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

Posted by Rex Pickett
Richard "RB" Botto Richard "RB" Botto
This is part II of the exclusive six part series: Rex Pickett – My Life on Spec: The Writing of Sideways. New postings will be made every Monday and Thursday through December 22nd. Don't forget to check out the foreword to this series and Part I.
Click here to purchase the sequel to Sideways, Vertical. Only $10.20 from Amazon. Check out Sideways as well if you haven't read that yet. Both make excellent stocking stuffers for the "Sidways" fan in your life.


Every creative knows what it's like to be in the zone. For an actor, every nuance of the performance is clicking. For a writer the mind is working faster than the hands can keep pace. For a director, every scene comes together in perfect symphony. All actions are done by and through the self. It's the purest form of artistry – a pristine sheet of freshly fallen snow.

But eventually, you have to release your art into the wild. Fear and doubt pay a visit - Turn your snow yellow.

When we last left Rex, he was full of confidence, locked and loaded, blasting through "Two Guys on Wine." In the second part of our exclusive six part series, Rex faces unpaid bills, doubt, a slightly shifty producer (man, is that an oxymoron), fear, his agent, a very old answering machine, doubt, and his ex-wife – whose opinion he fears.


-- RB

100 pages into the writing I was once again faced with my inability to pay the rent. A woman friend who worked in the wine business came over to share a bottle of something special she had purloined from the wine store and, I learned later, to seduce me. My head was so wrapped up in Two Guys on Wine that I was oblivious of the seduction part as I no doubt prattled on to her what I was working on with great enthusiasm. She was enthused by my, well, enthusiasm. I did something I swore I would never do - but I was so desperate! - I gave her those first 100 pages to read with an ulterior motive brewing unspoken in my head.

She read them, then returned a few days later and told me how much she liked what she'd read, how eager she was to see how it was all going to play out. I had her where I wanted her, so I played my joker in a desperate move: "Sharon" - not her real name - "For $5,000 I'll give you 25% of everything I make off this book, including film, TV, toys, sequel, everything." Sharon, who had a rich boyfriend, was taken aback. I repeated my proposal with greater urgency. She saw that I was serious and said she would think about it.

The next day I received an e-mail saying she wasn't interested in investing. I was bummed. (PS: that decision ended up costing her a healthy return on her potential investment.) In dire financial straits, I gathered up all my prized first editions - the hardest being my collection of the Collected Works of C.G. Jung (all 20 volumes; all first editions; all with their original dust jackets in perfect condition) -- and drove my cache off to a bookseller of rare and collectible books in Beverly Hills. It was heartbreaking to peddle these books that I had had for years, that meant so much to me, but I had no choice. I remember walking away with a check for $1,200 for books I'm sure the proprietor resold for quadruple that.

A tad deflated, but not discouraged, I returned with alacrity to the writing of Two Guys on Wine, the rent paid for another month and some modest provisions in the larder. Even though Sharon didn't invest $5,000 in the book, her words of encouragement re-galvanized me. Six weeks of exhilarating writing later I was finished.

The hard part was facing what I had wrought. I remember when I had come to the end I was monumentally depressed. I had laughed, and sometimes cried, with this book, and I didn't want that joyousness to end. I didn't want my trip with Jack to the Santa Ynez Valley to ever end. But, clich'es being clich'es, like all good things, they must, willy-nilly, come to an end. But I couldn't look at it. I thought it would suck, that I would fly into a rage and rip it up. I think a lot of artists feel this way after finishing a project, creating something new and unique, sucking the marrow of their own brains. It's not easy to go to that personal place and strip-mine that private part of your soul, but it's much harder to face it when it's done. The gestation and birthing can be, as it was in my case, exulting. Realizing that it might have been born with two heads and a heart condition is another whole other terrifying animal.

I took a few days off and tried to prepare myself to read my second novel Two Guys on Wine. Impatience to see what it was I had created, however, took precedent over doubt and anxiety and I sat down and read through it in one sitting. I remember being surprised at how fast it read, how much like a screenplay - I would get criticized for this later by the many publishers who rejected it - it felt. It was very dialogue- and character-driven and I liked the propulsive force of it. I noted where I could change, or amplify, on some things, but basically I just wanted to make a second pass to clean it up and not mess with it too much, for fear that I would diminish that proverbial lightning I believed I had captured in the bottle. Leave it alone as much as possible was my mantra for the rewrite.

