Sideways author Rex Pickett: ‘Take risks. Be trailblazing’

Rex Pickett has achieved what most budding writers will only dream of: an agent, a publisher, a best-selling novel, a movie… He’s also pretty blunt when he describes the trials of being a writer. That combination makes for some incredible insight and no nonsense advice about what it takes to really make it.


Pickett is perhaps best known for his 2004 novel Sideways which, as well as being a success on the shelves, was picked up by director Alexander Payne and cast onto the silver screen. It went on to collect more than 350 major awards and a cult following that endures to this day.

The book itself is now part of a trilogy, and Sideways will be coming to London’s St James Theatre on May 31.

I asked Pickett about his path to success – and he didn’t pull any punches…

What was your first paid writing gig and how did you get it?

I wrote and directed an indie film titled From Hollywood To Deadwood. Before it sold to Island Pictures it screened at the Mill Valley Film Festival. The Daily Variety gave it a pretty rave review. I was contacted, via phone, by a guy who just identified himself as Grant Forsberg and said he worked for MixedBreed Films. At that time, with the imminent sale of my indie film I was getting a lot of those “fishing” kinds of calls. I blew it off.

Several weeks later, this Grant Forsberg left a second message on my answering machine (I rarely answered my phone back in those days because of ongoing problems with creditors) and went a little more into detail. He said he was the newly-named head of development for Kevin Bacon’s MixedBreed Films at (then) Columbia/TriStar. Well, that got my attention. I called him back. He said they were looking for a writer for a film for Kevin. Okay. They had read the review of my From Hollywood To Deadwood, noted that it was a mystery, and the idea they were developing was a mystery. They asked to read the script. I said, sure. I sent it.

A week later he called back and said they loved the script, would I like to come in and meet with them. So, I drove to Columbia Tri-Star (now Sony Pictures) in the Valley, went onto the lot, which is always exciting the first time for a writer (after a while it becomes synonymous with a queasy stomach and massive migraines) and met with Grant Forsberg and Kevin Bacon. They said they had picked my screenplay out of some 300 (all submitted by agents, by the way), explained that they had a two-year overhead deal with Columbia/TriStar. Okay. I’m listening.

So, they said they were developing a mystery where Kevin would play a detective and that maybe somehow his dog was his partner. My head kind of went back in that gesture where you’re sucking in your breath. Then, they said: “Do you have any ideas?” I said, “Yeah, how about the dog talks.” They looked at each other, kind of vaguely intrigued. Then, with perfect comic timing: “How about Kevin only barks?” There was a beat, then we all laughed. I said I would come up with someone and get back to them. Kevin asked me if I had an agent. I said I didn’t.

A few weeks later, Grant and I went in to see the head of Columbia/TriStar, a guy named Jeff Sagansky and one of the heads of development, a Kathy Lingg, I believe was her name. I pitched a mystery. Because Kevin had a two-year deal they practically had to greenlight projects to be written/developed in order to justify the money they were paying for the overhead of MixedBreed Films. After my pitch, Sagansky looked at Lingg, then turned to me and said, “Great! Do you have an agent?” I said no. He said, “Get one.”
Kevin must have put out the word because soon literary agents at his then Triad Agency were calling me. So, I got an agent, did a deal with Columbia/TriStar, I got into the WGA, and I was off.

The script was written, thrown on the pile, the agent I signed with unceremoniously dumped me. First hard lesson: when you’re hot, [don’t just] sign with anybody. You’re the boss. Agents are only as good as their clients. And he was just the first shark to smell blood, and I was too naive not to shop around.

I’ve read that your first novel, La Purisima, ‘didn’t sell’. Is that the case? If so, looking back, why do you think that was? Would you have approached that whole project any differently given the chance?

Yes, La Purisima didn’t sell. 80 rejection letters. I was told by my then publishing agent that it didn’t sell because they couldn’t figure out how to market a mystery with two central male characters in a market where 95% of all mysteries were read by women. That was the explanation I was given at the time.

I would not have approached the project any differently. I don’t write for a market. I don’t care what’s supposedly selling. I don’t operate with that mindset. That doesn’t mean I’m not aware of what’s going on in the world of film and literature and TV. I am. Keenly aware. But, I’m not about writing for a supposedly hot market (memoirs, I don’t know).

But, I’m not, for example, going to write a post- post-modernist novel that is half a million words long a la Infinite Jest or Roberto Bolano’s 2666. As much as I admire them for doing so. That would be suicide today and a waste of my time. I want to be read, but I don’t follow fashion. I’m an anomaly.

There’s a fine line between being commercial and marketable and being true to your voice, true to who you are as an artist.

You found big success with your second novel, Sideways, what was the difference there? How did you get that one off the ground?

I don’t know what the difference was. I was still refusing to follow any fashion. Looking back, I would say the fact that it was a comedy had a lot to do with it. La Purisima was a mystery in the vein of Raymond Chandler.

Sideways also had movie written all over it because it was written in a scene-and dialogue-driven style in the way that screenplays are composed. It was/is a romantic tragi-comedy, if you will, so maybe it hit more commercial buttons, I don’t know. I don’t think about stuff like that when I’m writing.

It also was more personal. It hit a nerve. Well, at least with Alexander Payne. Because, initially, no one wanted it. In fact, it was derided and reviled even worse than La Purisima when my agent went out with it. In fact, so derided that he pulled it from submission and begged me to rewrite it.

