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Rex Pickett Interview by Rick Bleiweiss

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Rex Pickett Interview - Listen Now

RICK BLEIWEISS: Welcome to’s interview series. I’m Rick Bleiweiss, and today it’s my pleasure to be speaking with award-winning novelist Rex Pickett. Rex is the author of the acclaimed novel Sideways, which was the basis for a film directed by Alexander Payne, staring Paul Giamatti, Thomas Haden Church, Virginia Madsen, and Sandra Oh, which won an Academy Award for Best Adapted Screenplay. Rex adapted his novel Sideways for a Broadway play and his sequel novel Vertical, won the 2012 Gold Independent Publishers Book Award. He is also a screenwriter, most notably of the Oscar–winning My Mother Dreams the Satan’s Disciples in New York, and the director of two indie films; California without End and From Hollywood to Deadwood, which was theatrically released by MGM. Blackstone Audio is publishing the audio version of his latest book Vertical, narrated by Scott Brick, on March 15, 2013. Welcome, Rex. Thanks for joining us today. The New York Journal of Books says of Vertical, and I quote: “Rex Pickett shows that his gift for creating wildly funny scenes is quite intact. The book is laugh-out-loud funny.” Great quote. Vertical is the follow-up novel to the blockbuster Sideways and tracks the continuing story of Miles Raymond, and his buddy, Jack. When did you decide to write the sequel, and did you have a specific intent for it?

REX PICKETT: After Sideways, I did a deal with Knopf, the literary division of Random House, to novelize a screenplay I had written, called The Road Back, in the early nineties. The novel wasn’t working for me. Basically, it was a story of a young music video director whose mother had a stroke, and through a series of circumstances, ends up on the road with her. I had an epiphany to turn that into the Sideways sequel. I just went off in a completely different direction with the novel. Knopf wasn’t particularly happy that I was writing a sequel—for God knows what reason—but that’s the novel I wanted to write, so that’s ultimately what happened. It really goes back to 1993 with The Road Back—much admired, optioned for five years, never made, sort of a classic Hollywood story. Then, my agents, after Sideways, trying to capitalize on me, thought it would be a great idea to novelize that screenplay. I was very hesitant to do it. I didn’t want to rake over old bones. I tried, I tried. We did a deal. It didn’t work. Thus, the Miles mother story in Vertical had its genesis in a screenplay I wrote in 1993 called The Road Back.

RB: You know Sideways has become quite a brand. How did that evolve and what does that mean for the future?

RP: I didn’t have any control over it being a brand. When the movie came out, I suddenly realized that—first of all, it won over 350 awards—it was incredibly and immensely popular. I was just starry-eyed. Ten years prior to that, my life was in terrible shape. As time went by I realized that not only did the film have a huge impact in the wine world, but that it was a fondly remembered film. From time to time I would visit the setting of the film—the Santa Ynez Valley—and I would see how it had changed that area. I was there recently, and there’s this little tiny town, Los Olivos. When I  went there in the nineties it had three tasting rooms. Now, it has forty. It is basically a Sideways theme park, but it didn’t hit me full force until we did Sideways: The Play. It was just a lark. Someone approached me two years ago at a book signing and asked if I wanted to do Sideways: The Play in a fifty-seat theater. I was very hesitant. The bar was set very high, but I thought it’s under the radar, it would be an interesting way to do it, and we’d see what happened. Thus, non-equity, three performances a week, sold out for six months. It now goes to the La Jolla Playhouse with three-time Tony Award–winning director Des McAnuff—which has been publicized everywhere—and then to Broadway and the world. I was at the theater every night and it was just amazing. People remembered that film like it was yesterday, and I thought, “My gosh, these characters are universal. They’re archetypal. What they go through, it resonates on a level that is not ephemeral.” That’s when I realized this really is a brand. Now, I’m down here in Chile researching part three of a potential trilogy—as yet to be determined whether I’ll write it. The play is a big thing. The Sideways audience is colossal, the fan base is colossal, and the play is proving it, and hopefully it will continue doing it at the next level. So it’s really … I guess—I hate to use the word—“exploiting” it, but … I think the play gives them another way to experience those characters. You can only watch that DVD so many times, and I’ve met people who’ve seen it one hundred times. And it was electrifying, the play.

RB: How did the movie deal come about for Sideways? And how much involvement did you have in the making of the film?

