I met Rex Pickett, the author of the novel Sideways that inspired the beloved film, at a showing of Sideways: the Play, which is currently playing at the Ruskin Group Theatre in Santa Monica, CA.

We spoke over a glass of Pinot (yes, the wine comes with your ticket, which is already surprisingly affordable for live theater), and he was very gracious with his time, even though he was no doubt answering the same questions about the movie that he’s fielded dozens of times. Most of all, he came across as an uncensored, uncompromising artist with no fear of burning any bridges — he shoots from the hip because he has to — that’s just his personality and he doesn’t compromise.

I knew I had to get him on my blog.

He doesn’t pull punches in the interview below, especially when firing back at me. (For the record, I won’t be asking him to endorse my book any time soon!)

DAN CALVISI: What’s your background as a writer?

REX PICKETT: I started writing when I was 18. I wrote poetry — self-published two collections — wrote experimental, post-modern, Peter Handke-derivative fiction, made a couple experimental films, then wrote and directed two independent feature films, California Without End and From Hollywood to Deadwood. It was the analog days and each film took four years out of my life. Both were sold – the first to Bavarian Radio Television, the second to Island Pictures. Island butchered FHTD and it was released to poor notices.

So, I didn’t start writing screenplays, it just came about as a desire to make films. In the mid-’90s I wearied of spec screenwriting and decided that because I felt like I had more to offer, prose-wise, than other screenwriters — where you really don’t have to be a skilled prose writer — I decided to write a novel to differentiate myself from the masses writing screenplays. That’s when I truly found my voice.

Screenplays are all written in third person. A novel can be, too, but mine are all written in first person. A great screenplay is like imagining a novel and then adapting it without having written the novel. But a novel is a full unfurling of one’s sails. It’s everything. I’ve said many times: it’s way easier to write a mediocre or bad screenplay than it is to write a mediocre or bad novel. That’s why so many people opt to write screenplays rather than novels. That, and, of course, to cash in.

The marketing aspect is the same: you go out to agents, and anyone else in a position of power to peddle, or sell, your work.

I want to make one film in the digital day. My two features (I directed) were made in the analog days, and it was brutal, barbarous, horrible.

What’s your experience with screenwriting? Do you have that favorite unsold spec sitting in a drawer somewhere that you hope to get made someday?

My experience with screenwriting is twofold: when I write it for myself I love it. When I write scripts for hire, or get involved in development, I loathe it. Most people in development in Hollywood are utterly inept as interlocutors when it comes to talking to writers. I’ve only met two people in my entire career who knew how to talk, and give constructive advice, to a writer. One was an erstwhile publishing agent, and he had a nervous breakdown and left the business. The other was my ex-wife and she told me to burn “Sideways” because she feared it would embarrass me. (I almost did!) Last add on writing for hire: As one very famous film producer once said to me congenially over coffee: when we hire you we feel like we own you, and we will screw you up and down if we want to.

Yes, I have that one favorite unsold spec. It’s called “Repairman.” I just optioned it, and this time I’m the one attached to direct. I want to make one film in the digital day. My two features were made in the analog days, and it was brutal, barbarous, horrible.

Most people wouldn’t think the writer of a smart character piece like Sideways would have a high concept Hollywood popcorn movie in him, but maybe you do? Would you write something like The Matrix or Transformers? Does Channing Tatum drink Pinot or Merlot?

I’ve had low moments where I’ve tried to write so-called “High Concept” movies, but I’ve always failed. Anything that doesn’t smack of verisimilitude doesn’t work for me. Besides, if you write a high concept movie you might make millions, but, more than likely, you’re going to end up on the receiving end of some crass moron like Adam Sandler or Brett Ratner or Judd Apatow controlling your work.

What led up to writing Sideways and what was the initial response after being published?

I refer your readers to my lengthy 15,000 word blog/essay in 7 parts titled My Life on Spec: the Writing of Sideways.

If you write a high concept movie you might make millions, but, more than likely, you’re going to end up on the receiving end of some crass moron like Adam Sandler or Brett Ratner or Judd Apatow controlling your work.

What made you sell the rights to Fox Searchlight and Alexander Payne? Did you have any say on aspects of the film?

