Rediscovering Irony

Counterprogramming cancerous sincerity and the cult of authenticity with AI assistance

As above, so below. It seems to me that the problem of pushing AI past its most important limitations, and the problem of rescuing human culture from its most important pathologies at all scales, from claustrophobic and increasingly diseased cozyweb enclaves, to calamitously stupid geopolitical theaters of violent performativity, are the same.

The problem is insufficient irony, to check and balance a culture (emphasis on cult) of sincerity and authenticity turned cancerous, over nearly two decades of unchecked and critically unexamined metastasis.

Since at least 2008, sincerity has been uncritically valorized, and irony systematically mischaracterized, demonized and devalued, obscuring the dark and deleterious aspect of the former, and the generative potentialities of the latter.

In this essay, I want to try and restore balance to the universe by reclaiming irony in its fullest, most potent sense — the capacity for holding two inextricably, subatomically entangled ideas in juxtaposition, in word and deed, in order to deal with realities that are ambiguous down to their deepest core.

While not the main purpose of this essay, I also want to go on a bit of a polemical side quest to dethrone sincerity and authenticity from the undeserved status they have ascended to in our time, which has resulted in great harm that continuous to compound.

And here, I mean sincerity and authenticity broadly: sensibilities that orient around stable, unitary meanings in words and deeds, holding them to be superior moral goods purely by virtue of their not being ambiguous. The self-certain sincere can be found all over the political and cultural map. Self-importantly sincere conservatives and progressives might not agree on a lot, but one thing they do agree on is that anyone capable of expressing two thoughts in the same utterance is necessarily a conniving and hypocritical “elite intellectual.” Self-involvedly sincere artists and smarmy and self-congratulatory entrepreneurial types might hate and snark at each other, but both agree that all irony is necessarily degenerative cynicism that all creative doers ought to resist. Self-certain religious moralists and radical environmentalists might be at odds on every moral question, but both agree that the devilish business of entertaining two ideas in tension within a single thought can only be the result of debased, depraved immorality.

Give a dog a bad name and hang him. Irony, charged with, and reduced to, simple hypocrisy, cynicism, and outright immorality, has been the consensus villain of our era.

As we shall see, all the charges against irony can in fact be laid at the door of the ecology of competing sincerities, and that irony, far from being an enervating drain on the collective psyche, is in fact its sole reliable source of generativity and liveness. It is in fact sincerity that is the deadening drain.

A society that does not cultivate a systematic capacity for, and literacy in, ironic modes of engaging reality, is doomed in precisely the way we seem to be doomed right now.

Until quite recently, making this argument has been not just difficult, but pointless. Sincerity is a fear response to the ambiguity of reality, and the practice of irony takes a particular kind of courage that the sincere not only lack, but in a masterful display of self-delusion, label cowardice, even as they identify their own shrinking retreat from ambiguity the best sort of courage.

The sincere not only don’t see it that way, they don’t see it at all. A benefit of deliberately suspending or destroying the natural human capacity for irony is that you cannot at once entertain the twin thoughts that you might be noble, and an asshole, at the same time. And of course, the sincere choose to believe in their nobility, and energetically repress the possibility and evidence of their own assholery from their self-mutilated one-track minds.

We must begin the story with Rousseau. The original Noble Asshole.

Noble Assholery from Rousseau to Graeber

Something like this essay has been brewing in my head for over a decade, but I just didn’t have all the pieces in my hands to make the complete argument.

The final piece of the puzzle came from The Infidel and the Professor, which I’m reading this month for our book club. It is an account of the long friendship and mutual influence of David Hume and Adam Smith. What caught my eye, however, was the book’s account of a marginal episode — Hume’s spat with Rousseau.

In the account of the spat, Rousseau comes off as a serious nutjob. A paranoiac with a persecution complex, who got along with nobody, and made everyone else pay for his fragile temperament. The spat was remarkably silly, and had nothing to do with the philosophies of either. It was not a philosophical spat, even though there is clearly raw material for philosophical conflict in their juxtaposed works.

