valley, his favorite vacation destination for about 10 years.

In an instant, “Sideways,” which became a diversion from a divorce and impending financial doom, was born.

“I wrote the novel as pure escapism,” Pickett said. “I just needed to make myself laugh for four hours a day. I wrote it in nine weeks, but it was really 10 years of what I had absorbed in traveling to the area.”

For Pickett’s next novel, it would be easy for him to write a boilerplate remake of “Sideways.” With all of its acclaim, common sense dictates a similar novel would be an instant best seller – Pickett sold “Sideways” for $5,000 and only made $60,000 on the novel – and the big press houses would be happy to have an instant-hit cash cow.

But Pickett, who decided to be a writer when he was 18, is passionate about character development. In “Vertical,” a now successful Miles and soon-to-be divorced Jack make their first stop in Oregon’s Willamette Valley.

It’s the start of a cross-country trip to visit a stroke-stricken Mrs. Raymond, Miles’ mother, who is stuck in assisted living in Wisconsin (a synopsis is available at

“‘Vertical’ is just as funny as ‘Sideways,’ it’s just harder hitting,” Pickett said. “I want to take the characters to another place. It’s not a ‘Sideways’ retread. ‘Sideways’ was a very personal novel because I like to write what I know about and put characters in settings I know.”

What to buy

Visit to order the new book. Pickett has a blog, which has many whimsical “Miles-esque” observations. There also is an event schedule on the website.

Wine 101

“Sideways” grossed $250 million and blasted a popular varietal in a pivotal scene.

Lots of people heard Miles utter a few choice words for merlot.

It would be easy to think Pickett hated merlot based on that famous scene, but the author was quick to mention some of the world’s finest wines are merlot.

He doesn’t hate merlot, but he does sound like a pinot noir kind of guy.

• James Nokes writes a bi-weekly wine column for the Daily Chronicle. He’s been tasting, touring and collecting in the wine world for several years. Contact him at

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