I would have sold the rights to the head of the Sinaloa cartel I was so broke. When Payne read it — see above blog for detailed insight — I was ecstatic. Fox Searchlight? Are you kidding me? They’re the creme-de-la-creme of the film specialty world. Payne showed me every draft of the script. He’s that kind of a guy. He’s interested in your input, but he controls every aspect of his movies.

One of the first things Alexander Payne said to me when we met in person was: “You know what I liked about your novel so much? Your characters are so fucking pathetic!”

How do you like the film and do you feel like it does justice to your book?

I truly love the film, but it’s a slightly different view, shall we say, on my novel. One of the first things Alexander Payne said to me when we met in person was: “You know what I liked about your novel so much? Your characters are so fucking pathetic!” Now, bear in mind, Sideways the novel was written in first person from the standpoint of Miles (Paul Giamatti), so I took it kind of personal because, well, the book is very personal. I didn’t think I was “pathetic.” Going through a rough patch, perhaps, but not pathetic.

It definitely does justice to the book. For one thing, it stays in the first person. We never go where Miles doesn’t go, which Payne had the luxury to do, which I didn’t in the novel, of course. But, he didn’t. He also employed the chapter structure of the novel in the movie: Sunday, Monday, Tuesday, etc. … recreating them with inter-titles. A different take on my book can be seen in my Sideways: the Play. There, Miles is not quite so hangdog as played by Giamatti. He’s a funnier guy in his self-deprecation and ostensible rudderlessness. Jack is not the remorseless, sex-crazed Terminator in the play that he is in the movie. He has more heart, more soul, more depth. So do the women. But, other than that, and other than Sandra Oh changing her tertiary character and giving her an interracial kid (which makes Jack even more pathetic) and Payne making Miles a middle school English teacher, it’s very faithful to my novel.

What was the film’s impact on your career?

Not as great as some people might have imagined. Certainly doors opened. But a lot of people rushed in to take credit for things they shouldn’t have, especially Michael London, the producer, who lied about so many things in the press it wasn’t funny. He lied that he got the book to Payne — no, that was my agent who had a nervous breakdown, Jess Taylor. He lied that he developed the novel with me. That infuriates me. He had absolutely nothing to do with the development of the novel. He lied that the title “Sideways” was his idea. And that’s only the lies I know about. After the movie he got a $200 million hedge fund, started a mini-major studio and blew it all on a string of unreleasable films. Hell, the merchants and winemakers and restaurateurs of the Santa Ynez Valley — where the film was shot — made way more than I did. Fox Searchlight didn’t invite me to half the awards ceremonies. I got a ticket for the Oscars at the last minute, but didn’t get to sit with the creatives. I sat high in the rafters.

The whole experience was bittersweet. Sure, I’m the guy who created the universe of this now iconic film, but I was thrown under the bus by so many people it wasn’t funny. When you have a success like Sideways people get really hoggy when it comes to credits and money. Sure, I got a publishing deal after that and offers to do scripts, but so many people made so much more off of something that I (see my blog piece) spent 10 years, more or less, creating, that it still stings to see them wallowing in their millions.

Is “Sideways: the Play” closer to the book and in what ways?

Sideways: the Play (L.A. Weekly review) is the book, my version of the book (see above answer). There are scenes from the book that are not in the movie. For legal reasons I couldn’t use anything in the movie that wasn’t in the book, but there was nothing that I wanted to use from the movie that wasn’t in the book. The play goes emotionally deeper than the movie. And the ending, right out of the book, is more redemptive. Emotion and sentiment are out of Payne’s comfort zone, so he avoided them wherever possible. Film critic Peter Rainer, in praising Sideways, said, after giving a thumbnail on Payne’s first three features, “In ‘Sideways’ Payne turned in his sarcasm for a soul.” I would rephrase that: “In ‘Sideways’ Payne turned in Payne for Rex Pickett.” And that was the greatest honor Payne gave to the movie: he honored the soul of the book, except where he didn’t in a few places. He often held back. That’s his aesthetic sensibility, not mine. I have no compunctions about going to the personal. I’m fearless in that way. The personal makes Payne queasy sometimes, but Sideways was so personal he couldn’t totally ignore it. And, as a result, it’s his most personal, and successful, film.