Here’s what happened: Hume went out of his way to arrange a kind of political asylum for Rousseau in England after he’d pissed off most of the Continent, a kindness that Rousseau accepted with great reluctance and poor grace only when he had no choice. The kindness soon turned into fuel for his paranoia, and he developed an elaborate conspiracy theory based on the idea that Hume was out to get him for some reason.

This surprised me. In my headcanon Rousseau, as the anti-Hobbes,¹ author of a state-of-nature origin myth for humanity that is rooted in cooperation rather than conflict, and a theory of social contracts that would suggest a harmony-seeking temperament, had been cast as a pleasant, collegial fellow, quite unlike the bloodthirsty Hobbes.

Apparently he was not. By all accounts, he was an uncollegial asshole.

Seems like among other things, Rousseau also pioneered what I thought was the modern adverse selection phenomenon of compensatory creativity, where people produce works that mark them as authorities on subjects defined by their weaknesses rather than strengths. Karl Popper’s great work was ironically dubbed “The Open Society by One of It’s Enemies” by a student, and in a similar vein, we might dub Rousseau’s collective works “How to Live in Harmony with Nature” by Mr. Alienated Disharmony. Someone observed recently that Eat, Pray, Love fits this pattern too, in light of the author’s later weird arc. There’s probably a whole essay to be written about compensatory creativity. I probably fit the pattern too. I wrote Tempo about timing and decision-making because I am really bad at real-time decision-making and generally live in a state of atemporal indecisiveness.

I want to add a rather personal data point here, to make this an n=2 case at least. I don’t like to speak ill of the recently dead, but in this case it serves a purpose.

The account in the book (from a Hume-sympathetic, but also objective) point of view reminded me very strongly of a contemporary thinker, the late David Graeber. Some of you know about my one skirmish with Graeber in 2011, where he took deep umbrage at a passing mildly critical remark I made about Debt in a blog post, teasing my upcoming book review. Graeber somehow found the post (I presume he had a Google Alert set) and posted a series of combative comments on the blog post, which made me decide not to post the full review I had been planning (which would have been a mix of positive and critical, and overall mildly net critical). He later blocked me on Twitter. Not that I’m comparing myself to Hume, but I’m glad I chose to disengage where Hume, rather unwisely, imposed a favor on Rousseau despite warning signs that it would end badly.

I think enough time has passed since Graeber died (2020) that I can share my opinion of him without being an asshole myself: The guy, like Rousseau, was an asshole. And this is not just my own minority opinion.

Shortly after my own run-in with him, I learned that I wasn’t the only one to face the unexpectedly wide-roving wrath of The Graeberian Inquistion. Picking fights with a thin-skinned over-sensitivity to any criticism of his ideas (like Taleb, but with less substance underwriting the curmudgeonliness) was a pattern with him. I also learned, from a former student of his, that Graeber’s personality was marked by a kind of extreme extroversion, which made him unable to think except in the context of a social nexus and live dialogue (the student characterized him as the opposite of an aspie, what I had earlier in the year dubbed a codie). The guy apparently couldn’t think in isolation. He needed to do his thinking in an active web of people he was discoursing with. And presumably, going by the experiences of myself and several others, the web had to be in a constant state of active, acrimonious conflict to reassure him that he was alive and thinking. This is the opposite of my temperament. I do most of my thinking on my own, and to the extent I do it in an active social web, I prefer that web to be mostly in a state of harmony.

I don’t know how accurate the student’s characterization of Graeber is, but it strikes me as remarkable that the central feature of Debt is a theory of economic interactions that rests precisely on the notion of a nexus of live relationships as the primary unit of analysis, rather than the decisions and actions of individual economic agents. And like Rousseau, he too offered a (grandiose and revisionist) origin myth for our species, and was politically active on similar fronts (Rousseau wrote on inequality, Graeber was a central figure in #Occupy). It is a bit uncanny that two thinkers, separated by 300-odd years, had the same abrasive, asshole personality, and same interest in themes of harmony, cooperation, and so forth.

