Part I: My Life on Spec: The Writing of Sideways

Part I: My Life on Spec: The Writing of Sideways

Part I: My Life on Spec: The Writing of Sideways

Rex Pickett
Rex Pickett
11 years ago

My Life on Spec: The Writing of Sideways

In 1990 my life was in the veritable Dixie Dumpster. My second indie feature, From Hollywood to Deadwood, had been butchered by its distributor and released to critical opprobrium. My wonderful wife and I split up for reasons that would make this story way too long. Worse, my mother was felled by a massive stroke that left her wheelchair-dependent with full left-side paralysis. My younger brother, out of ostensible altruism, brought her back home after a three-month stay in the hospital -- during which time she suffered a heart attack that she barely survived -- and, in the course of a little over two years, gutted her nearly half a million in savings. At the behest of my older brother, I sub-rented my rent-controlled house in Santa Monica and moved back to San Diego to assume control of my mother’s care and attempt to get her to agree to go into assisted-living. It wasn’t easy. Nothing with her ever was.

In the course of living with my mother – who, when I took over, could only afford part-time care – and trying to move her, she came down with congestive heart failure at 4:00 a.m. Had I been sleeping soundly, she would have died. Five paramedics, in a frantic, at times barbaric, episode, revived her and she was hospitalized for another two months. After her another stint in the hospital, this time seven weeks, I moved her into an assisted-living facility in Carlsbad, just north of San Diego. But, I was so broke, I couldn’t afford to move back to Santa Monica. I had hit rock bottom financially.

I stayed on at my mother’s seaside condominium while trying to unload it, but the real estate market was seriously depressed and property wasn’t moving. It took a year and a half to sell it, during which time I learned that my agent had died of AIDS, my wife served me with divorce papers and informed me that she was remarrying, and I awoke to the fact that my modest trust fund was, because of my younger brother’s mismanagement of my mother’s savings, gone. I was destitute, agent-less, divorced, jobless, and, approaching 40, unemployable. No wonder I started experiencing panic attacks, one of which landed me in the ER of the V.A. Hospital in La Jolla. To say I was walking on eggshells back in those days would be an understatement. I was an emotional wreck. I thought it was all over. I’ve since joked many times that if I could have afforded a gun I would have shot myself.

Backing up just a bit. When my second indie feature failed in ’90 and my marriage crumbled, I took up the game of golf again in an effort to escape the quotidian failures of my life. I hated playing in the L.A. area because it was crowded and the play slow. I started to journey two hours north to Santa Barbara to play a great public course routed along the ocean. I became friendly with some of the locals. They kept urging me to drive an additional 50 miles to play La Purisima (literally translated, “the pure one”) Golf Course. At first I resisted – it meant a total of 300 miles of driving back in those days – but then one day, as I like to reminisce, I went over the hill.

The 101 Freeway north of Santa Barbara turns very rural. Just like Miles and Jack in the movie Sideways, you transit through a short tunnel and then climb the gently-sloping Santa Ynez Mountains. A few miles later you reach the crest. As far as the eye can see is the Santa Ynez Valley with its untrammeled vistas of rich farmland, acres of vineyards and rolling hillsides emblazoned with wildflowers.

La Purisima Golf Course is a dream come true for a golfer. It’s a gorgeous piece of property, unsullied by cookie-cutter real estate bordering the fairways. When I first started making the trek, I would go up and return the same day, but the 300 miles was back-breaking, so, even though I was dead broke back in those days, I started to stay overnight, play a second round in the morning, then return to my dreary, depressing life in L.A. Just like Miles and Jack in the movie, I checked into the Windmill (now the Day’s) Inn. It was only $29.99 back then. After a hot shower, I needed a place to eat. The desk clerk recommended the Hitching Post, a short half-mile walk. At first I was a little creeped out by its dark wood-framed, windowless façade, fatalistically imagining a biker bar where no doubt I would be knifed to death if I so much as looked at someone the wrong way – a fate that might have been welcomed back in those dark, bleak times.

The Hitching Post was quiet on those midweek days in the mid ‘90s. The first thing I noticed, other than the fact that it was definitely not a biker bar, was that they made their own wine. A Pinot Noir. Hmm. I had just started to get into wine tasting at a local wine emporium in Santa Monica where, for a mere $4, you could while away a Saturday afternoon with some nice – well, often supercilious – company. And, for some reason, my palate had gravitated to Pinot as my grape variety of choice. So here I would sit all alone at the bar at the Hitching Post – try that today! – after a great round of golf, freshly showered, burger and fries and a salad, a glass of Pinot, and… a gorgeous waitress named Renee. Without my knowing it, unwittingly, Sideways was starting to form in the intracranial wonderland of my imagination. Funds allowing, I kept returning again and again to this magical place that seemingly few people knew about -- if you were traveling up the 101 and missed the turnoff for Highways 246 or 154 you would unwittingly pass an entire wine region, an entire microcosm, if you will. One day I had “gone over the hill,” stayed and, in my mind’s eye, never left.

In the mid-‘90s I wrote a mystery novel titled La Purisima. It got me a publishing agent, but the novel didn’t sell. Rejection letter after rejection letter slowly trickled into my mailbox, a veritable slow morphine drip for any writer. During that time, my publishing agent, Jess Taylor, moved out from New York to L.A. to become the book-to-film agent at the powerful Endeavor Agency. La Purisima was handed off to another agent at Curtis Brown, LTD. Though my novel wasn’t selling, I had gone from virtually nowhere to now having two agents, one on each coast. I was marginally beginning to feel better about my life, even if my brother, my (now) ex-wife, and her sister, were keeping me afloat, and growing tired of the last-minute phone calls for hand-outs.