I once said to a young D-girl at a major studio who asked me to write a treatment for an idea I had pitched: “I don’t’ write treatments,” I explained. “How come?” she asked. “Because writing treatments is like dry-humping a blow-up doll,” I replied. That pretty much ended that meeting.

How do you find working in theater vs. film or novels? Did you edit the manuscript right up to opening night or was it locked early?

I love working in theater. It’s been the greatest, most rewarding creative experience in my life. They’re all totally different. Writing a novel takes a long time, it’s a private experience, and it can be excruciating to hold all those words in your head for so many months, years. Film is exhilarating to make, but once you get into the editing room — or on Final Cut Pro in your office as the case may be today — you’re stuck with what you’ve shot. Theater is a living, cyclonic thing. Once it’s cast, it’s like a runaway train without brakes. Very maddening. Very palpable in every single aspect. But when it works it’s more thrilling than a film because the reaction is immediate; again, distinctly palpable. Film is 2-D, novels are 1-D and 4-D (the reader’s imagination), but plays are 3-D all the way. The membranes to ones sensitivity meter are parchment paper-thin.

The cast is great. How’d you find them?

This is Equity waiver. We went out with “breakdowns,” got submissions, held auditions for the ones we liked, then held callbacks. It was brutal. The who’s who don’t come out for theater that pays nothing. These are real actors who do it for the art, not the money, not that they don’t want money. And, frankly, we lucked out.

Can you discuss the ending of the play/book and the ending of the movie. Maya showing up at Jack’s wedding is a far cry from a voice message left on Miles’ machine and him knocking on her door before we cut to black.

Yes, it is a far cry. In the first three drafts of Payne/Taylor’s adaptation of my novel the movie ended on the voice message on Miles’s answering machine from Maya. Alexander said to me very early on: “There’s no way I can do your ending because it’s too Hollywood.” Okay, cool. But ending on Maya’s voice on Miles’s answering machine and going to black, it’s neither fish nor fowl I told him. In the fourth, and final, draft of the script he had Miles driving up in the rain and knocking on the door. I.e., he sort of met the novel halfway. Here’s the deal: Payne has said in many interviews that he doesn’t like sentimentality. I don’t either when it’s slathered on gratuitously like margarine in a stupid Nora Ephron movie. But if you earn it, why not play that card? And there’s no question after what Miles has been through in that week before Jack’s wedding in the Santa Ynez Valley that he needs a little hope for something, one little scintilla of redemption. I’m happy Payne put that knock-on-the-door ending in instead of ending on the answering machine, but it’s still chicken shit as far as I’m concerned. Maya doesn’t come to the wedding to forgive him so they can walk off together in the sunset. That’s bullshit. She comes to the wedding to tell him in person that she read his novel and thought it was brilliant and that she saw in him, in reading it, something greater than the person who cavorted transgressively with his reckless friend Jack the previous week.

Certainly doors opened. But a lot of people rushed in to take credit for things they shouldn’t have, especially Michael London, the producer, who lied about so many things in the press it wasn’t funny.

When did you decide to write Vertical?

This is a long story that I blogged about in four blogs on Huffington Post Books blog. In short, I signed with Knopf to novelize a script I had written in the early ’90s titled “The Road Back.” It was about a young music video director based on David Fincher — whom I worked with as a writer on Alien III — whose mother has had a stroke and is wheelchair-dependent, and who, through a series of circumstances, ends up on the road with her and her dog and her caretaker on a road trip from San Diego to Wisconsin. The script was much-admired, optioned for 4 years, never made. I had trouble novelizing it and Knopf treated me like the scum of the earth, so I got out of my contract and decided to turn it into the Sideways sequel with Miles, 7 years later and now a success, on the road to the International Pinot Noir Celebration in the Willamette Valley of Oregon with his mother, her dog, a caretaker and … Jack. En route to, eventually Wisconsin. That worked. It just won the 2012 Gold Medal for Fiction from the Independent Publishers Book Awards.

Miles is NOT pretentious. I take umbrage at that. Pretentious means to pretend to be something you’re not. Miles is clearly a wordsmith par excellence and he takes a wry, even droll, pride in his use of lexicological arcana.



