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Of the major shifts in the wine world over the last decade, the Sideways phenomenon ranks near the top, alongside the Gary Vaynerchuk effect.  Released in 2004, the Sideways film is without doubt the most influential wine-related movie ever — grossing over $250 million and recipient of over 350 awards including an Academy Award.

Photo credit: Jake Trott (photo from RexPickett.com)

Though the originator of the wine-soaked adventures of Miles and Jack rarely receives as much credit as the actors, director, and producer of the Sideways film, Rex Pickett — author of the Sideways book, from which the film was adapted — arguably moved the Pinot needle more than any one person.

Those unfamiliar with the Sideways back story might believe that the man who created the Sideways phenomenon became fabulously wealthy as a result of the book and movie.  Not even close.  The trials and tribulations Rex Pickett faced on the road to getting Sideways published, and the film adaption, would have broke most people — a hard earned and costly education to be sure.  (Rex shares the Sideways back story in a six-part series, plus postscript, published at Stage 32 — My Life on Spec: The Writing of Sideways.  A fascinating read.)

Later this evening, Rex will be the featured guest on #WineChat — the weekly virtual wine discussion that takes place every Wednesday via Twitter — to discuss Sideways and his newest novel, Vertical, that continues the journey of Miles and Jack.

As a prelude to Wine Chat tonight, I had the chance to ask Rex a few questions that may need more than 140 characters to answer…

DWYL:  Thank you, Rex, for taking time out to field a few questions prior to Wine Chat.  Before we get in to Sideways, Vertical, and writing, I have to ask about your love of books.  Anyone who has the mental wherewithal to read all 20 volumes of the Collected Works of Swiss psychologist C.G. Jung is a (very) serious reader.   I winced when I read that you had to sell your collection of Jung’s Collected Works (1st ed., all 20 volumes) to pay rent pre-Sideways.  I imagine that was difficult to say the least.  Now that you are in a different financial position, have you repurchased the Collected Works for your library?

I’ve re-purchased most of them, but not all.  I realized that I would probably not go back to them again.  In truth, I’m in the process of getting rid of my precious book collection because they’re an albatross around my neck every time I move.

DWYL:  Sideways has been a cash-generating machine for those involved with the film, Pinot producers, straphangers, and many businesses and wineries in Santa Barbara County.  I read somewhere that you earned about $400,000 from Sideways.  Considering that Sideways (the movie) grossed over $250 million and won over 350 awards — including an Academy Award for Best Adapted Screenplay — one could make a reasonable argument that everyone even remotely related to Sideways monetized in a big way but you (and perhaps Merlot producers).  If the $400,000 figure is even close to right, this seems a paltry sum for the person responsible for creating the Sideways phenomenon.  Though money is not why you wrote Sideways, you no doubt learned many valuable financial lessons.  Did this experience change how you have positioned Vertical (the book and a potential film adaptation) to be financially rewarded commiserate with your artistic contribution?
RP:  This is a great question and it, unfortunately, evokes so many of my failings as a business person it makes me see red (and not green!).  Yes, many people monetizedSideways to the tune of millions, tens of millions in some cases, and I didn’t.  Not even close.  I made a lot of mistakes.  I wish I had discovered social media — and I’m not a Luddite — and its power 7 years ago.  Wish I had built a Web site as a merchandising center.  Wish I had hired PR peeople to get me out there more.  So many things I could have done that others should have been dong for me, but weren’t.  It’s sad really.  I just wanted to be a content guy and I figured my agents and others would monetize my success for me.  But, it’s not that easy, it doesn’t happen like that.  When you have an out-of-the-box success like Sideways you have to be smart about your choices, what you decide to write next, all kinds of things.  Because you might not have the opportunity to have those chocies again.
DWYL:  On your blog you write about the importance of deep immersive reading and your sense of guilt over the fact that you write for a living but now have difficulty reading them guilt that you do make time to read them. Though I don’t write for a living, I do love books and share that guilt with all the unopened classics on my bookshelf (as to most all readers).  What was the last piece of literature that you surrendered the time to immerse yourself in? And, who are the authors that you still need to read?
RP:  I feel the need to read so many authors:  Roberto Bolano’s massive 2666.  I’m currently trying to read Haruki Murakami’s 1984 but, sadly, I’m finding it a tough go for a host of reasons.  In fact Murakami’s latest, his magnum opus at nearly 1,000 pps., represents everything that is wrong with the way I read today.  Tethered to the Internet, it’s difficult to shut everything off and spend two hours a night with this book — which is what you need to do in order to have it yield its riches — and do this every night for two weeks or longer until finished.  I miss that rewarding experience.  Other than that, I read a friend’s mystery novel and a book on biodynamic viticulture by wine writer friend Katherine Cole in order to blurb it.  I’ve read so many books in my life, and there’re still so many out there to read.  Problem is, I spend all day writing and it’s difficult for me to shut everything down and open a book.  And they keep coming, like a tsunami, b/c of the ease in which the Internet makes it to write and print books.  I don’t own a Kindle or iPad or other tablet, and the reason is I don’t think I’ll read anymore on them.  I’m afraid I’ll stop to obsessively check E-mail, Tweet and looks at Twitter.