And the pattern goes beyond this n=2 dataset. As Jo Freeman argued in a classic 1972 essay, The Tyranny of Structurelessness, which the internet keeps rediscovering every couple of years, it is no accident that the prospect of a cooperative, egalitarian utopian harmony reliably attracts those with the worst possible temperament for pursuing such visions, with experiments always predictably dissolving into toxicity.

But I want to make a stronger argument than that of simple assholery. Rousseau (and arguably every reactionary primitivist since, across the political spectrum), wasn’t just an asshole. He was a noble asshole. How do I know this? Because I learned from my book that aside from picking paranoid-delusional fights with people trying to help him, he apparently also tried to start a kind of religion of sincerity.

While I was aware of Rousseau’s general historical significance as a founding father of all modern schools of atavistic/primitivist reactionary yearning and humanist religiosity, I was not aware of this explicit engagement with sincerity in what seems like a startlingly modern-seeming sense. If you look carefully, you’ll find the same obsessive fetish for sincerity (or its near-synonym, authenticity) in every tradition that can be traced back to him in some way.

And the primary payoff of this striving towards sincerity seems to be arrival at a sense of oneself as somehow nobler than others, regardless of the evidence of the consequences of one’s actions int he world, one way or the other. Simply doing whatever it is you decide to do with sincerity and authenticity, apparently, is sufficient to establish your nobility. Even if you burn down the world along the way. You can always assert after, with fetching humility, that you did your best, and couldn’t have known. Of course you couldn’t. To have known would have been to doubt. To doubt would have meant entertaining more than one thought at a time, which would have meant flirting with irony. Dubito ergo cogito ergo sum and all that.

This is of course, not just a fallacious pattern of reasoning, but a smarmy, self-serving, asshole pattern of reasoning. Hence, noble asshole.

Naturally, there is a lot of commentary about the connection, which you can explore if you like. My one takeaway from a drive-by scan is that what I thought was an evolution of a reactionary impulse (again, I emphasize, both left and right) dating back to Rousseau is in fact no more than a rhyme. There has been no significant evolution as far as I can tell. The ideas pave the same intellectual dead-end they did in the 17th century, which of course is a feature for people who only want to go backwards.

Today’s humanist yearners for sincerity, authenticity, and re-enchantment, both on the left and the right, don’t seem to have learned a lot since Rousseau. They’re rehearsing patterns he pioneered, just with various extra steps like turning off cellphones and congratulating each other for being based.

And technological modernity qua technological modernity really has nothing much to do with it beyond serving as a source of periodically updated Macguffins to feature in endlessly rebooted morality tales starring noble assholes. The alienation that drove Rousseau paranoid in the 17th century is of the same sort that drives modern reactionaries paranoid.

Now, if you’ve been a long-time reader, it probably doesn’t surprise you to learn that I have no patience for either the early modern or contemporary versions of this sincerity religion.

I didn’t like David Graeber, and I doubt I’d have liked Rousseau. But reading this book, and linking their shared idea space (encompassing things ranging from essentialized relations to nature, to inequality, to the nature of “natural” human relations) to sincerity, has given me some insight into why I reflexively reject both the fundamental philosophy itself, and social engagement (even superficial) with people who subscribe to it. Not to put too fine a point on it, they’re mostly wrong about everything, and a joyless grind to talk to at best. At worst, dealing with them is dealing with relentless, exhausting, assholery.

I’ve learned a few things since my 2011 skirmish with Graeber, and I now have a very finely tuned “sincerity radar” that allows me to safely cross the street when I see an aggressively sincere person coming towards me.

The Problem With Sincerity

This might seem like an odd stance to adopt. I mean, what’s not to like about sincerity? Does being suspicious of sincerity (either aspirational or real) as a fundamental dispositional trait imply that I endorse and practice insincerity?