RP: I’m going to give one quick answer. If you go to Stage32—the number thirty-two—.com, I wrote a 15,000-word blog—it’s in the deluxe edition of Vertical—but it’s a long story how it came about. I wrote it in the nineties, my then-agent was at Endeavor, which is now William Morris Endeavor, and we went to book publishing and film with it. Publishing hated it. We pulled it. Film didn’t get it. One of the submissions was to Alexander Payne’s agent down the hall, a guy named David Lonner. But it took Alexander Payne a year to read it—a year—and by then my agent had had a nervous breakdown. He left the business. My publishing agent had stopped submitting it. We’d all completely given up hope on it, and then out of the blue, a year later, Alexander Payne, through his agent, contacted me. I had gotten a new agent at Endeavor. We’d all given it up for dead.  It was after Payne’s second film, Election, and he was very hot in Hollywood. He had what we call “green lighting power,” and he just had stacks and stacks of manuscripts, because Alexander Payne tends to like to write from source material. An assistant for Payne, Brian Beery, was just reading through and—bear in mind, this was an unpublished novel—and he read it and gave it to Payne with a ringing endorsement. It was a year after it had been submitted to him. My agent had had a nervous breakdown, so he wasn’t even involved. Since then, certain people have taken credit for that, but really Jess Taylor is the one who was owed that submission. Michael London, the eventual producer of Sideways, has lied repeatedly to the press that he’s the one who got it to Payne. He’s the one who was the brain behind it. He’s even lied that he helped me write the novel. It’s unbelievable when you have a success how … but I don’t want to wax bitter here. I just love giving credit where credit is due. It’s amazing how a lot of people stepped in. I think one of the wonderful things about the play for me is when the movie came out, I pretty much got thrown under the bus. It was all about Michael London and Alexander Payne and the actors and everything else, and now with the play, the writer’s kind of king. It’s been a wonderful thing what these characters have endured, but it was a long process. Payne optioned the novel from me and he was going to make it his third feature, but as it turned out I get a call one day and he tells me he’s going to make another film called About  Schmidt with Jack Nicholson. So I had to wait another two years. It’s a long story, and I really do urge people to go to Stage32 online and click on blogs and go to December 2011—but everything that was involved in writing it and what led to it getting made and the aftermath.

RB: Well, I know I’m going to read it. Piqued my interest, that’s for sure. Rex, when did you begin writing and how did your career progress into writing full time?

RP: I started writing when I was seventeen years old, just writing poetry. I grew up middle class in a suburb in San Diego and kind of an alienating environment. Maybe I was just looking for some means of expression or something. Then I went to the University of California in San Diego, which was a hotbed of creative thinking, and I started reading a lot and seeing films—my background is both in literature and in film—and I met a lot of writers and I was making films. So I was writing, making films, met a woman, we got married, we made two feature films together. But even filmmaking for me was more a means to get my writing, my ideas, out and both films were finished—ten years out of my life. Both were sold. Second one was theatrically released. It didn’t do well. Island Pictures butchered it. I went back to writing. My career’s had fits and starts. I self-published two books of poetry. I started writing avant-garde fiction. Of course, no one would read that. I made two feature films. Then I went back to screenwriting. I’ve sold screenplays. Then I started writing novels. I wrote one before Sideways and it didn’t get published—thus Miles, who can’t publish his novel—and now I’m writing a play. So I guess I’ve kind of done it all. I phased through all writing mediums.

RB: In Sideways and Vertical, the characters and stories seem to be inspired by your personal life. Is that true of only that series or does that pervade most of what you write? And is it comfortable or uncomfortable writing about your life and your own experiences?

