Chekhov’s Gun and Red Herrings: Meaning, Rules, and Transgression in Storytelling


“If I think of somebody telling a story, I see a group of people huddled together, and around them a vast space, quite frightening.”  — John Berger

It’s probably important to start off by quickly distinguishing  between a “story” and “literature,” at least in a way that is, if not universally true, at least instrumentally valuable. Literary works often include one or more stories — did, almost always, until the twentieth century — which are used as starting points to launch all sorts of philosophical investigations into language, morals, structure, society, politics, and human behavior. Storytelling meanwhile (which will be the focus of this essay) refers to that tradition passed down from campfires and Aesop and early human history, where plot is the dominant element and engagement the primary end. Parable can occur too but is secondary, something that happens along the way or is woven in the with the narrative. The relationship between storytelling and literature then, at least as conceived here, is a spectrum between plot-driven and idea-driven texts, where the each tradition prioritizes one end more than the other. Some might simplify the narrative end of “engagement” to “entertainment,” but this strikes me as reductive — the Berger quote above illustrates a way in which engaging storytelling builds almost an abstract shelter for early man, an inner space in which structure engenders a desirable sensation of safety, predictability, and teleological meaning far removed from some “frightening,” meaningless, and ostensibly chaotic outer world.

Good storytelling is certainly an art, and all art forms develop principles or rules which, when followed, improve an artist’s odds of making a meaningful product. Art is consequentialist in this way — it isn’t an adherence to the rules itself which makes good art, it’s just that certain techniques, approaches, or decisions lend themselves to higher rates of artistic success. Chekhov’s Gun is one such narrative principle, a piece of advice popularized by the playwright Anton Chekhov, which counsels that all notable objects or details in a story should somehow contribute to its plot: “One must never place a loaded rifle on the stage if it isn’t going to go off. It’s wrong to make promises you don’t mean to keep.” This is arguably part of a larger principle of compressed or economic storytelling, where every event, character — basically every word and paragraph — goes to work in some meaningful, valuable, and irreplaceable way in developing a narrative or else keeping the reader engaged. In a broad sense, even elements like character development are merely means towards shuttling the reader from the first to last page of a story:

  • Worldbuilding creates a plausible system within which a conflict can take place.
  • Antagonists create or facilitate conflicts.
  • Allies make a difficult or seemingly insurmountable conflict plausibly surmountable.
  • Since they cannot be resolved status quo behavior or events, conflicts inevitably lead to change and variability in the narrative — which maintain our interest — as well as suspense, which piques our curiosity, the unknown drawing us onward.
  • Character development leads us to empathize with, and invest in, characters so we care in the first place whether they surmount said conflict, and will read on to find out.

Sometimes (often) good stories come with some sort of moral, psychological, or educational takeaway woven in as a secondary priority, so that they’re not only valuable (as entertainment) in the short-run, but have some lasting longterm benefits. This increases their utility to users (readers) and means they’ll be passed along and prized, often, with the great stories, along generations and, if this utility is universal enough, enduring cataclysmic cultural changes. Using this expanded definition of narrative ends, we can see how characters create applicable moral/psychological situations which can be easily extracted and extrapolated from by readers in a useful way: because they’re like us (and even non-human characters are almost always anthropomorphic) their conflicts are relevant, and the ethical dilemmas they face in dealing with these conflicts are similarly pertinent. When elements of a story don’t contribute to plot or parable, they’re not just neutral inclusions — they can actually devalue a story by making it less engaging or demanding extra time and effort from the reader in order to extract the actually valuable bits. Economy is a pretty important and established principle of narrative, especially in mediums like film where every minute of screentime is not just an imposition on the viewer but can cost the production company tens or even hundreds of thousands of dollars. Sontag even speaks at a bit of length with John Berger on economic storytelling, though her quote, coming as it is from such an established and well-read literary mind, is a more a testament to narrative economy’s importance than it is an explanation of why this might be so:

“The most powerful form of storytelling is very compact, and if its very compact, it’s likely to be very economical in its details, and therefore this economy can be experienced by us with our modern ways of looking at things as something abstract and in that sense it may take on a certain universality.”


One of the things we know about rules, however, is that they’re not always followed. And in fact, it’s at the very instant when a rule is broken that meaning is created. The reason for this is three-fold.

For one, rule-abiding is, to the experienced artist, the default mode of production. If an artist or author is breaking a rule, there is always a reason for it. In deviations and transgressions, we find areas of deliberate, reasoned aesthetic or artistic choices, in which, if the artist or author is worth his salt, something very interesting is likely to be happening. Most works of art are running primarily on default decisions, on following tradition or the rules or the norm — there are simply too many infinite possibilities and decisions to be made for this not to be true. Most books are written on paper, with black ink, professionally published, and if an author has specified otherwise there is bound to be a rationale behind it. If we know this rationale is purely artistic — that is, it was chosen only for artistic reasons, rather than done out of limited technical ability or financial funds or commercial incentives by the author — then this transgression of norm is bound to be artistically interesting. We can say the same about paintings done on materials other than canvasses, or with materials other than standard paints; we can say this about the first deviations from realism and mimesis, both literary and visual; about any active straying from the temporal, ideological, or artistic status quo.