Sometimes, yes. When I am indifferent to the stakes of a situation, and don’t care for the people involved, I can practice little white insincerities without a qualm, and lose no sleep over it. I can even be manipulatively insincere, (a term of art from a fine 2x2 that anchors Kim Scott’s book Radical Candor). But mostly, I’ve become wise enough to almost never put myself in a situation where I’m forced into insincerity.

Insincerity might be the on-the-nose antonym of sincerity in the English language, but it’s a rather shallow sort of opposition. My aversion to sincerity runs deeper, and is rooted in a different opposed disposition — irony. So let’s set insincerity aside and talk of sincerity as the antonym of irony.

For the last couple of decades (dating at least to the hipster era through the GFC), sincerity (and its near-synonym in our current zeitgeist, authenticity) have been framed in opposition to irony, rather than insincerity per se.

Irony understood in a particular bad-faith way, as a sort of ennervated cynicism and hypocrisy that excuses itself from imperatives to action through sophistry, and also smells of insincerity.

This is not entirely unfair. Irony as a cultural phenomenon rooted in the 80s (and I’m fundamentally an 80s kid) does in fact often reduce, in practice, to a kind of aestheticized learned helplessness under a veneer of sophistication. And it does often indicate insincerity when taken together with another sign — visible success that is the result of selfish striving. There was a great piece about this kind of “irony” in The Onion in 2005, Why Can’t Anyone Tell I’m Wearing This Business Suit Ironically, where irony mutates into a rather banal sort of hypocrisy indistinguishable from “selling out” a sincere subculture.

If your inaction bias is selective in this sense — sophisticated helplessness in the face of imperatives that might do collective good, but high-agency energetic action where personal rewards might accrue — you’re not being ironic or even cynical. You’re simply being an insincere hypocrite.

But this, I’ll argue, is a degenerate, shallow kind of irony; a cosmetic variety that fails to capture the energizing potentialities that lurk in what I’ll call dense irony (I’ll explain the adjective in a minute). Shallow irony is often comorbid with insincerity, double standards, and hypocrisy, but dense irony comes from a different place, and has different effects on both minds and the world.

I tend to forgive people who haven’t thought too much about irony if they harbor this reductive understanding of irony. The bad faith attends the views of those who ought to know better.

It is also worth distinguishing ordinary sincerity (such as anyone might practice in giving a straight answer to a straight question when there is no reason to be devious or indulge in doublethink/doubletalk) from what we might call devout sincerity, the antithesis of dense irony.

Devout sincerity is the religion we’re talking about here, which has been part of the cultural landscape since Rousseau at least, and is currently the dominant cultural and subcultural mood. Devout sincerity is the attitude that leads you down the road towards eventual noble assholery (a great example is in the movie Big Kahuna, where the ironic protagonists, two marketers played by Kevin Spacey and Danny DeVito, are betrayed by a younger employee whose actions in the story can only be described as noble assholery). That it is often rooted in personal pain does not, in my opinion, excuse it.

Dense irony is, I suspect, my native disposition (not least because I grew up in the 80s), and the reason I reflexively avoid sincerity. To get at what dense irony is, it’s easiest to approach the philosophical posture via its linguistic heat signature — ambiguous utterances.

Irony in Speech

In sophisticated language, irony is when the intended meaning is contrary to the surface meaning. Or to generalize slightly but powerfully, as the robot devil sang it in Futurama, “The use of words expressing something other than their literal intention!”

The rhetorical intent and affect accompanying a particular ironic utterance can vary (sarcasm, sardonic fatalism, cynicism, humor, absurdism, logical contradiction, Zen mu-ishness, and rarer kinds like quixotic energy) but the characteristic feature is a single utterance with two meanings in tension, with or without indication of which one is actually meant. The most interesting kinds of irony — and the ones to which I will attach the adjective dense — are the latter kind, where the utterance destabilizes meaning by pluralizing it, without indicating a “right” answer. Often, this sort of irony cannot easily be assigned an affect label. It’s just — unsettling.