I was so enamored of the Santa Ynez Valley I started inviting friends up. One mid-week sojourn was with my good friend Roy Gittens who had been employed as an electrician on my second indie feature film, From Hollywood to Deadwood. Unlike me (Miles), Roy (Jack) is an outgoing, gregarious guy, catnip to the ladies, and with a laugh that is basso profundo infectious. By now I was coming up to the Santa Ynez Valley as much for the wine tasting experience – tasting rooms were free back then! – as I was for the golf. On this particular trip, Roy and I – this was back in ’96 – careered from tasting room to tasting room, getting more and more looped. With my occupationally sardonic sense of humor I soon had Roy in stitches. At one point in our shambolic sojourn, Roy, face flushed red, said, “El Lumbre” – his sobriquet for me in those days – “why don’t you write this as a screenplay?” Hmm. We riffed endlessly on the potential movie idea as we navigated the sinuous country roads from Byron Winery to Foxen Winery, to… We joked about potential titles until finally I alighted on one that had Roy snapping his fingers in approbation: Two Guys on Wine.

We returned to Santa Monica and I immediately set out to write Two Guys on Wine as a screenplay. I wrote it in a matter of two or three weeks. I hated it. Something just didn’t click with it. The tone, something. I so hated it that I didn’t show it to my few trusted friends or my agent, fearing the latter would dump me or, at best, distance me, for having given birth to such a piece of garbage. That’s how insecure I was in those lean and self-flagellating days. Shortly thereafter, with nothing else to do but write and contemplate suicide, I was playing with a short story titled The Bullpen. It was about one of the Saturday afternoon wine tastings where I now was an habitué. I don’t remember why, but I just instinctually wrote it in the first person from the standpoint of the character in the Two Guys on Wine screenplay, Miles. The story came in a rush, as most of my writing does once the idea and characters have taken root in my protean imagination.

But then something happened that was game-changing. When I got to the end of The Bullpen, I literally stood up from my desk, a flare going off in my head: Two Guys on Wine will be a novel, written in the first-person from the standpoint of one Miles Raymond. It will open at Epicurus Wine Emporium. As the tasting that day deteriorates into a brawl, Jack will show up, rescue Miles from the melee, and then the two of them will head off to the Santa Ynez Valley for a week of wine tasting before Jack is to be married to a society girl. In that one fulguration of the imagination I had the whole novel adumbrated in my head. I had my opening, I had my ending – I consider these to be the essential components before I write anything – and I had that first-person narrator’s voice in Miles, which was so freeing for me as a writer. Screenplays are so constrained by their montage-like nature, and they have little room, because of their form, for creating a character’s interior life. But a novel written in first-person obliterates those constraints and liberates the writer to do almost anything, go almost anywhere he chooses.

Excited, galvanized, I was off and running! I wrote the first draft of Two Guys on Wine (soon to be re-titled Sideways) in nine weeks. As I said, I had my opening, and I had my ending. And, I had the setting – and all the locations in it, which I could picture in my imagination from all the trips I had taken up there, as if I had been transported there at the blink of an eye. And I had Jack/Roy. I could literally hear his voice in my head. I knew exactly what he would say or do in any given situation. And I knew, before his marriage, his character was going to be up to no good. And I knew things were going to start getting real complicated at the Hitching Post and that the appearance of Renee (Maya) would kick the whole thing into high gear. It’s just such an ecstatic feeling to know exactly where you’re going with a story when you’re writing. But, to make it really work, to make it truly effloresce into a novel, I knew that they had to get into mischief, that things had to go wrong, that, as a writer, I had to box my characters into corners, send them down twisted roads to various cul-de-sacs and then figure out a way to rescue them if I was going to be able to go the distance that a novel requires. And I knew one thing more: if I was going to sell myself as Miles – the depressed, out-of-work screenwriter (in the book) who can’t sell his novel and who has to steal from his mother -- I had to lace it with humor. Without humor, it could easily turn into a depressing, stream-of-consciousness, solipsistic slog.

Every morning I couldn’t wait to get up and write. When I was done with the day’s writing I would feel both exhilarated and deflated. Do I really have to open the mail? Can’t I just live this fantasy forever and never have to deal with the realities of life, of showing it to anyone? While writing I was so inside the story and the characters it was the equivalent to a movie unspooling in my head. The writing was easy. Easy after a decade of financial deprivation and personal suffering and living a life I was now unwittingly writing about. Easy. Or so I thought…


In Part II of Stage 32's exclusive series, Rex, confidence brimming, writes Sideways. And then… doubt. Is it a publishable manuscript or a self indulgent piece of garbage? What will his agent think? And, maybe more importantly, what will his ex-wife think?

VerticalPart II will be posted Thursday, December 8th. In the meantime, we invite all Stage 32 members to leave comments on the series. Or ask Rex a question. He'd love to hear from you.


-- RB

Vertical, Rex Pickett's sequel to Sideways, is available now for only $10.20 in paperback and $7.69 for the Kindle edition. It would make a great holiday gift for any "Sideways" fan.

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About the Author

Rex Pickett

Rex Pickett

Director, Playwright, Screenwriter

I'm the author of "Sideways," the novel upon which the Oscar-winning Alexander Payne film was based. My new novel "Vertical" is the sequel and has been available for over a year now. I'm currently in NYC involved with casting my "Sideways" (the play). We had a phenomenal run at the tiny Ruskin Gr...

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