DWYL:  Many Sideways fans are waiting for the sequel, however, based on your Stage 32 Postscript it doesn’t sound like a Vertical film will happen in the near-term. Any hope a film based on Vertical will be made any time soon?

RP:  I think I answered the above pretty thoroughly on Stage 32.  I just don’t think Alexander [Payne] wants to do it.  And if he doesn’t want to do it it probably won’t happen despite the huge fan base.  Link your readers to that postscript for the detailed answer.  And with The Descendants having a success he has the power to stop it from happening with another director.  

DWYL:  Many bloggers today (the ones I know anyway) harbor visions of making the jump from online hobby blogging to paid print journalist. Any advice/lessons learned that you can share with those that may want to write professionally one day?

RP:  Since there must be a billion — literally — blogs out there I don’t see any future in blogging, which the Internet has unleashed on the world as the journal that everyone can write.  How does one find their way to the really good blogs and then stay with them?  I think there has to be some kind of winnowing process like there was 30 years ago — for books, movies, etc. — but I don’t think it’s going to happen.  I’d like to give advice, and I do, on this subject, but I’m very circumspect about the future of writing when, it seems, everyone is, and now can be, a writer.  All I can say is that there’s always going to be the need for great writing.  What form it’s going to take, I don’t know.  I’m blogging about this on Huffington Post right now — first entry to appear today.  I blog about it, but people are so inundated with blogs they’re not reading anymore.  I do believe in my heart that storytellling is innate to all of us human beings and that that’s not going to go away.  I would certainly not write long novels anymore.  If that’s any help.  I would recognize that audio/visual is the future and think about telling stories visually more than just as literary fiction, which I think is going the way of spear-making, sad to say.  It’s tough out there with books today b/c there are literally now million.

DWYL:  Given your busy schedule and the number of projects you have going — the Sideways play, The Nose, fending off nubile women, and writing — how do you recharge?

RP:  I try to work out at the gym.  Sometimes I’ll take off and go to the Santa Ynez Valley and play golf — but not very often.  I don’t really have an outlet for recharging these days.  I go at it from the moment I wake up.  
DWYL:  Sideways is credited with significantly moving the popularity needle of Pinot Noir while at the same time contributing to Merlot’s slump.  By most (all) measures, Sideways was a game-changer for the Santa Barbara wine region.  Do you foresee Vertical having a similar impact the Willamette Valley in a similar way?
RP:  If there were a film it could, but not unless it’s a film.  People aren’t aware of my sequel, which is why I’ve finally taken to social media to get the message out.  And it’s a long book, too … so, no, I don’t think the book will have that impact.  I don’t think books possess the power anymore to have that impact the way a movie does.  E.g., I don’t think Under the Tuscan Sun, as a book, would send people traipsing to Italy the way it did 15 years ago.  
DWYL:  Because of the success of Sideways you’ve been afforded some privileged access to people and places that few others are afforded.    Can you give us an example of some of this privileged access?  And, what access is still eluding you?
RP:  Well, it’s true I’m invited to some very high-end wine events, but I mostly turn them down.  Having written a novel that was made into a successful movie maybe gave me some access to the entertainment world, but it didn’t help me get a feature film I want to direct — I directed two indie features in the ’80s — off the ground.  Let’s put it this way:  Sideways gets me in doors I couldn’t get past before, but it’s no guarantee that someone is going to hire me for a writing job, or give me $3 million to make an indie feature.  And, let’s face it, every year there’s a new crop of hotshots.  Although, admittedly, Sideways has endured. 

DWYL:  You are currently working with Leverage Management, the production company behind HBO series like Boardwalk Empire, on a wine-related series — ostensibly to be titled ‘The Nose.‘  Can you provide any additional insights in to the series — when we might expect to see such a series, share any plot focus areas, etc.?

RP:  It is about a famous, influential wine critic and a young Internet upstart, but my models for the characters are very different than those two.  The series is currently in development, like many series.  And that’s about all I can about it now. 

Thank you, Rex, for taking time to share your thoughts on Sideways, Vertical and writing – looking forward to Wine Chat tonight.

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