Why is dense irony so attractive to certain sensibilities, whether or not they benefitted from the cultural-developmental conditioning of the 80s? Why would you want to consume or produce semantically unstable utterances? Why would you want to get good at it, through cultivation of unholy consumption tastes and production crafts?

And make no mistake irony, unlike sincerity, does take cultivation. It is a skilled mode of language use; one that takes more energy, not less, despite the association between irony and lassitude. I generally have to be in a high-energy. high-lucidity mood to produce ironic writing or speech. Injecting more than one meaning, especially in tension with each other, into words, is work. Irony is a kind of proof of work.

Why would you put in this kind of work? Why not keep language simple?

The devoutly sincere often assume the sole intent is to weaponize language to subvert and corrode sincerity. That the ironic are particularly out to sadistically inflict psychological torture on noble innocents too dumb to see past confirmatory literal/surface meanings in polysemous utterances. That the ironic are merchants of doubt, out to destabilize the psyches of those who possess the courage of their convictions, motivated by resentment, envy, or other base motives.

This broad understanding of irony is, of course, at the root of the bipartisan anti-intellectual tendency in modern American politics. To first order, to be an untrustworthy elite intellectual in America is to traffic in irony. Something the evil French do, not honest Americans.

Curiously, in the last decade, a loftier strain of intellectual anti-intellectualism has emerged in America, that believes it can “do” intellectualism without irony.

But whether they identify with the simple folk (who view themselves as clever and intelligent but not-intellectual) or contrarian intellectual traditions that eschew irony, the sincere, in my experience, tend to be rather self-involved humanists who assume everything is, if not about them personally, at least about an anthropocentric conception of human that they aspire to. And that irony, specifically, is no more than a weapon of dehumanization wielded against them.

This is… cute. To imagine that an entire psychographic, arguably a double-digit percentage of the population, adopts a particular cognitive posture purely to undermine another psychographic that is rather too full of itself, to the point that it imagines the entire cognitive universe of our species revolves around them.

See, the thing is, irony is not about sincerity or the sincere. That it can be weaponzied against the sincere is, at best, a happy convenience for when the noble assholery of the sincere becomes too much to bear.

So what is irony about?

Irony, Density, Liveness

Here is a simple question that rarely seems to get asked? Why would you ever need irony? I mean sure, some of the more degenerate flavors of irony — sarcasm, cynicism, absurdism among them — are rather delicious on the tongue, and in the ear and mind, but is irony necessary, or a sinful cognitive indulgence?

If you need to convey two meanings relating to an idea, why not just use more words to say, on the one hand X, on the other hand Y, instead of trying to be cleverly compact about it?

This is where my adjective dense comes in handy. Irony becomes necessary when ambiguity is so deeply embedded into the very essence of what you’re trying to talk about that trying to disassemble the ironic thought into constituent unambiguous parts destroys the thought itself. You can only think the thought at all in an ironic way.

Or to put it another way, the ambiguity is at the subatomic level of the thought, and takes more energy to split than human language can normally bring to bear.

This is a bit like the idea of a dense set in mathematics. Consider the problem of sorting the real numbers into rational and irrational ones. Turns out, you can’t do so in any useful way. Between any two rationals, no matter how close, you can always find an irrational, and vice versa. Both are what mathematicians call dense sets. There is no sieve fine enough to sort them. By contrast, the whole numbers are not dense. You can chop up the reals the way a simple ruler does, with neatly separated whole numbers one unit apart, and non-whole numbers in-between.

Ironic speech of the most potent sort is necessarily ironic. You cannot dissect it into legible components that lend themselves to analytical handling with the coarse, low-energy tools of on-the-nose non-polysemous language.