Two, consuming a work requires some degree of orientation on the part of the consumer. Largely because users know the above properties of a work — know, that is, that they should pay attention primarily to the odd or original qualities to extract value — they’re left dizzy and disoriented when too many elements are subverted or upended from status quo by the creator, and when there’s nothing familiar to cling to in getting a bearing on surroundings. Where to pay attention? Why is the creator doing what he’s doing and what does it mean? What am I even looking at right now, and what should I be looking at? No, all works are on strict rations for how much artistic deviation and transgression they can pull off effectively. This means all the more than when a creative is choosing to deviate from the rules or norms, they’re going to maximize its impact; use it on something important.

Three, users/readers/viewers aren’t consuming a work in a vacuum. They’ve likely consumed many similar works before, of a similar school, culture, or era, of the same medium or by the same artist. This means they have all sort of expectations for what’s going on, and in a narrative, what’s going to happen. Even if they can’t explicitly vocalize them, good readers are, from repeated past exposure, aware of narrative rules like Chekhov’s Gun, which help them stay oriented and make predictions. Transgressing rules, then, can be incredibly powerful and effective — in fact, transgression can only be significant in the first place because a rule or expectation exists. The red herring, itself a valuable narrative tool, only exists because readers expect narrative economy, expect Chekhov’s Gun, expect that every element pulls weight in a plot. In almost dialectic fashion, surprise, the subverting of expectation, requires expectation to exist; misdirection requires the directing of a user. This is why a series of books like Knausgaard’s My Struggle couldn’t very much have red herrings: it’s understood by readers that compressed storytelling à la Chekhov’s Gun isn’t a law of his fictional landscape. The books are intricately detailed and based on Knausgaard’s real life, on the external, “vast space” of the external world, a world which we know doesn’t abide by the same predictable, meaningful structure of a good narrative teleology. It’s true that Knausgaard curates the details he includes in the books, but not nearly to the degree of a good, economic story (this is because My Struggle is literature, not just a pure plot-and-parable narrative, which means it has all sorts of ends beyond engagement and instruction: it’s trying to do things like explore the mundane and ordinary; it’s undertaking an almost documentarian, voyeuristic project about the author’s life; it’s asking philosophical questions about death and intimacy in ways that go beyond the typical bounds of pure narrative). By the time Knausgaard (the autobiographical protagonist Knausgaard, that is) goes to the birthday party of his young daughter’s friend, early in the second novel, we know the rules of My Struggle’s project; we bear no expectation that his extensive descriptions of children at play will contribute in some meaningful way later in the book or series. We’re not surprised by its lack of contribution to the plot, and so we aren’t trying to figure out how it’ll tie in later on, or in which way a newly discovered personal habit of his daughter will end up being her fatal flaw, her final undoing. Misdirection isn’t possible because we aren’t expecting to be directed. It makes sense then that in novels which veer closer on the spectrum to storytelling than literature; novels which carry with them reader expectations of narrative compression (Agatha Christie novels, perhaps, where the primary intended effects of a work are thrill, anticipation, surprise, and suspense) red herrings will be more powerful (and desired) devices

Beyond red herrings, which are ways of making a plot more interesting by making it less predictable, deviating from the principle of Chekhov’s Gun doesn’t happen in pure storytelling for obvious reasons — why would something nonessential to the plot be included in a work where plot is the primary or only end? But when readers go into a work of literature expecting mostly a story, expecting that plot is a dominant end, and this expectation is subverted, the reader starts trying to track down why. What is this long digression, or this seemingly unrelated (from a plot perspective) parallel storyline doing? If not to drive plot, why has it been included? And it’s then that this end user is driven to discover why, and in turn extract whatever non-narrative, literary utility the passage might contain.


William Cobbett’s Political Register 1802 (source of term red herring): “When I was a boy, we used, in order to draw off the harriers from the trail of a hare that we had set down as our own private property, to get her haunt early in the morning, and drag a red-herring, tied to a string, four or five miles over hedges and ditches, across fields and through coppices, till we got to a point, whence we were pretty sure the hunters would not return to the spot where they had thrown off.”


Susan Sontag, John Berger, To Tell A Story (1983)

Venkatesh Rao: The Chinese Compressibility Parable

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2 responses to “Chekhov’s Gun and Red Herrings: Meaning, Rules, and Transgression in Storytelling”

  1. […] innovation and stifling creativity. But I’d argue exactly the opposite is true — that interesting, meaningful transgression and deviation requires rules and categories, and that without genre frameworks within which to work, artistic innovation would be, if not […]


  2. […] yields impenetrable noise, and the most interesting moments of an argument or idea come in the minor variations, the small differences, the details in presentation, execution, and […]


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