RP: Well, that’s a big question. There’s no question that Sideways is very personal. It’s a mixture of the personal and the fictional. I mean I’ve never had a naked man chase me out of a house down the street, but a lot of the details about Miles’s personal life—being divorced and going through and trying to get his novel published—that was all what I was going through when I sat down to write it. Vertical is very personal because the mother story, which goes back to that screenplay The Road Back, dealt very much with my mother and her stroke and what I went through. So I’m always mixing the personal, but I fictionalize it because I’m not really interested in writing autobiography. I consider it to be narcissistic. I’d rather have the license to be able to fictionalize, especially for comic purposes. In Sideways, in that particular case when I wrote it, I said, “Okay, I’m in a very, very bad place in my life, but if I can make it funny and if I can find a narrative construct for it, which I did—the one week in the Santa Ynez Valley before a wedding—then I can bring in the personal.” In other words, the story becomes a delivery system for the personal if you follow that. Is it hard when I’m writing? It’s not hard. It’s easy for me to write it because I feel like I’m venting, I’m getting things out. What’s hard is when I go to the world. I mean my ex-wife, she’s the interim chair at the NYU film school. She has an Oscar for Best Live Action Short that I wrote the screenplay for, and she told me to burn Sideways. I was dating a girl and she read the novel, and I never heard from her again. It’s easy to write from the personal place. It’s hard to go out and get the reaction from it. Then, when you get validated, it’s all that much sweeter. I don’t write in any other way, but I think when you put yourself out there personally and you are rejected, the rejection is so much more hurtful than if you were to write for instance just a cop thriller or something. Because you took a greater risk to put yourself on the line there and you can come across as solipsistic and all these other things that people might say. However, when it does succeed, as Sideways did, the validation is way greater than if you’d written Paranormal 4.

RB: How did wine end up being a focal point in Sideways and Vertical? And how did you become interested in grape growing and wine, and choose to make it part of these books?

RP: Well, in the nineties, I always drank wine but really didn’t know what I was drinking and couldn’t really afford it. And in the nineties, after my second feature film, I had a divorce, Mom had a stroke—bad, bad, bad times—but in my neighborhood in Santa Monica there was a little wine store I used to go to. I was also going up to the Santa Ynez Valley, but mostly to play golf. I  realized this little wine store on Saturday, from three to five o’clock, had tastings. It was a small group of guys. It was only four dollars. I was broke at the time, and it was a social outlet for me. I was a very lonely person at that time, and so I started going there and these people started to lord their knowledge of wine over me and I don’t really like being in a situation where people can put me down for my lack of knowledge of something. So I started reading about wine, continuing to go, continuing to listen, and realized—I’m sounding like Miles now—but there’s like a bottomless ocean of mystery in the world of wine. There are many grapes, many regions. Every year is different. And that really spoke to me. The art of winemaking is analogous really to art. These people really are artists. They deal with difficult circumstances. They make creative choices in the vineyard and in the barrel room. Then they don’t really even know what that final product is going to be. It’s very similar to writing art. So that really called to me. It became both a witting and unwitting metaphor for Miles and art and things and life, but it wasn’t in the forefront and I didn’t think about that metaphor because if you think about metaphors they’re dead. Metaphors become alive when you don’t think about them. But of course when the film came out, the wine world went crazy. Young people rushed to wine stores because Miles rhapsodizes and lyricizes about this one grape variety, and as a result the wine world put Sideways in the forefront. I didn’t. They did. I’ll take the credit, along with Alexander Payne and the movie. It was part of my life and I was writing from a personal place. I never had any idea that it was going to turn into the phenomenon that it did, that the wine business would double in five years, largely attributable to the movie, from what I can understand. That pinot noir would go from 1 percent to 8 percent of the red wine market, almost totally attributable to the movie.

RB: Rex, I know. I was living in New York City at the time the film came out, and after the film hit, I would go into restaurants and they’d be carrying pinot noir for the first time on their menus.

RP: Well, without question. I mean the statistics are … there are some that are quantifiable and some that aren’t. But the wine business before Sideways internationally was forty billion. Two years later, it was ninety billion. You can’t quantify it all with it. There’s inflation and other factors. There’s another statistic that the number-one adult beverage of choice every year in this country in, I don’t know, a Reuters poll or something, was always beer. The year after Sideways it was wine and it’s been wine every year since. So it made wine drinking hip. It made people want to look into wine and say, “Wow. There’s something more here,” because Miles saw something more in there. Maybe they thought that it would be easier to get the women of their dreams because it seems like that’s the only way Miles can communicate his thoughts and feelings to the lovely Virginia Madsen. I don’t know. There are a lot of factors, but it definitely made wine drinking hip. Now, I thought it would be ephemeral—last a couple years and then people would be on to something else—but it isn’t. It is officially—I know this is at the risk of immodesty—it is a cult film. You go up to the Santa Ynez Valley on any given weekend—this film came out over eight years ago—and it is basically the Sideways theme park. It is ridiculous. But I think it’s not just the wine though. I think the characters speak to a lot of people. Jack and Miles are sort of archetypal opposites. You have the introverted thinking type and you have the extroverted feeling type, and they represent both sides of the psyche. Not just male but also female psyches. I think that it resonates with people over a longer period of time. So it’s not just the wine and the high jinks and the comedy. It’s the humanism and the verisimilitude of those characters, which has helped it endure as a film.