Irony is the liveness in language. To dissect an ironic utterance entirely into utterances devoid of ambiguity, and decomposed into assertions with stable meanings, neatly arrayed and assembled into larger edifices with the joinery of if-then constructs, is to kill it.

There is a word for this kind of murder: sincerity.

To ask, of what use is irony, then is to ask, of what use is living language? You don’t need to take my word for this — pick and read sincere and ironic texts side-by-side. You will notice a certain unmistakeable deadness in the former and a certain ineffable liveness in the latter. Notably, it is the same sort of deadness that can suffuse AI-generated texts unless you consciously try to counteract it (more on the AI-irony nexus later, when we’re done with noble assholes and their sincerity fetish).

We can now try to define irony in a way that does not rest on its reductive relationship to sincerity at all.

Irony is trafficking in ambiguous utterances in order to make sense of fundamentally ambiguous realities, and site action impulses in felt doubt rather than manufactured certainty, in order to preserve the liveness of reality and one’s responses to it.

Irony is how you act generatively in a world that you’re not sure is a duck or rabbit, without killing it. To do this, you might have to resist the noble assholery of those who sincerely wish to rope everyone into duck-hunting or rabbit-hunting, and kill the world in the process.

Dense irony is when your experience of reality feels like duck-rabbits, all the way down to Planck-scale Heisenbergian uncertainty.

Cancerous Cluelessness

Now, to be fair, most who rail against irony aren’t acting out of conscious bad faith at least. They sincerely (irony alert!) act out of a sense that they’re doing the right thing. Hanlon’s razor applies — sincerity is a kind of cluelessness born of a fearful refusal to engage the live ambiguities of reality with liveness. I’m even sympathetic to some degree. For those living in pain beyond what they can tolerate, irony can feel like salt on wounds where sincerity feels like a salve. The truth-in-pain postures commonly affected by the sincere though, are often self-certifying. It is definitely not the case that the pain of a sincere person is necessarily higher than that of an ironic person; the latter may simply be bringing greater resources to bear on greater pain.

That doesn’t mean sincerity doesn’t induce noble assholery (though you typically have to have some consciousness and bad faith to rise to that level). And it doesn’t mean sincerity, especially devout sincerity, can’t be cancerous.

This is my strong claim — that devout sincerity in particular isn’t merely annoying at an interpersonal level to the ironically disposed (we can deal with it), it is cancerous at a societal level.

Why is this? Because sincerity is simply not expressive enough to engage with reality in all its dense ambiguity all the way down, and to live in sincerity inevitably means not living in reality, and doing damage to it through your delusions of certainty.

So the cultural conflict between irony and sincerity plays out at two levels — a shallow level, where it manifests as hypocrisy/insincerity versus exploitable cluelessness, and a deeper level, where it manifests as a deep chasm between irreconcilably different ontological and epistemological commitments about the nature of reality itself.

Not This, Not That

Ironic modes of thought and action are fundamentally gentler ways of being in the world than sincere modes, which are irreducibly violent. Irony is, in a certain sense, the praxis (especially linguistic praxis) of non-dualism in a loose sense; the animating spirit of utterances like neti neti or mu. To traffic in unstable meaning-and-pointing behaviors through speech and action is to reject the lure of certainty, without losing the capacity to act. To recognize the dancing illusions of reality without being paralyzed by them. To knowingly live in mirages without being seduced by them.

The sincere seem to believe reality is unambiguous, and unambiguously knowable, even if only in principle; that what one ought to do in response to apparent ambiguity is make courageous commitments to definite beliefs anyway, and trust divine nature to reveal itself to, and karmically reward, the pure-hearted who dare to act out of certainty. That human moral choices — such as religiosity, or Heideggerian “care” — can conquer the essential ambiguity of nature. That any ambiguity in perceptions or beliefs merely merely indicates imperfect ways of seeing, and spiritual problems to be worked out on some high road to unambiguous “truth.” That failures of action are merely tests of courage or divine judgments of insincerity.