Vertical seems to be quite autobiographical. Which elements came from your life and did you need to change Miles’ character to adjust to where you were at in your life? The book opens with you dumping a spit bucket on your head and having a threeway with two beautiful sommeliers. Please tell me this is true to life!

Everything — and I mean almost everything — in Vertical is a fictionalized version of reality; or, more accurately, emotional reality. What I went through with my mother is all true, albeit fictionalized in a road trip. My friendship with Jack (a real person) sort of became that. And my life as a success instead of a failure became that, too. Dumping a spit bucket on my head is not true, but it metaphorically felt like it was. No comment on the bedroom scene with the two sommeliers.

Will there be a movie of Vertical?

This is answered extensively in a blog I just wrote for my site: here. Excerpt:

Fox Searchlight owns the film and TV rights to Miles and Jack, the iconic duo in Sideways. I own the literary, and other, rights. Anything I write with a Miles and Jack – and Maya and anybody else from the movie — in it they control in perpetuity (i.e., forever), and can do whatever they want. I’m powerless. If they don’t want to make a movie they can elect to sit on the project and do nothing with it; i.e., I don’t have the right to shop it somewhere else. That’s the deal… And, you know what? I could get a call tomorrow from someone very important. “Rex. We’re making Vertical.” Hollywood is that crazy.

How did you learn so damn much about wine?! Was there a wine master whom you killed in his sleep, once you had surpassed him in knowledge? C’mon, now’s your chance to unburden yourself. 😉

I learned everything about wine from Julian Davies, a friend who worked in a now defunct little wine store called Epicurus, and the great wine writer Jancis Robinson, who wrote “The Oxford Companion to Wine” — a veritable, nonpareil, encyclopedia on wine.

Miles’ voice is incredibly literary; lots of references to obscure writers and ten-dollar words. (He uses “ignominy” a lot, fer criminy’s sake.) Did this voice come naturally to you or did you have to do a lot of research to write such an over-educated, pretentious type? (i.e., Are you Ivy league educated or just faking it?)

Miles’s voice comes naturally to me. I love words. And, if you read between the lines, he’s clearly making fun of himself. And Miles is NOT pretentious. I take umbrage at that. Pretentious means to pretend to be something you’re not. Miles is clearly a wordsmith par excellence and he takes a wry, even droll, pride in his use of lexicological arcana. Am I “Ivy League educated or just faking it?” That’s an asinine remark. Why, do you think Ivy League-educated people have it over someone who went to the University of California at San Diego? I fake nothing.

On that note, Miles ALSO drops lots of F bombs and has a very crass side. What made you give him this kind of duality and contradiction?

Miles doesn’t have a crass side! Are you kidding me? He’s an ethicist at heart. And why is using “fuck” and “pussy” words a sign of crass? Is D.H. Lawrence crass? We fought these battles — some in the Supreme Court — 50 years ago. And why use the word “F-bomb”? Are you afraid to say “fuck” after the Supreme Court ruled it was okay in a trial on whether William Burroughs’s Naked Lunch should be published or not? I see no “duality” or “contradiction” in Miles’s character from the standpoint that he’s a self-professed autodidact and intellectual and the fact that he likes to pepper his speech with “fuck” and “pussy” and “shit” and “motherfucker.”

I let ideas build up in me until, like fruit drooping from the tree, they’re ready to burst. Then, and only then, I start. And I have to have an ending; it’s a desideratum for me…I don’t care how I get there, how much I detour or deviate, I want that ending.

How do you structure your narratives before you write? Do you believe in classical 4-Act “Hollywood” structure?

I absolutely loathe the 3-Act structure formula of Syd Field and Robert McKee and John Truby and all those failed writer-turned-screenwriting guru guys. Loathe them to no end. I’ve never read a book on writing and I never will. Linda King did a nice book titled: And the Oscar Goes To … It was a detailed analysis of the screenplays of Sideways, Crash and Shakespeare in Love. Okay, I didn’t write the script, but the structure is pretty much the same as the novel. My God, the things that woman came up that never, in a million years, went through my head when I was writing the novel Sideways. Never, not once, did I think: okay here I’ve got to turn the screw a little tighter. It just came instinctually. You can’t teach, or learn, that. I can’t imagine for the life of me reading that book and then taking it to the blank page and employing all the little plot twists and turns, the detailed analysis, into the actual writing of a script or a novel. It actually made me laugh to read such a detailed, broken down into component parts analysis. What’s the point? It can’t be interesting for a non-writer. And for a writer it’s worthless.

