Just about every wine lover has heard of the film Sideways, and most assume that the author of the novel on which it’s based – Rex Pickett – must be living in a Hollywood mansion from all the dough he brought in once the movie hit the big time, and made Pinot Noir cool again.

Wrong, Jack – Pickett got a paltry five grand for the novel. But with a sequel (Vertical) now in print, a successful play based on Sideways, and plans to head down to South America to write a third installment, Rex is slowly getting even with the wine and publishing worlds. I caught up with Pickett to get his take on Vertical, what it’s like to write about sex head-on in the sometimes-stodgy world of wine, and why he’s escaping to Chile to complete his tale of the drinking exploits of iconic characters Miles and Jack…

Playboy.com: Almost every wine lover knows Sideways. They probably assume that you were well compensated and that you can easily reproduce a sequel and it would be made to a movie. But that isn’t the reality.

*Rex Pickett: * I tell this story a lot: my ex-wife, who won an Oscar for a best live action film for a short that I wrote and now teaches at NYU graduate film writing and directing, told me to burn Sideways. Nobody wanted it. In fact the publishing world hated it so much that my agent pulled it after 15 submissions and said “This is a face plant, Rex!” It took Alexander Payne a year to read the novel and then option it. Artisan Entertainment (Blaire Witch Project) was flush with money in 2000, they green lit it as a $10 million film, so it was front page that “Payne Goes Sideways!” My publishing agent goes nuts, he goes back to the publishing world and they still turn it down. Over 100 rejection letters in, we more or less forced it onto the publisher for $5000. One of the worst decisions I have ever made. If I had not taken the $5000 and waited for the movie to come out, I would have been offered over a million dollars for the book.

Playboy.com: In a similar way, with Vertical as a sequel, you have had kind of the same path.

Rex Pickett: I’m sure people are thinking, “he is writing the Sideways sequel, he has a $2 million contract.” But that is not the truth. It was a real struggle. When Sideways hit I was hot and everybody wanted me to write TV and do screenwriting. My publisher said I needed to write another novel. I remember saying to him that I wanted to write a sequel and my agent said “you don’t want to do that because they own the film rights”. They read a screenplay I wrote in the early ‘90s called The Road Back, about a mother and son on a road trip. So that is the part that ultimately got into Vertical. I was writing that without a contract, then I find out that the publishers didn’t want a sequel and that they didn’t like the ending and wouldn’t publish it with that ending. The good news is that I got it published privately and we just won the gold medal for the independent publishers award for fiction. It was a long haul that was not fun.

Playboy.com: Let’s talk about Vertical as a successor to Sideways. There is a lot of sex in there (even at the International Pinot Noir Conference where Miles speaks… has anyone ever had sex at IPNC?)…

Rex Pickett: There is a resurgence of prudery out there. If you go back to the 60’s and you take people like William Boroughs or Lady Chatterley’s Lover. We fought these battles in the Supreme Court years ago. When I showed the novel around initially to some people and they were going “Oh God, Rex, whatever” so I scaled it back a little. In terms of page count I’m going to go out on a limb and say there may be no more than 5-7 pages of sex but the pages that are there are not only graphic but are written in first person, so it hits a lot of people like “whoa!” I think that writing in 1st person, if you have a sex scene or something about too much drinking or whatever, it seems to be amplified or becomes more palpable because you personalized it. It is a little bit like you have a laser into my soul. I think that is one of the things that people admire about what came across in the movie and play, that I write from a very personal place. But if you add it up, Tropic of Cancer makes me look like Dr. Seuss! I write from a personal place and I write from a very honest place and I don’t pull punches.

As far as wine goes, I’ll go on record in saying is that the real story inside the wine world is that these people really drink a lot. I don’t judge them, but that is a fact and they may be a bit uncomfortable that I key in on it.

Playboy.com: What’s the deal with Sideways the play?

Rex Pickett: The Ruskin Group Theater is a 55 seat house next to the Santa Monica Airport. About one and half years ago there was event called Pinot Days, so I went and everyone was pouring Pinot. Somebody from the theater came to the event and ran into me and said have you ever thought about doing a play. I said I hadn’t but I met with them and they really wanted to based on the book, not the movie. I loved their passion, I started in filmmaking and love it and a play is similar. We are in our 18th sold out week and I demanded that we would have wine tasting for free with proper stemware, every night we had a different wine maker come down and pour for free and pour, liberally, high end Pinot Noir. We poured by the bottle between $40-50k bottles of wine for free. Now we are having trouble because we are in our 3rd extension. You could come down and drink and break even on the cost of the play and the free wine. That has been wonderful, to see them enjoy wine, take the wine into the theater and watch it. We are going to do a road show, I just signed with one of the biggest theatrical touring agents in the world. We are hoping to do it in the bay area, with our current cast.

Playboy.com: People are still talking about the Sideways Effect, with Pinot Nor sales increasing and Merlot sales declining due to the movie. Do you every get shit from Merlot producers? You went on the record as saying that Merlot needed a correction from where it was in the 80’s. You have been unapologetic about the impact the film had on Merlot.

Rex Pickett:I get a few questions from interviews and people at the theater. When I wrote the line I wasn’t thinking that this was going to be a movie or have any impact and when I wrote it back in the late 80’s merlot was a bit of a joke. I don’t know that the line is even going to make it in the movie or that Paul Giamatti is going to utter it with even more venom! In Bordeaux, Merlot is wonderful, in Napa where they mass market it now you have a $5 plonk that deserves to be vilified. Pinot Noir has just soared, but we are not starting see cheaper Pinots on the market and now they are going to do the same thing with Pinot.

Playboy.com: Are you shelving Miles and Jack now that you have Vertical finished?

Rex Pickett: At the end of Vertical Miles falls in love with a Spanish girl. So now I’m heading to Chile for 4 months as an artist resident to research the part three of the trilogy. It has been a wonderful thing. There are no restrictions, I’ll write whatever I want to write. I feel like taking the characters somewhere different. With Sideways, wine is the back drop for me but the marketing has made it the forefront. But it is really about two guys, in their mid 40s, and failure. Vertical is really about success and where success leaves you. But I have had people tell me because of the way the play is written that I have written an epic love story. So I think that part 3 is going to be a love story.