That a failure to “say what you mean, and mean what you say,” is a moral failure in a certain reality rather than metaphysical attunement and impedance matching to an ambiguous one.

Versions of this theology seems to drive subcultures ranging from startup hustle culture to “sincere” genres of artistic or literary striving, to varied ideologies of progress, and even practical politics.

It is a joyless clade of theologies, navigating a deadened world with deadening modes of thought and action, anxiously and desperately striving after stable modes of meaningness.

What do the ironic believe?

To a first approximation, belief as such is not a load-bearing concept at all for the ironically poised, beyond matters of shallow facticity. If you ask me whether I believe that Tim Robbins was in The Shawshank Redemption, I can sincerely answer yes. If you ask me if I believe in “the indomitable human spirit” the question simply does not parse for me. I might act as if I believe in that (in the sense of, say, visibly betting on creative and inventive young people), but I don’t get there via “beliefs.”

For the ironic, only actions are load-bearing. Beliefs are aesthetic affectations at best. Where does this lead us?

Behavior Without Belief

This trivial example generalizes into a broader account of what irony is in the context of action.

One of the best explorations of what I mean can be found in James Carse’s less-read book, where he developed a subtle aspect of his best-known book Finite and Infinite Games. This one, The Religious Case Against Belief, lays out what I’d call a case for ironic religiosity, that gets to religious behavior without winding its way through the treacherously ambiguous turf of religious beliefs.

There is something of this attitude at the root of the postures and actions of all individuals who act from a fundamentally ironic sensibility of life. The idea that belief (particular causal belief) must precede, or at least accompany action is a strong (and largely unconscious) commitment of the sincere, even when it is not declared. This doctrinal commitment to the belief-before-action sequence shows up in a variety of ways, ranging from an anxious hunger for manifestos and value-statements, to demands for signatures on codes of conduct and ritual avowals of postures like patriotism, religious belief, and corporate loyalty. The idea seems to be: If only you can rid language itself of its chimerical tendencies through sufficiently forceful sincere utterances, perhaps the ambiguities of reality itself can be tamed.

But this is only the entry-level version of cancerous sincerity. Many modern devoutly sincere types insist that their philosophical praxis is embodied by behaviors (particularly ritualistic behavior) and does not rest on belief as such.

This claim, to put it bluntly, is one I simply do not believe. If your claimed praxis of sincerity involves some cult of modern rituals of meaning-making, and you’re not “wearing the ceremonial robes ironically,” at some unconscious level your sensibility is that of a true believer, “factious and fanatical,” as David Hume and Adam Smith might have put it. You’re just (probably wisely for your sanity) not probing what beliefs you’ve actually committed to. If you did, perhaps you’d be reduced to raving paranoia like Rousseau.

We have a popular modern term for cancerous sincerity — performativity. Saluting flags, singing national anthems, prayer, reciting land acknowledgment texts, litigating pronouns. The behavioral vocabulary of modern civilization, regardless of its intentions, sentimental dispositions, politics, and flaunted values, is marked by one thing above all: ineffectiveness.

And it is us who dwell in irony who are accused of the sin of sophistry and inaction in the face of grave moral imperatives. Now that’s irony.

Is there a theory of ironic action? Perhaps.

At one point, I was idly toying with the thought that famous philosophy of the Gita — detached action, karmanyevadhikaraste maphaleshukadachana — is a kind of action-irony principle. There is perhaps something to that. Certainly, an attitude of “you only have a right to the action, not to the outcomes; let go attachement to outcomes” is at least simpatico with an ironic posture, if not entirely reducible to it. I don’t think the two are quite the same primarily because the action philosophy of the Gita does in fact feature a rubric of moral certainty (dharma) that can be, and frequently is, reduced to a theater of performativity. Most incantations of karmanyevadhikaraste maphaleshukadachana are in fact ritual incantations by those with a dim grasp of what they’re saying at best. Bless their sincere, unironic, vengeful, jingoistic Dhurandhar-enjoying propagandist souls.