I made another pass, which only took me a few weeks, then stood back and took a deep breath. The material was so raw and personal and, at times, even puerile, I criticized myself, that I was afraid to show it to my agent. So, I called Michael London, a former Fox executive now cooling his heels in his beachside home on Pacific Coast Highway and trying to claw his way back into the business. Michael drove over to my house in his BMW 733i and parked it behind my '91 Honda Accord. I handed him my manuscript - this was the day before e-mail and attached files. He glanced at the cover. It was a blank page. "What's the title?" he asked.

"Oh," I said. I took the manuscript from him and scrawled on the cover page with a Sharpie: Two Guys on Wine.

He looked at it. "I like it," he said.

"I'm not interested in any constructive criticism at this point," I admonished him. "I'm only interested in whether you think I should give it to my agent."

"Okay," he said, then roared off in his automotive leviathan.

I figured Michael - who didn't have much going on - would take a week to read it. He was accustomed to making the hard phone calls and, if he didn't like it, he would tell me straight up. Because he had a better sense of the pulse of the industry, if he didn't deem it commercial, I would probably trust his judgment, not give it to my agent and just park it and admit to myself that I was all wrong. Or rewrite it. If he outright hated it I would probably have buried it.

Two days later, Michael called and said he was in the neighborhood, could he come by? Sure. Bring my manuscript over in the Beemer, tell me how much you despised it! A few minutes later, Michael showed on my front porch holding the now dog-eared manuscript of Two Guys on Wine. He thrust it out at me and said, "Give it to your agent."


"It's great, Rex. I read it in one sitting and was blown away. Funny, moving. I had my wife Lynn read it just to make sure, and she loved it. Give it to Jess." And then he was gone.

As he purred off in his 733i, I almost shouted - my mind still obsessing about my overdue rent, the various creditors hounding me - "I'll option it to you for $500!"

I returned inside, a glow coming over me that I had been validated by someone other than a girlfriend wanting to appease me, or a parent hoping I would get a real job, or a friend praying I might pass his script or book to my agent with a ringing endorsement.

The following Monday I called Jess, my book-to-film agent at Endeavor, and told him Michael - whom he knew - had read my latest and that I was alerting him to its arrival. He said he looked forward to reading it, commiserated briefly about the continuing failure to sell La Purisima, then rang off.

A couple weeks passed and I didn't hear anything, and I started to grow anxious. Michael's endorsement was one thing - and with it came ulterior motives, of course - but Jess's was another. He was a living, working, real film agent and if he didn't want to go out with it, the book would probably have died there. To say I was eager to hear from him would be a gross understatement. There was nothing I could do. I didn't want to read it again and make changes for fear that I would start hacking into it with a complete loss of perspective and destroy what was fresh about it. I didn't have any money, so, naturally, there was no woman in my life to take my mind off of the waiting on the word from Jess. Besides, who wants to date a broke 40-year-old writer? A writer manqu'e, no less! So, it was just me and the daily gnawing of my own gray matter.

Between week two and week three of waiting I started to grow really apprehensive. He must loathe it! He's preparing to dump me! Why else would it take this long? I started to scout tall buildings with open rooftop access. I paced my two-bedroom house talking out loud to the walls. When my landlord came and pounded on my door to collect the overdue rent I defenestrated out the back window. The Saturday tastings at Epicurus were my only sanctuary, my only respite from a life seriously hanging in the balance, fingertips on the friable precipice. I didn't even care that I hadn't been with a woman in over a year.

Three weeks in I returned from a trim at Supercuts, looking like an FBI agent on a hangover, and noticed that my ancient answering machine's digital readout read "1." I figured it was this indefatigable creditor who had been badgering me for months and, as I played it back, I had my finger poised over the delete button ready to erase it. It was Jess. I don't remember his exact words, but he apologized for not getting back to me sooner, said he was vacationing -- Vacationing? What's that? -- in upstate New York, that he was 100 pages into the book and "loving it so far." Because I'm a half-glass empty self-lacerating kind of guy, I naturally focused on my negative interpretations of his brief message, reminded of a former, specious, agent who used to say: "Halfway through and loving it." And then nothing after that.

