Donald E. Westlake is perhaps the definitive writer’s writer, having published more than one hundred books under various names, including Curt Clark, Tucker Coe, Samuel Holt, Edwin West, Judson Jack Carmichael and – most famously – Richard Stark. Why so many names? Partly because Westlake showed admirable brand management by choosing different names when writing in different genres, and partly because he was so incredibly prolific that he needed multiple names so publications could run his stories side by side without sacrificing a sense of variety.
Westlake was a three-time winner of the Edgar Award and a Grand Master of the Mystery Writers of America, as well as an Academy Award nominee for his script writing. His work has been adapted into numerous movies (a few more than he adapted himself) and he is most famous for his comic mysteries starring melancholic criminal John Dortmunder and (as Richard Stark) his crime thrillers starring steely, workmanlike criminal Parker.
So, what can Donald E. Westlake teach you about writing? The answer is a lot, but let’s begin with a lesson that he seems to have taught again and again and again.
1. The rules (of writing) are made to be broken
Poring over Westlake’s wise words, the first thing to jump out is just how many tenets of good writing he left by the wayside.
Now, in art, we all know there are no rules. Even when we talk about what authors ‘should’ do, it’s only in the sense that there are things that tend to work for most writers and readers. Even so, Westlake repeatedly did things that any sensible editor would advise authors against.
For example, should you plot a book out ahead of time or let it unfold in the writing? It depends on what kind of writer you are, but one technique that few people would advise is to think up a title and just start writing. Even then, perhaps you’ve got a doozy of a phrase that makes starting with the title the right call for a given project, but in his Parker books, Westlake treated striking out from a title as the rule, not the exception.
I don’t outline or plan ahead but every day tell myself some more of the story. I know the characters and I know the subject, and usually I can figure out what happens next. Sometimes the title is almost the only seed needed. Breakout came about when I realized that, in all these years, Parker had never been jailed except once before the first book. Get him arrested, and watch how he handled it. At the end of part one he’s out of jail, but not out of trouble, and at that point I came down with bad Lyme disease, in the hospital four days, unable to work for six weeks, and I kept saying, “Well, at least he’s out of jail.” We both hated the experience, and we both worked very hard to get him out of there. When I got back to the book, I realized the title meant the whole book so the entire thing is Parker clawing himself out of places he doesn’t want to be. They usually find their subject and their path that way, and if they don’t I simply give up writing, move to another city and use a different name.– Donald E. Westlake, ‘An interview with Donald Westlake Author of the Parker novels’
A couple of Westlake’s books never even justify their titles, or do so with a short passage that’s clearly been added just so the title makes sense. It’s a ludicrous state of affairs, and yet… the books are great, so who cares?
But that’s planning, and perhaps just a fancy way of telling the story as you go, so how else did Westlake break the rules? Well, since we’re talking about Parker, can you imagine any editor suggesting that a writer base their novel around a mean, unlikable character who doesn’t even let the reader inside their head?
When Bucklyn Moon of Pocket Books said he wanted to publish The Hunter, if I’d help Parker escape the law at the end so I could write more books about him, I was at first very surprised. He was the bad guy in the book.
More than that, I’d done nothing to make him easy for the reader; no smalltalk, no quirks, no pets. I told myself the only way I could do it is if I held onto what Buck seemed to like, the very fact that he was a compendium of what your lead character should not be. I must never soften him, never make him user-friendly, and I’ve tried to hold to that.– Donald E. Westlake, ‘An interview with Donald Westlake Author of the Parker novels’
Of course, anyone can get lucky, and a character like Parker might be fun for a one-book romp… or a twenty-four book series in which he doesn’t significantly change, develop, or open up to the reader.
The big question was, could I go back to him, knowing he was going to be a series character, meeting the readers again and again, and not soften him. No sidekick or girlfriend to have conversations with, no quirks or hobbies. That was the goal.– Donald E. Westlake, ‘Donald E. Westlake Interview’ on Ed Gorman’s Blog
Somehow, this worked too, and this might be the point at which you’re beginning to think that Westlake had help. That, true to his coterie of pseudonyms, he had a crack team of editors and beta readers behind him, helping him draft and re-draft until things were just right.
I didn’t show The Hunter to anybody for input. I’ve rarely done that with any book. In fact, the only time I can remember doing that was with my first mystery, The Mercenaries, when I wasn’t at all sure what I was doing and I showed the first draft to a writer friend of mine, Larry Harris (who later, for some reason, became Larry Janifer), because I knew he was a good writer and a good editor and far better attuned to the market than I was. He called and said he wanted to come over and talk. When he got to the apartment he had the manuscript box in one hand and a six pack of beer in the other, and he said, “We’re in trouble.” We went through the manuscript, and if there was a beginner’s mistake I hadn’t made I can’t think what it might be. It was a terrific learning experience, and the next draft sold to Lee Wright at Random House, who later became Larry’s editor as well. Otherwise, my first three readers, only when the book is done, are, in order, my wife, my agent and my editor.– Donald E. Westlake, ‘Donald E. Westlake Interview’ on Ed Gorman’s Blog
So, Donald Westlake was the kind of writer who didn’t solicit feedback, barely planned ahead when writing his stories, and based a series of books on a character who offered no particular reward to returning readers. How did he do it? Perhaps by scaffolding his riskier decisions with an acute appreciation of genre conventions? Not really – Westlake’s many names were a tool to help him write anything he wanted without confusing his audience, but beyond that, he didn’t care much for categorization.
