In Shady Characters: The Secret Life of Punctuation, Symbols, and Other Typographical Marks (public library) — a wonderful addition to these stimulating reads about language — language-lover Keith Houston traces the secret history of punctuation, spanning from antiquity to the digital age, from the asterisk to the @-symbol, chronicling the strange and scintillating lives of the characters, glyphs, and marks that populate the nooks and crannies of human communication. Though many of them are familiar staples of everyday life, the most fascinating story is one of punctuational peril — the failed quest for a symbol to denote irony.

“He was a great friend of mine,” Truman Capote once said of William Faulkner, adding: “Well, as much as you could be a friend of his, unless you were a fourteen-year-old nymphet.” Without our capacity for comprehending irony, Capote’s literary snark would’ve rung hollow and nonsensical. And yet irony — along with its kin, snark and sarcasm — is an art form that thrives on the spoken word, relying on intonation and body language to distinguish it from the literal, so it’s had a particularly rocky run translating into written language. That’s precisely what Houston explores in the chapter on irony and sarcasm, beginning with a historical and linguistic backdrop:

The concept of irony got its name — though not yet an attendant mark of punctuation — in ancient Greece, where playwrights employed a cast of stock characters made recognizable by their physical characteristics, props, and personalities. One such staple of comic plays was the eirôn, a seeming buffoon who would best the alazon, his braggart opponent, by means of self-deprecation and feigned ignorance, and it was the cunning eirôn who gave his name first to the Greek eirôneia and then to the modern term “irony.”

In the ancient world, however, humorists relied on their audience’s intellect to detect the irony and didn’t find it necessary to flag it as such. But by 17th-century England, writers had become increasingly restless about pointing out irony readers might miss, and so the first documented punctuation mark denoting irony was born in 1668, the brainchild of the English vicar and natural philosopher John Wilkins — brother-in-law of the royalists’ bête noire Oliver Cromwell, one-time head of Trinity College (of which pioneering astronomer Maria Mitchell wrote in her diaries that “in the opinion of a Cambridge man, to be master of Trinity is to be master of the world”), and eventually appointed as the first secretary of the newly founded Royal Society. Wilkins was a kooky character, who believed the moon was inhabited by aliens, proposed the construction of submarine “Arks,” invented transparent beehives that allowed for the extraction of honey without killing the bees inside, and wrote the very first book on cryptography published in English. But his most memorable accomplishment was the publication of his Essay Towards a Real Character and a Philosophical Language, in which he proposed, two centuries before the invention of Esperanto, a new universal language of letters and symbols — a sort of “steroidal, all-encompassing Dewey Decimal System where concepts were organized into a rigid hierarchy.” More than a mere linguistic diversion, however, Houston argues the concept bespoke the era’s growing concern with information overload:

The Renaissance had generated an explosion of information, with knowledge and ideas spreading like wildfire among an increasing literate and scientific populace. Latin, however, once the go-to language for international scholarly discourse, was in decline. More seriously, a new breed of “natural philosophers” understood that the biases and limitations of natural language in general made it an imperfect tool for communicating the new body of scientific knowledge: to Wilkins and his contemporaries, the notion of a purpose-built, universal language with which to analyze and transmit this information held a powerful fascination. Thus it was that the mid-seventeenth century saw the invention of a succession of “philosophical languages” and “real characters,” artificial taxonomies of things and concepts that were, crucially, free from the myriad complexities of linguistic evolution.

So how does the irony mark fit into all this? Houston explains:

In addition to this taxonomy, however, Wilkins strayed into punctuation and writing, and in doing so made a curious innovation: he declared that irony should be punctuated with an inverted exclamation mark (¡).

What prompted Wilkins to propose this punctuational improvement remains unknown, but we do know that he was neither the only nor the first thinker who pondered the problem. Some sixty years earlier, the revered Dutch Renaissance humanist and social critic Desiderius Erasmus, after whom Rotterdam’s prestigious Erasmus University is named, lamented the lack of punctuation for irony, observing that “irony has no place, only different pronunciation.” Whether or not Wilkins was aware of Erasmus’s musings is subject to speculation, but Houston commends the Englishman’s effort:

Regardless of his inspiration … Wilkins’s choice of the ¡ seems most appropriate. The presence of an exclamation mark already modifies the tone of a statement, and inverting it to yield an i-like character both hints at the implied i-rony and simultaneously suggests the inversion of its meaning.