I speculated, I cogitated, I meditated, and, when I grew claustrophobic, I ambulated. The next day Jess called again. I was in the house when he phoned, but I didn't pick up. I didn't have Caller ID back in those days and answering any call could be dangerous to my sanity -- what little remained. It was Jess calling to say he was now 200 pages in to my 300-page manuscript. Again, I don't recall his exact words, but he was now really getting excited, really loving it. This on top of his first, somewhat cryptic, message had me excited.

I went to bed and fell into a disquieting sleep. The next day I came back from whatever I was doing - re-selling movie tickets I got for free off my WGA membership card probably - and there was another message. Again, it was Jess. The message was long, very long, so long that it caused my tape to run out. I have the tape saved somewhere, but I remember him rambling on and on, in a very excitable tone, raving about the book. It was alternately funny, page-turning, heartbreaking ... he was positively breathless with praise. I don't recall a single criticism. All I remember was his unbridled excitement, his eagerness to show it to the world. When the message was over I nearly fell to the floor, weeping. That's how much his words meant to me. That's how desperate I was for any semblance of good news.

When Jess returned from his vacation he drove over to my humble rent-controlled house in Santa Monica. In a breezy, insouciant mood, he was attired in flip-flops and shorts, very un-agent-like. With him he toted one of those portable wine coolers with a bottle of Byron sparkling wine I had given him a few years back to hold on to when there was something to celebrate. I had forgotten all about it, but he hadn't. (It's the same champagne that Jack crassly opens in the car with Miles as they leave the former's fianc'ee's house.) We uncorked and sipped while Jess went over the manuscript with me. He had very little editorial criticism. Afterward, he took me to a local Italian restaurant and we enjoyed a great meal on his dime. I hadn't eaten out in ages. I was almost beginning to feel human again, not having remembered the last time I had dine in a restaurant.

I was so psyched that Jess - and Michael - were excited and were strategizing on how best to go out with my little Two Guys on Wine. Over dinner, Jess confided that the one thing he didn't like about the book was the title. He complained it sounded too much like a non-fiction travelogue through wine country. A few days later, as I was reading through the opening chapter and making little changes, a title change omnipresent on my mind, I came across a moment where Jack accuses Miles of being sideways - obscure British slang for "inebriated." Sideways! I loved it. Jess immediately loved it. Michael loved it; then, later, would grandstandingly take credit for coming up with it himself! Producers.

New title on board, I made another, quick pass through the manuscript. Because I now had Jess's validation, I wanted my ex-wife's, Barbara. We had made two indie features in the '80s, and though they didn't really advance our careers, I still respected her judgment. She was my story editor par excellence back in those salad days - and a good one; she knew how to talk to writers; she knew how to extract the best from a writer -- a rare, and vanishing, skill in Hollywood. I called her -- she was newly married now -- and told her what was happening with Sideways, brought her up to date on Jess's and Michael's exuberant response, and asked if she would read it and weigh in before I made one final pass. I really wanted her feedback and... validation. Before Jess, every script I had written had gone through her before we went out with it, and I suppose a big part of me still wanted her input before I put the finishing touches to my book in advance of our "going wide" to both film and publishing. Excitement was high.

Several days after I gave her the manuscript, she called. She hated it. She disputes this today, but the truth is, she... hated it! I don't remember what she said exactly, but it was something to the effect of: "Burn it."


In Part III of Stage 32's exclusive series, Rex, confidence shattered, contemplates taking his ex-wife's advice or trusting his own instincts. Just when the haze begins to rise, his agent makes a stunning announcement.

VerticalPart III will be posted Monday, December 12th. 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. Don't forget to check out the first novel, Sideways. Both will make great holiday gifts for any "Sideways" fan.
Part III: My Life on Spec: The Writing of Sideways
Part I: My Life on Spec: The Writing of Sideways
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