Talking Vertical With Sideways Scribe Rex Pickett

Posted on Oct 28 by SEASONS Magazine

By Leslie Dinaberg

When it hit the big screen in 2004, the film Sideways changed Santa Barbara wine country‘s fortunes forever, increasing the cachet of our region’s winemakers—particularly those who make pinot noir—as well as considerably boosting their coffers.

For the author of the film’s source material, a semi-autobiographical novel of the same name, the post-Sideways trajectory has been a bit bumpier.

Vertical and Sideways Author Rex Pickett. Courtesy Photo

Vertical and Sideways Author Rex Pickett. Courtesy Photo

“People think I’m rich,” says Rex Pickett, affably chatting on the phone with me from his one-bedroom apartment in Santa Monica. “I live a modest life … I made less than 100 grand off of that book.” Though he did make more from selling the film rights, the novel was still unpublished when the movie was about to come out and Pickett says he was pressured by the movie studio (Fox Searchlight) to sell the rights for just $5,000, a decision he regrets today.

“If I had waited and rolled the dice when that movie came out, I’ve been told by numerous publishing agents that it would have gone for a million bucks. Had I just said no to five grand—and I almost did.”

The road to publication for his newest novel, Vertical, was not much smoother the second time around. Originally sold to Knopf, where his editor told him, “if you had that ending, we will not publish your novel,” Pickett decided to retain his creative vision and go it on his own, ultimately finding an investor and creating Loose Gravel Press.

A wildly entertaining and surprisingly poignant sequel to Sideways, Vertical takes place seven years later. Miles, like Pickett, has written a novel that has been made into a wildly successful movie, and the movie has changed his life.

His best friend Jack is divorced, with a kid and a career on the skids. Meanwhile Miles’s mom has suffered a stroke that’s left her wheelchair-bound and desperately wanting to go live with her sister in Wisconsin.

They trio set off, along with mom’s pot-smoking Filipina caretaker Joy and her high-spirited Yorkie, on an ill-advised road trip from San Diego to Oregon’s Willamette Valley, where Miles is master of ceremonies of the International Pinot Noir Festival.

Along the way they stop in Santa Barbara’s Wine County, revisiting the Hitching Post (where his mom drinks my favorite Alma Rosa Chardonnay) and catching up with Miles’ old girlfriend Maya and the Foxen Winery tasting room along the way.

Pickett knows the landscape well, witnessing firsthand the impact that Sideways has had on the local wine regions since he first began visiting Santa Barbara County in 1990 on a series of golf trips to escape his life in Los Angeles.

Rex Pickett on the set of Sideways

Rex Pickett on the set of Sideways


“When I wrote Sideways I was broke, I was nothing, I had nothing. I should have just killed myself,” he says.

The new book, Vertical, “goes to a deeper place than Sideways, there’s no question about it. But you have to also understand too, the truth of the matter is I had no one looking over my shoulder with Sideways, so I could just let it all hang out. I knew that Sideways has millions of fans. I get it every day, even seven years later. It’s huge that thing and can you imagine, you feel a certain responsibility, and you feel that you owe a debt in a way to the characters. But if you embark on a sequel thinking about that, you are going to end up with some low common denominator type of novel.”

At just over 400 pages and delving into some pretty intense subject matter (alcoholism, impotence and assisted suicide, to start), Vertical definitely doesn’t pander to the least common denominator.

The level of depth in the novel was quite intentional, but Pickett acknowledges he took a commercial risk.

“People who are reading it are really loving it; a lot of people are in tears actually.

I don’t think they expect the story to go where it goes, but it’s hard to get people to read a book that is 150,000 words, which is long for a book. Just 20-30 years ago that would have been considered an average size novel but by today’s standards it’s considered a long novel,” he says.

“I get asked a lot of questions about ‘what’s your next novel’ and I say there isn’t going to be one. … There’s a kind of way of reading which I term deep immersive reading, and it’s very simply you turn off your computer, you turn off your web-based phone and you turn off your TV and you sit in the chair and you read. And that kind of reading is unfortunately kind of going away,” says Pickett.

Disenchanted with people’s reading habits and the book business, Pickett says he is turning his energy to writing an HBO series set in the wine world of Napa Valley. “It’s about a famous wine critic who suffers from social anxiety disorder so acutely that he has to have a psychiatric service dog. So it’s funny, but it’s also going to be a real kind of insider look at the wine world and what it is all about.”

In addition, he is working on a theatrical play of Sideways, which he expects to premiere at the Ruskin Group Theatre Co. in Santa Monica in early 2012. “It’s a definite 100% go. It’s not like, ‘yeah I wrote a script and I got Johnny Depp attached.’ This is a definite go,” says Pickett, who just hired Amelia Mulkey to direct. “And here’s the wonderful thing; I’m so excited about the whole thing.”

Meanwhile he also has Vertical to market and will be signing books at this weekend’s 25th annual Santa Barbara Concours d’Elegance, to be held at the Santa Barbara Polo & Racquet Club.

“For me, Vertical is even more personal than Sideways. The overindulgence in wine which caught up with me during Sideways—and I went through a tough decade. Suddenly you have success, you don’t have kids you don’t have a wife and you have money. And worse, you wrote a book that deifies somebody who is passionate about wine and a lot of it, and suddenly everybody wants to give me wine and more wine and expensive wine. Pretty soon you become like Miles in Vertical. For me the most powerful thing is when he does sober up, it becomes a very raw emotional journey with him and his mother. … These books are very personal to me.”

For more information about Rex Pickett and Vertical visit

Author’s Note: If Pickett looks anything like his author photo, he is probably the only person in Hollywood history to have a fatter, less handsome version of himself in his movie doppelganger. Not that I don’t love Paul Giamatti, but I look forward to seeing who they cast in the play.



« »

Browse similar topics:

Web Exclusives, Wineries

Related Posts