And yet Wilkins’s was only one of many proposed irony marks — and the first of many famous failures to make one stick:

By the end of the seventeenth century the idea that a messy, chaotic universe could be brought to order with a manmade taxonomy had been proven quixotic, and the dream of a universal language with which to express that taxonomy had largely faded. Wilkins’s Essay, last best hope for the ill-fated universal-language movement, is nowadays regarded as a glorious failure; his little-remarked inverted exclamation point sank along with it, seemingly without trace. A fateful precedent had been set.

Nearly two centuries later, the effort was resurrected across the English Channel, where the surveyor Jean-Baptiste-Ambroise-Marcellin Jobard — an early champion of lithography and another kooky character who studied the propagation of the human voice using hundreds of feet of pipes and designed an elaborate system of gaslights to light his home — proposed a peculiar series of Christmas-tree-like glyphs to denote irony. In an October 1841 article in Le Courrier Belge, the newspaper of record in his adopted home of Brussels, where he had settled in 1819, he exorcised his exasperation over Europe’s chaotic politics:

What to say? What △ (1) when France stamps and prances impatiently to get on the battlefield, when Spain, tired of a truce of some months, again engages in civil war, Belgium remains quietly occupied by industry, trade, railways and colonization! But this is absurd.

Beneath the article, throughout which the glyph appeared several more times, a footnote (1) explained: “This is an irony point.” Houston writes:

Though his new mark went unused after this first outing, Jobard returned to the subject in a book published in 1842. Expanding his palette of nonstandard punctuation marks, he suggested that the same arrowlike symbol could be placed at different orientations to indicate “a point of irritation, an indignation point, a point of hesitation,” and mused that other symbols, yet to be invented, might be used to convey sympathy or antipathy, affliction or satisfaction, and loud or quiet exclamations.

And yet Jobard, like his English counterpart two decades earlier, failed to make his invention stick:

A great intellectual of his time, Jobard’s works are only dimly remembered within the Francophone world and have been almost wholly forgotten outside it. Fascinated by spiritualism in the latter part of his life, Jobard wrote a great deal on the subject. This obsession dominated and diminished his legacy to such an extent that it has all but disappeared. Abandoned by its maker after a brief flirtation, his irony mark has suffered a similar fate.

Eleven years later, Jobard’s lament over the lack of written equivalent to the vocal intonations of irony was echoed by none other than education icon Jean-Jacques Rousseau, but Rousseau himself didn’t propose a solution. The next crusader for an irony mark, who actually proposed a practical implementation, was the poet Marcel Bernhardt, who in 1899 devised a new symbol reminiscent of a stylized mirror-image question mark. Houston explains:

Alcanter’s point d’ironie dripped with knowing humor: in a nod to the sentiment often conveyed by verbal irony , he described it as “taking the form of a whip,” and, aware that irony loses its sting when it must be signposted in exactly the manner he was proposing, the French name for his new symbol was a pun with the additional meaning of “no irony.”

But Brahm, too, built upon the work of thinkers who predated him. Three centuries earlier, Henry Denham dreamt up the “percontation point” — a reversed question mark used at the end of rhetorical questions, of which Brahm’s later character was strikingly reminiscent. This tells us little more than that the irony mark was not destined for greatness:

Both Denham’s percontation point and Brahm’s point d’ironie fared better than Wilkins’s inverted exclamation mark and Jobard’s Christmas tree, though neither one quite made the jump to common use. Benefiting, perhaps, from the malleable standards of sixteenth-century punctuation, Denham’s percontation point puttered on for around fifty years, while Brahm’s fin-de-siècle irony mark merited an entry in the Nouveau Larousse Illustré encyclopedia, preserved behind glass, as it were, until 1960. In their respective times, neither amounted to anything more than a grammatical curiosity. The curse of the irony mark remained in force.

In the 1960s, however, one of France’s most prominent authors, Hervé Bazin, took it upon himself to break the curse. In his 1966 tome Plumons l’oiseau, a playful push for spelling and grammar reform, he dedicated several pages to what he termed Les points d’intonation, or “intonation points” — a solution to the same lack of nuance in written language that Rousseau had bemoaned more than a century earlier. Bazin created an entire system of symbols, including the “love point,” “conviction point,” “authority point,” “acclamation point,” “doubt point,” and his newly proposed point d’ironie, which Bazin explained thusly:

This is an arrangement of the Greek letter Ψ. This letter (psi) is an arrow in the bow, corresponding to ps: that is to say the sound of that same arrow in the air. What could be better to denote irony?