Actually, Payne’s assistant Brian Beery is owed the credit for its success. He was one of the first gatekeepers not to dismiss it out of hand. He passed it to Payne with a ringing endorsement. The rest is history. Sadly, he doesn’t get enough credit, and others have stepped in to claim credit where they have no business opening their mouths and hogging the spotlight. But, then, Hollywood has always had its mendacious Donald Trumps.

How does a writer get their first 1,000 sales in 2016, from your perspective?

I have no idea. Write something that people want to read. But, people are reading less and less, and because of self-publishing there are more and more books. It’s a tough world. I hate the publishing industry for how they’ve treated me, especially after Sideways, but in a way their winnowing process was good for the book business. Now, it’s a free-for-all. Which is good, in the sense that anyone can get their book published. Getting it read requires money and self-promotion. I don’t know the answer. It’s a tough question. The ultimate question, really.

How important are agents in 2016?

I’ve had a lot of agents in my career — film, publishing, and now stage. And managers. At their best, they can get your work to a network of connections that they covet – and they’re only as good as their connections. They’re kind of like gatekeepers to the gatekeepers, if you will.

At their worst, they’re manipulative, will openly lie to you, and often have so many clients that they don’t have time for you, but pretend they will. I truly like my current agents David Saunders and Susan Weaving in theater, but I particularly love my manager Brian Young at 360/Roc Nation.

Get a good manager. Remember, agents are salaried. If they make $100,000 a year, they have to do $1,000,000 in gross sales to break even for their umbrella company. It breeds a kind of ruthlessness. But, I understand its origins.

Getting an agent to sign you means almost nothing. So many neophyte writers equate that moment with their being a professional writer and that they’re going to be working. Wrong! I know a young writer who has had an agent and manager for three years and he hasn’t made a dime.

I don’t think agents are a negative, if you stay on the qui vive with them, but I’ve learned that you have to make your own action. If you wait for your agent to do everything you might be sorely disappointed in how your “career” is unfolding, or, rather, unraveling.

What advice would you give to someone who has just finished writing their first novel?

I’m sorry. I really don’t have any. Given today’s world where people have less and less time, and content (especially novels) is under siege by so many other forms of entertainment for peoples’ time (video gaming; streaming TV; ad infinitum, ad nauseum) I, personally, would not write a novel on spec, only if I was getting paid.

Okay, that’s my professional business opinion. On the creative side, I would say: find an original voice; don’t follow fashion; don’t go to stupid seminars; don’t read How To books; don’t follow the market; devour novels and become a devotee of the written word.
First and foremost: fall in love with words, with stories. Take risks. Be trailblazing. Don’t write with anybody looking wraithlike over your shoulder. Let it all hang out.

What advice would you give to someone who wants to write for film?

Watch movies, read screenplays – widely available now. Watch more movies. Become a movie or TV junkie. Write. More, not less. Write when you have something to write. Write when you know your characters, when you know your world, not just when you’ve had a cerebral hemorrhage of the imagination with some high-concept idea. Don’t write because you want to make money. Write a movie that you would want to see. Don’t go to any of those so-called writing gurus’ seminars. Worthless. Waste of your money. Don’t read books on how to write a screenplay. Worthless.

Develop your own sensibility by falling in love with movies or TV shows that you love. Write when you feel it wanting to pour out of you. If the writing’s not coming, abandon it and write something else. Always either be writing or be thinking about writing. Never anything else, if you can help it. It’s not an avocation. It’s a life. Sacrifice everything. I did, anyway.

Aspiring writers who tell me they’re going to give it a few years have, in my opinion, already sown the seed of failure. Are you kidding me? Sure, there are exceptions to the rule, but this is a life, not a hobby. Very few are going to make it, so you’d better give it more than anyone else, because you might be starting with less talent, or fewer connections — yes, nepotism and racism and gender and all kinds of other heinous factors play into it.

I do think you’ve got to put in your time in L.A. or N.Y., but probably L.A. Mine your connections. Make a short film. Just keep pushing against the system with your sensibility. Everyone will get their chance, but once you do, you’d better have the goods, because you might only get one chance, especially if you’re a woman, or a minority, or don’t have the resources that some of these people who make in the business have.

What’s the hardest thing about being a professional writer?

Living the life. People say to me all the time, “Rex, you must live a charmed life.” To which I always respond: “You wouldn’t want to live the life I’ve lived in order to live the ostensibly charmed life I’m currently living.” There shouldn’t be anything “hard” about being a writer. You should be doing it for the joy, for those moments of levitational transcendence – like when I was writing Sideways, it was such an almost out-of- the-body experience.

If you’re in it for the lifestyle, the lunches with agents at the Bel-Air Hotel and the 700-series BMW then I have nothing but contempt for you. The easiest thing about being a writer for me is the writing. The hardest thing is having to go to the mostly ignorant world with your work. And having to listen to what they say because they might be in a position of power and you have no choice but to listen to them.

But, every now and then they have something intelligent to say. Rarely, but they do. Learn when to listen; learn when to mostly ignore and stick to your guns. I wish all aspiring writers could realise one thing: producers, agents, managers, directors (who don’t write), actors… they’re all nothing without your words. Nothing. They need you. But, they will manipulate you, they will lie to you, they will try to get you to work for free. But, they need you. Without you, they are totally, truly, nothing, mariners without ships, charting in vain the lost continents of their dreams of finding gold.

Follow Pickett on Twitter @RexPickett or head to RexPickett.com for more.

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