I don’t think the distinction between genre and literary fiction is useful. We’re all working with the same two things, story and language, and if you fail with either of those it doesn’t matter what label you put on it.– Donald E. Westlake, ‘An interview with Donald Westlake (aka Richard Stark)’ on Compulsive Reader
I could go on, but I think we’ve established that as a writer, Donald E. Westlake had a habit of going against what’s usually considered pretty good writing advice. Does that mean such advice is nonsense? No – it’s what most people need to hear at the point in their career at which they’re looking for advice. Westlake defies these rules not because they’re wrong but because they’re not really rules, they’re guidelines, and if you spend your life writing as prolifically as Westlake managed, you’ll figure out better guidelines – guidelines that emerge from your own style – in no time at all. Especially if you…
2. Keep experimenting
It’s tempting to look at Donald E. Westlake’s pen names and just think of him as someone so prolific he needed multiple identities to keep up with his work. That’s not inaccurate, but it misses the point that Westlake adopted a new pen name when he tried something his readers wouldn’t expect from Donald E. Westlake. The fact that he has so many of them is an indication of how often this happened.
Not only that, but Westlake’s constant experimentation was a conscious decision. Shortly, Westlake will explain how his writing style differs from that of his alter ego Richard Stark, and that’s the kind of thing you only discover through experimentation.
The third book I did under my own name, before I did any comic novels, I wanted to try an experiment. There are a couple of writers I admired who were very good at giving the character’s emotion without stating what that emotion was. Not saying “He was feeling tense,” instead saying, “His hand squeezed harder on the chair arm,” as if staying outside the guy. I wanted to try doing that. I wanted to have a really emotional story in which the characters’ emotions are never straight-out told to you, but you get it. The first Parker novel was written right around the same time, sort of doing that again. It was a deliberate attempt to leave the emotional statement alone.– Donald E. Westlake in Christopher Bahn’s ‘Interview: Donald Westlake’
What’s truly fascinating about Richard Stark is that Westlake lost contact with him for twenty-three years, unable to write in Stark’s voice until, after more than two decades, the hard-boiled crime writer returned. Through experimentation, Westlake discovered an alternate voice so powerful that it operated like a separate entity, and here’s the kicker – Richard Stark stopped writing for twenty-three years, but Donald Westlake kept working through all of them. So, if you’re suffering from writer’s block, consider setting yourself free with some literary experimentation. It turns out you may have a whole other career locked away in your mind.
3. It starts with the words
It would be silly to truly suggest that Richard Stark was a different ‘personality’ – an idea that Westlake himself mocked – but in terms of craft, it’s accurate to say that Stark is a different writer. In fact, Westlake’s approach differed from Stark’s so much that the Westlake book Jimmy the Kid is a successful parody of Stark’s work – Westlake had enough distance from Stark to take the latter writer to task for his writing style and convenient plotting.
In fact, it’s possible to be a Westlake fan without enjoying Stark’s work, and vice versa. This comes down to more than genre or subject matter; Stark really does read differently. Westlake was aware of this, and he put the difference between he and Stark down to the first and most fundamental set of choices a writer makes about their craft.
In the most basic way, writers are defined not by the stories they tell, or their politics, or their gender, or their race, but by the words they use. Writing begins with language, and it is in that initial choosing, as one sifts through the wayward lushness of our wonderful mongrel English, that choice of vocabulary and grammar and tone, the selection on the palette, that determines who’s sitting at that desk. Language creates the writer’s attitude toward the particular story he’s decided to tell. But more than that, language is a part of the creation of the characters in the story, in the setting and in the sense of movement. Stark and Westlake use language very differently. To some extent they’re mirror images. Westlake is allusive, indirect, referential, a bit rococo. Stark strips his sentences down to the necessary information.– Donald E. Westlake, ‘WRITERS ON WRITING; A Pseudonym Returns From an Alter-Ego Trip, With New Tales to Tell’ in The New York Times
4. Don’t overdo the description
Okay, we’ve explored the rule-breaking, experimental side of Donald E. Westlake, so now let’s turn to a few solid, dependable instructions.
First, some advice we gave in 7 Ways You’re Treating Your Novel Like A Screenplay (And How To Stop) – don’t get too detailed about describing your characters’ exact physical actions.