To answer your question, I don’t structure my narratives. I start with character — me and my friend Roy (i.e., Miles and Jack) — then I move to setting, then I start to think story out of character. Again, see lengthy blog My Life on Spec … as it goes into detail on my writing process. I take a lot from real life. Real life gives me real character which, in turn, gives me real story. Narrative comes last. I let ideas build up in me until, like fruit drooping from the tree, they’re ready to burst. Then, and only then, I start. And I have to have an ending; it’s a desideratum for me. I always want that destination. I don’t care how I get there, how much I detour or deviate, I want that ending.

Writers who map out scripts on 3X5 cards bemuse me. How can you possibly know what a character is going to do before he/she even speaks? That’s why I refuse, mostly, to write treatments. I once said to a young D-girl at a major studio who asked me to write a treatment for an idea I had pitched: “I don’t’ write treatments,” I explained. “How come?” she asked. “Because writing treatments is like dry-humping a blow-up doll,” I replied. That pretty much ended that meeting. So many scripts that I read — and I rarely read them anymore — read like they were mapped out on 3X5 cards or someone had just taken a McKee seminar. I hate formula. But formula sells, so what can I say? Maybe that’s the reason “Sideways” is so fondly remembered today, even though it’s been more than seven years since it was released. It’s anti-formula. In every way: character (who verge on the unlikable — a no-no in Hollywood); story (wine-tasting? really?), and so on.

Miles is one of the most real characters in recent cinema precisely because he’s negative and depressed and, in some peoples’ eyes, a loser. THAT’S screenwriting 101A.

Sideways the movie has an unconventional protagonist arc, in that Miles basically gets his ass kicked for the whole movie, culminating in the ultimate indignity of drinking his most prized wine out of a paper cup in a burger joint, and then there’s a tiny hint of redemption in the final scene with the phone message. I’ve heard from a few people over the years who hate the movie because they felt he was such a negative, depressed loser; but for me, that was the point, and I loved it! Thoughts, anecdotes, tribunals?

I don’t view Miles (me) as a loser. And what’s wrong with depression? What’s so great about happiness? Our culture sells us happiness so we buy the psychopharmaceuticals to falsely achieve it. I write my best when I’m depressed. And what’s wrong with being negative? The world is not a meritocracy and 99% of the people in this world have every right to BE negative. I’m circumspect of positive, upbeat people. They’re insincere, disingenuous, specious.

Look, semi-facetiousness aside: In order to find redemption, you have to begin with its opposite. This is the crux of all good writing, and the problem with all bad writing: having the ability to create a seemingly unlikable, negative, depressed, dyspeptic, self-deprecating, failure of a character and transform him. Miles is one of the most real characters in recent cinema precisely because he’s negative and depressed and, in some peoples’ eyes, a loser. THAT’S screenwriting 101A.

Sideways at its core, to me at least, is a buddy story. Two best friends have their friendship challenged by extreme situations, with escalating stakes until our hero must make a final moral choice to either support or abandon his weaker friend. Is that how you would characterize it and what were other dramatic elements that you consciously constructed before you wrote vs. ones that flowed organically as you were writing it?

Yes, ultimately it’s a deeply abiding story about friendship, which is why women like it even more than men, if you can believe that. Jack’s loyalty to Miles, despite the former’s transgressions, is really singular. And Miles’s vulnerability is something women would like to see more of in men, but don’t. In film after film, men are invincible protagonists — their flaws are phony bs that we’ve seen a million times before. They rarely show any emotion or sensitivity.

I talk in my book about sympathy for our protagonist, and I say how the lead actor can get away with a lot more on screen than on the page. For example, Paul Giamatti in the movie steals all of that money from his mother’s sock drawer ($800?). Yes, she just embarrassed him in front of his friend in regards to his divorce and lack of income, but, still…stealing from your senile old mother?! I would contend that if this were a spec script from an unknown, many readers would have written him off right then and there. What makes us still want to follow this jerk?