RB: I know you’re speaking to us from Chile and that your website and your blog, have you there. I believe you’re working on a book in the Sideways series. Other than the play, is this the next project we’re going to see from you and what brought you to Chile?

RP: I started taking control of my destiny because I got tired of people making money off of me.  I got on Twitter and other things and I met a gentleman on Twitter, and he’s some sort of culture rep, agent, or whatever, and he said, “Have you ever thought about writing a part three?” I said, “Not really.” And he said, “Well, what if Miles and Jack came to Chile?” I said, “Well, you know, there’s an old saying in Hollywood. Everyone has their price.” One thing led to another and I thought this would be an incredible adventure. And, of course Vertical ends with Miles apparently going off to a Spanish-speaking land—Spain or wherever—and I did it so it would be unconditional. There would be no influence peddling. Basically, ProChile, which is their governmental organization that sponsors things in this country—business ventures—and Wines of Chile, which represents a number of wineries down here, they’re funding a research trip. Imagine it as a country saying you’re an artist in residence in Chile. Chile is an antipodean mirror opposite of Oregon and California, so it has the potential to be a great wine region. It’s in a very nascent state right now. And so I’ve been here two and a half months. In fact, you’re talking to me five and a half hours before I’m headed back to work on the play. So to answer your question, that’s why I’m down here. I can choose to write or not write this third part here. The play opens on July 21. That’s a contractual date. I need to now throw my focus into the play and then at that point I’ll see where my head is at and if there really is a novel down here.

RB: Rex, who or what has been your biggest influence over the years?

RP: Oh, gosh. When I went to the University of California, San Diego, in La Jolla—it’s a great university—my eyes were opened to—they brought a lot of people out from the East Coast—but definitely Manny Farber, who died a couple years ago. He was a film critic and a painter and he had a film class. I was seeing films that just were nothing like I had seen as a high school teenager. So Manny Farber was a huge influence.  I read a lot and saw a lot of films, but when I was nineteen years old, I dropped out of school, or took a couple quarters off, or whatever you want to call it, and I read the entire collected works of Carl Jung—all twenty volumes. Took me six months reading five hours a day and it really gave me a huge look into the world of the psyche, the soul, mythology, story. Jung predated Joseph Campbell, and, as we all know, Joseph Campbell is responsible for Star Wars, and we all know that Robert McKee, the screenwriting guru, takes everything from Joseph Campbell. Well, Campbell took it all from Jung with Jung’s blessing, while I read the original guy, C. G. Jung. So he had a huge influence on me, and then there are just many writers. I mean Raymond Chandler, is a mystery writer. I always liked his redemptive quality. I mean, Sideways is about a failure, but I had Miles in the end find some kind of redemption. I think Vertical is about success, but I had Miles find humility. And I don’t know what the third one would be, but I’m always looking for that and that’s what you get in these stories, these myths and folklore and fairytales and so on. So I would say Manny Farber, Carl Jung, those had huge early influences on me, and various people I would meet. I could rattle off numerous filmmakers, I could rattle off numerous novelists—definitely film and writers. And I always gravitated to the personal too, even back then. I liked Henry Miller back then. I mean, I realize now a lot of it was probably braggadocio but I liked it because he was coming from a personal place. As filmmakers, I like the more personal films. By Jean Eustache, The Mother and the Whore, a great French film made in 1973. I always kind of gravitated to that which cut deeply into the soul of human kind. I always related to that.

RB: Do you listen to audiobooks?