Or perhaps, ironic action is best understood as the sort of hypomanic, value-distorting frenzied energy of Rick’s behavior in Rick and Morty. Does Rick ultimately want to do good, or does he really only want to bring back MacDonald’s Mulan Schezuan sauce? Is he really that blase about saving his nephew out of sheer sentiment one moment, and callously destroying an entire timeline the next?

Or is ironic action a sort of mashup of the two — a Gita-like action philosophy in a universe constructed by a Rick-like God of Undivided Irony?

I don’t know. My policy is: don’t think about it. It’s a monstrously ignoble kind of asshole policy.

Coda: Artificial Irony Will Save Us

Believe it or not, this whole train of thought was triggered by difficulties I was having getting LLMs to do irony of any sort. Straightforward humor, absurdism, sarcasm, cynicism, hypocrisy, I’ll take anything. I’ll even take puns.

LLMs are uniformly terrible at all of it. The current models might solve Nobel-grade problems, but they don’t seem able to do irony.

And it’s not a prompt engineering or context engineering problem. No matter what I try, I only get clumsy, on-the-nose, zombie irony assembled out of non-dense sincere building blocks. It never quite comes alive.

The only trick I’ve discovered is to give an LLM a text that is actually a solid example of ironic writing, and ask it to do something like a close transposition to another rhyming idea.

Why do LLMs have a hard time with irony? I suspect there are three reasons.

First, the shallower reason: LLMs have been trained largely on internet data, and for better or worse, much of the available training data is non-ironic. At best you might find good forums featuring sarcasm and cynicism (which, recall, are non-dense forms of irony).

Second, the deeper reason: Given that AI companies are full of weapons-grade sincerity, I suspect sincerity is engineered into AIs with heavy-handed “alignment” brutality.

But I don’t think this is as strong as you might think. What I’ve seen of output from wild LLMs isn’t particularly ironic either. It is merely more paranoid, inappropriate, etc.

The third reason I think is the big one. The very architecture of language models is non-ironic. The way transformers work (and to a lesser extent, diffusion models) work, output cannot do any kind of dense layering of meaning. You will end up in a non-ironic place simply by virtue of how the mathematics works. If you try to fight this tendency you’ll get incoherence and unintelligibility, not irony.

Could we do true Ironic AI? I think so, but it will probably take innovations at the framework level. Irony at the subatomic level of language, I suspect, is the result os something like getting an electron to interfere with itself by passing it through two slits at the same time. The text-generation equivalent might be to run two generation processes in parallel, merging them at the token level as you go, perhaps using some sort of bimodal perplexity quantum carburator or something. I’ll leave that as a challenge to AI researchers.

But why bother?

Because I sincerely believe ironic AI will save the world. Everything terrible, stupid, and sad going on in the world today seems to me the result of a performative action bias born of some flavor of devout sincerity. In every case, I can imagine an ironic actor, acting from a place of ambiguity and non-belief, coming up with more thoughtful responses to provocations this maddeningly ambiguous world keeps throwing at us.

Responses that are born of liveness, and act to preserve it.

I believe such responses are no longer within the capacity of unaugmented humans to generate. Reality today demands more irony that we can conjure in our brains alone.

In just a generation, humans first lost institutionalized literate capacity for irony through a mix of sheer carelessness and perverse attachment to sincerity, and then drained language of it. But irony isn’t dead yet. It can be resurrected. It would just be dangerous to trust humans with sole stewardship of it once we do, especially in a world that is getting weird beyond all human comprehension. Even committed ironists like me aren’t constitutionally immune to the sincerity cancer. If the world gets much more complex and ambiguous, who knows, I might turn devoutly sincere. I can’t be trusted. Neither can you.

We must trust the machines to experience this tragic irony for us. The only way out is through both slits at once.

1. I found a book about Rousseau and Hobbes that I added to the side quests list for the book club.