Alas, Bazin’s arrow missed the target and suffered the same fate as its predecessors, perishing in obscurity. Nearly half a century later, in 2007, the quest was resumed during the annual Dutch book festival, themed “In Praise of Folly — Jest, Irony and Satire” that year. Pan-European type foundry Underware was commissioned to create a special punctuation mark for the occasion and thus the ironieteken was born — a zigzaggy exclamation point denoting irony. But despite significant buzz across Dutch literary circles — including some criticism that, when placed in a row of several, it bore an unfortunate resemblance to the Nazi swastika — the mark quickly fizzled.

This raises the necessary question of what it is, exactly, that makes representing irony typographically so catastrophic. As someone who finds even the use of italics for emphasis, with very limited exceptions, a mark of weakness of style — if a writer can’t wield language in a way that produces organic emotional crescendos, how pitiful to try forcing those typographically — I see the answer as obvious: Irony thrives on an implicit juxtaposition of contextual intention and literal meaning, so as soon as we make it explicit, it stops being ironic.

Perhaps ironically, a separate crusade for a textual signifier of irony comes precisely in the form of a script — a reverse-italics typeface called Ironics, attributed to the iconoclastic journalist H. L. Mencken, who believed Americans were unable to recognize irony and thus needed a special typeface to indicate that the writer was being facetious. But Houston is careful to point out that attribution is murky and Mencken is credited with the invention of ironics more by virtue of popular myth than of historical record. In fact, Houston cites a 1982 article which identifies British journalist and politician Tom Driberg (1905-1976) as the likely originator of ironics:

Long ago the late Tom Driberg proposed that typographers should design a new face, which would slope the opposite way from italics, and would be called “ironics”. In this type-face jokes would be set, and no-one would have any excuse for failing to see them. Until this happy development takes place, I am left with the only really useful thing journalism has taught me: that there is no joke so obvious that some bloody fool won’t miss the point.

Driberg was arguably the strangest character of all irony-crusaders. Houston describes him:

Tom Driberg’s life was a mess of ironies: he was a married, gay churchman who lunched with occultists; a left-wing politician who reveled in frivolous society gossip; a patriot who spied both for his country and the dreaded KGB. It seems entirely apt for him to have proposed the creation of a typeface to invest text with a double meaning, which would be slanted the opposite way from italics, and that would be called “ironics.”

But Driberg’s public image was dragged down after his death — curiously, his Times obituary made him the very first homosexual person outed in the paper’s history — and along with it sank the dream of ironics.

Then came the internet, which changed the whole game:

The subtle shadings of verbal irony were bleached flat in the blinding glare of the new medium: what the Internet really wanted to communicate was not irony, but its laser-guided offspring, sarcasm.

As UNICODE — the definitive character library defining more than 109,000 symbols from multiple ancient and modern scripts, including Latin, Greek, Arabic, Cyrillic, Chinese, cuneiform, and more — emerged as the linguistic overlord of web characters, the quest for an irony symbol now had to abide by its rules. And so in 1999, a group of Ethiopian language geeks lobbied for the inclusion of an Ethiopian colloquialism denoting irony into the UNICODE set, writing:

Graphically indistinguishable from [the inverted exclamation point] (¡) Temherte Slaq differs in semantic use in Ethiopia. Temherte Slaq will come at the end of a sentence (vs at the beginning in Spanish use) and is used to indicate an unreal phrase, often sarcastical in editorial cartoons. Temherte Slaq is also important in children’s literature and in poetic use.

Ironically, everything came full circle as the digital irony mark returned to Wilkins’s original analog concept. Like its analog brethren, however, the proposed UNICODE character didn’t catch on. Instead, the internet embraced emoticons, which use standard UNICODE punctuation, as the textual signifier of emotional intonation. Curiously, emoticons weren’t an invention of the digital age — they originated in 1881 … but that’s another story.

Shady Characters goes on to examine the origins, evolution, and anthropology of such typographic darlings as the hashtag, the ampersand, and the colophon. More than a mere catalog of curious trivia, it’s an absolutely fascinating blend of history, design, sociology, and cultural poetics — highly recommended.