RP: I do. You and I talked and I said, “How’s that audio market out there?” And you said, “Well it’s kinda getting…it’s small, but it’s actually rising.” I realized maybe part of it is because when audiobooks first came out, you had to have eight CDs and put one in and out. But now it’s all digital and iPod and whatever else. The other day, I was with winemakers down here in Chile, and I met a guy who only listens to audiobooks. He’s constantly driving around—and he only listens to audio, but he says he can come home and I guess he takes the player out or something like that from his car and he can go to an eBook and it knows where he is on an eBook. I’m taking a flight, it’s a twelve, fourteen-hour flight to LA. I’m going to be listening to—you’re going to laugh at this—it might be Sideways and Scott Brick. The play is based on the novel, not the movie, for legal and creative reasons, and although I’ve already done the play, we’re having to redo it. So I need to kind of revisit some things because the Tony award-winning director, Des McAnuff, wants me to include some different scenes. We’re rewriting it, so … yes, I do listen to audiobooks. When I was talking to this guy who  doesn’t read books anymore; he’s only into audiobooks, it may save literature. I was fearful that reading was going the way of lacework. So the longwinded answer to your question is yes.

RB: Here at Downpour we’re going to be launching our own version of what you’re describing as the hybrid, where you can read the eBook or listen to the audiobook and they know where each other are and they highlight the words. We’re going to be launching that sometime in the next few months ourselves, and I’m looking forward to Sideways and Vertical being available in that format through us.

RP: Great. I mean it’s fantastic. Let’s face it, analogue books are probably going to ultimately be e and audio. Both. They both have this wonderful tie-in. I just got my first eReader,  and I put PDF files on it. When I’m doing rewrites of scripts, instead of using hard copy to the left of me, computer to the right, I actually use the eReader now. And I think it’s great.  Let’s face it. Paperbacks, five years from now, won’t exist. Hard copies may exist only because they still have a sentimental value or something, and autograph. I think the future’s probably totally e and audio. So I’m excited about this.

RB: The bottom line I think it is that the medium or carrier is less important than the content. So as long as we get people still consuming the content, that’s more important than how they do it.

RP: Well, I agree with you and I think the thing with audiobooks is I’m fearful that the kind of reading I did when I was young, which I called deep, immersive reading where you read two, three, four hours a day at a sitting. You know it’s getting harder and harder to turn off your computer and turn off your iPad and turn off your cell phone and turn off your TV and sit in a chair with the light on and read. I think that audio allows reading to be done in circumstances where you wouldn’t otherwise do it, like driving in your car for example. I think you’re doing a great service here. I think you’re keeping literature alive because people aren’t reading as much as they did back in the sixties and seventies. We risk losing an entire art form, especially the longer form like War and Peace. It takes a little bit of time to read that,  but people are listening to War and Peace on audio.

RB: I agree. Rex, I’d like to thank you very much for being here, actually being in Chile and talking to us today. We’re really excited about the audio version of Vertical. I’m also personally excited about the theatrical version of Sideways. I’m a huge theater fan and I intend to see it.  I think if there is a third book in the Sideways trilogy, I’m hoping it comes out sooner than later and I know it will be as great as the first two. So thank you again for joining us today.

RP: Thank you so much, Rick. It was a pleasure.

RB: Thank you for joining us for this interview with Rex Pickett. You can find Rex Pickett’s novels Sideways and Vertical at

This interview was recorded in January 2013.
Disclaimer: This audio and transcript have been edited slightly from the original recording for quality and readability.

While on research in Chile, award-winning author Rex Pickett talks with about his acclaimed novel Sideways and his award-winning sequel, Vertical. Rex gives the inside scoop on the Sideways movie deal, his Broadway adaptation of Sideways, and the huge fan response surrounding his works. He also shares his insights into the book industry, his enjoyment of audiobooks, and what he’s working on next. Get to know Rex Pickett in this entertaining interview conducted by Grammy-nominated producer Rick Bleiweiss, here on!


Sideways is the story of two friends, Miles and Jack, going away together for the last time to steep themselves in everything that makes it good to be young and single: pinot, putting, and prowling bars. In the week before Jack plans to marry, the pair heads out from Los Angeles to the Santa Ynez wine country. For Jack, the tasting tour is Seven Days to D-Day, his final stretch of freedom. For Miles—who has divorced his wife, is facing an uncertain career, and has lost his passion for living—the trip is a week-long opportunity to evaluate his past, his future, and himself.

A raucous and surprising novel filled with wonderful details about wine, Sideways is also a thought provoking and funny book about men, women, and human relationships.

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Sideways by Rex Pickett

Additional Titles by the Author/Narrator

  1. Sideways 3 Chile by Rex Pickett Sideways 3 Chile
  2. Vertical by Rex Pickett Vertical
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