Novelists, when their characters drive cars, never feel compelled to describe precisely what the physical actions are of hands, feet, eyes, knees, elbows. Yet many of these same novelists, when their characters copulate, get into such detailed physical description you’d think they were writing an exercise book. We all know the interrelation between the right ankle and the accelerator when driving a car, and we needn’t be told.– Donald E. Westlake, Dancing Aztecs
Perhaps it’s no surprise that with his screenwriting experience, Westlake would be perfectly placed to recognize the difference between what works in a visual medium and what works on the page.
5. Do. Your. Research.
Westlake’s research is something else, to the extent that he reminisces about receiving letters from prisoners wanting to ‘talk shop’ about the crimes in his novels. His heists are perfectly detailed, and whether the score is coins, stamps, or diamonds, he always seems to have an inside knowledge of how everything works (and how it can all go wrong).
Perhaps no book proves this more than the The Outfit. In this novel, the protagonist goes up against Westlake’s stand-in for the Mafia. Part of his efforts include contacting thieves around the country, asking them to pull the ‘forbidden’ heists they’ve always dreamed of but which the Outfit wouldn’t allow. What follows is a chain of engaging, perfectly described heists, each of which could have supported its own novel.
Westlake gives the impression of understanding every character, every job, and even every building down to the ground, and that’s the kind of insight that only comes from truly researching your subject matter.
6. Write every ‘day’
We began with a litany of common writing advice that Donald E. Westlake just didn’t follow, but at least he stood by the most given (and least followed) piece of writing advice there is: write every day.
I get up at a normal hour, and it’s two or three hours at the desk in the morning, beginning with looking at what I did yesterday and making any changes in it, then using that springboard to go forward. And then usually an hour or two in the afternoon. The thing that I prefer, when I’m working on a book, is to do a seven-day week, because it’s easy to lose some of the details of what you’re doing along the way. Years ago, I heard an interview with violinist Yehudi Menuhin. The interviewer said, “Do you still practice?” And he said, “I practice every day.” He said, “If I skip a day, I can hear it. If I skip two days, the conductor can hear it. And if I skip three days, the audience can hear it.” Oh, yes, you have to keep that muscle firm.– Donald E. Westlake in Christopher Bahn’s ‘Interview: Donald Westlake’
Life is hard, and we all have to make a living, so I’m not going to pretend that it’s sensible to suggest that amateur authors write every day. That said, there’s a place for Westlake’s Menuhin story in your personal philosophy of writing. Skip one day and only you can hear it, skip three days and the audience can tell. What a ‘day’ means to you will vary, but there’s a truth to this idea that might just help you return to the keyboard/typewriter/pen/quill more often than you would otherwise.
7. If it works, it works. If it doesn’t, ditch it.
We can’t end with Westlake championing a firm rule, so let’s conclude with the attitude underlying that ‘rules are meant to be broken’ approach – if something about your writing works, let it work, but as soon as it doesn’t, get rid of it. This is the key to understanding Westlake’s apparently anarchic approach to conventional writing wisdom; he knew a good idea when he wrote it, but he wasn’t sentimental about what ‘should’ be done. In his foreword to Stark’s Backflash, Lawrence Block explores this idea on a practical level.
In each book’s initial sentence, something happens and Parker reacts. When this happened, Parker did this – and we’re off and running.
When the guy with the asthma finally came in from the fire escape, Parker rabbit-punched him and took his gun away.
When the woman screamed, Parker awoke and rolled off the bed.
When the knock came at the door, Parker was just turning to the obituaries page.
When the bellboy left, Parker went over to the house phone and made his call.
… There are a few books that open differently – The Black Ice Score, The Sour Lemon Score, Deadly Edge. I don’t think Don wanted to be a slave to anything, even if it were something of his own devising. A title sequence would be maintained until it became unwieldy, or tiresome; an opening would serve until a variation seemed to serve better.– From Lawrence Block’s foreword to Richard Stark’s Backflash
This is how Westlake managed to be both a uniquely independent and successfully formulaic writer; the formula is only worth following while it works. Try to add a little of this recklessness to your writing, especially if you want to be prolific. And if you’re asking how you’re supposed to guess what’s going to work and what isn’t, I refer you back to the second entry on this list.
Lemons Never Lie
Donald E. Westlake demonstrated a fluid relationship with words that’s still the envy of most authors, and like most masters of the craft, his example can teach us even more than his advice. Be bold, be reckless, be prolific, and embrace whatever improves your writing, be it a winning formula or an unexpected deviation from the norm. Do all that and it might even turn out there are whole other writers living in your head.
Which of the above advice works for you, and which would you never follow in a million years? Let me know in the comments and, if you feel like you recognize that opening line about the asthma, check out Improve Your Exposition Immediately With This One Simple Tip for a deeper dive into what makes it work so well. You can also try How To Write A Character Who Can Carry A Series and Enthrall Your Readers With A Complex And Tantalizing Antihero for the exact kind of great advice that Westlake didn’t need to follow.