I’ve had to answer this question a million times, so here goes again: Payne saw the characters as pathetic. So, of course, stealing money from his mother, in the movie, is pathetic. But in the book, Miles is late on his rent. His mother lives in an upper middle-class house overlooking the ocean in Montecito and is not some middle-class woman in an apartment in Ventura. In the movie, Miles also has a job; in the book he doesn’t. So, of course it’s pathetic in the movie because Miles, who has a job, gets his middle-class mother drunk and then steals from her. In the book, Miles who can’t pay his rent, takes laundered money shielded from the IRS from his well-to-do mother and then … get this!: Jack gives him the money to pay it back as a gesture of kindness, showing his heart, the day before the wedding. Showing heart is not one of Payne’s fortes. And, yet, in the movie, people still love Miles because everyone can relate to his wanting to be something, aspiring to something greater and then getting smote down by a seemingly unfair world. That’s how most people feel in life that I run across.

Who are your favorite wine makers in the Santa Ynez area? My wife and I love Daniel Gehrs and Scott Cellars, both in downtown Los Olivos. (Thanks to you, we do our “Sideways” trip usually once per year, and we even stay in the Day’s “Windmill” Inn because we’re nerds.)

Foxen Winery. Brewer-Clifton. Cebada (just coming out). Sunstone.

What’s your best advice to up and coming screenwriters?

Ask yourself: How low can you go and still turn on your laptop? If you come to Hollywood to make money you’ve already sown the seed of failure. It’s a life, not an avocation. Read. Read great literature. See great movies. Steep yourself in literature and film. Then write. Gird your loins for rejection. Recognize that getting an agent means little. Recognize that even your friends are wrong. Find someone whom you trust for objective feedback. Be very careful whom you choose. Keep writing. Don’t wait on anything. Another aphorism I coined: In Hollywood, between enthusiasm and money lays the Grand Canyon. Don’t believe anything until you see a check or cameras downloaded off the grip truck. Keep writing. Producers are the biggest liars in Hollywood, not agents. Be wary of anyone calling themselves a producer. Most of them are charlatans. Most will rip you off if they get a chance. Keep writing. Know your world. Know your characters. Don’t take screenwriting seminars. Be original; find, work indefatigably for, an original voice.

Advice on getting a manager or agent?

The most boring, banal question a professional writer gets asked. My advice? Try not to get one. Let them want you.

In 5 years the skill-set to read “War and Peace” will have completely vanished. I see no future in long form writing. Period.

E-books are the hot way now for a new author to build an audience. Do you care if someone reads your book on a Kindle vs. a paper copy? Do you think new authors should self-publish or still pursue a publisher?

This would require a long answer. Deep immersive reading is being destroyed by the Internet and e-Readers where E-mails pop up on the screen while you’re in the middle of a novel. In 5 years the skill-set to read “War and Peace” will have completely vanished. I see no future in long form writing. Period.

You seem to have a pretty active social media presence. Do you enjoy it and any tips for how to best use Facebook, Twitter, et al?

This would also be a long answer. I hate Facebook. It’s worthless as a promotional tool, great if you want to tell your friends and family what you had for dinner last night. Twitter I love. My advice? Be personal, be real, don’t over-promote. [Rex’s Twitter and his website]

What are your favorite movies in terms of the writing?

The list is endless: Towne’s Chinatown and The Last Detail are brilliant scripts. So is Wilder’s/Brackett’s/Marshman’s Sunset Blvd. Many, many others. The list just goes on and on. And sometimes it’s not just the script. There’s virtually no script for Fellini’s 8 1/2, but it’s one of the unqualified, paramount masterpieces of cinema. Ditto for his La Dolce Vita. So, it’s not always about the script

Anything else you want to add?

To all the fans of Sideways out there: it was not the Immaculate Conception. It was based on a novel, a novel that someone, unwittingly, suffered his whole life to write

THANK YOU REX and good luck with your future projects!



Good luck and happy writing,

Dan Calvisi

“A brilliant example of what every aspiring screenwriter needs to know about the art of writing screenplays. A must read for serious screenwriters.”

-J. Stephen Maunder, writer/director