If the multiplicity of irony marks created over the centuries suggests anything, it is that irony must be peculiarly tricky to communicate in writing. And if the subsequent failure of each and every one of those marks to gain anything approaching mainstream acceptance is anything to go by, it is unlikely to get any easier.

Irony is, at its heart, the presence of a second, contradictory meaning within a situation or expression. Dictionary definitions1 vary in the details, but all broadly agree on its main flavours.2 Socratic irony, for instance, is the use of feigned ignorance of the subject at hand — the way a teacher answers a student’s question with another question, or a skilled debater gives his opponent enough rope to hang himself. In dramatic irony, the audience of a dramatic work is made aware of the true state of affairs while one or more of the characters are not; Romeo’s despairing suicide in response to Juliet’s apparent death, which the audience knows to be faked, is an oft-quoted example. Situational irony describes an occasion or event whose outcome is opposite but perversely appropriate to what was expected, while its sibling cosmic irony sees a guiding hand behind such occurrences. When someone mutters “Isn’t that ironic?” they are almost certainly referring to a perceived situational irony.

In all these cases, the power to decide whether or not a given situation is ironic lies in the hands of its observers. Ironies like these simply are, or are not; they neither benefit from nor require punctuation.

Verbal irony, by contrast, the simple act of saying one thing while meaning something else, presents ample opportunity for both the ironist and their audience to get it wrong. This form of irony in particular is a staple fixture of modern communication: a study of conversations between American college students in 2000 found that verbal irony (along with its brattish stepchildren sarcasm, hyperbole and understatement) accounted for fully 8% of their conversational turns.4 Despite lending itself well to the nuances and inflections of the spoken word, committing verbal irony to paper is fraught with difficulty for both writer and reader, demanding a certain amount of skill on the part of the would-be ironist and an associated degree of perceptiveness of its audience. As such, it is the written presentation of verbal irony that has attracted the attention of a string of writers, academics, journalists and typographers bent on ‘fixing’ its shortcomings.

The first documented attempt to create a mark intended specifically to indicate an ironic statement came more than three centuries ago, when the English vicar and natural philosopher John Wilkins published his Essay towards a Real Character and a Philosophical Language in 1668.5 Brother-in-law of Oliver Cromwell, first secretary of the newly-founded Royal Society, head of Wadham College, Oxford and later Trinity College, Cambridge,6 Wilkins was a minor Leonardo da Vinci of his day: among other enterprises, he posited the possibility of extraterrestrial life on the moon7 (and designed a flying machine to get there8), wrote the first book on cryptography in English, and fabricated transparent beehives that allowed honey to be extracted without killing the bees inside.9 Essay, though, was to be his crowning achievement.

Delayed by the partial destruction of his manuscript in the Great Fire of London of 1666,10 Wilkins pressed on to publish the book two years later. Essay was a bold, bipartite endeavour: the ‘real character’ of the title was Wilkins’ proposed taxonomy of letters and symbols intended for “the distinct expression of all things and notions that fall under discourse”,11 while the corresponding ‘philosophical language’ was a phonetic guide to pronouncing the resultant terms.

Wilkins declared that within his constructed language, irony should be punctuated with an inverted exclamation mark (‘¡’).12 Like Ray Tomlinson’s selection of the ‘@’ symbol for his new email addressing scheme, with hindsight Wilkins’ choice of the ‘¡’ seems most appropriate. The exclamation mark already modifies the tone of a statement, and inverting it to yield an ‘i’-like character both hints at the implied irony and suggests the inversion of its meaning. Unfortunately, apt as his decision may have been, Wilkins’ invention has the distinction not only of being the first of many irony marks but also the first to fail. Essay is nowadays regarded as a glorious failure, a grand but ultimately doomed attempt to impose order on the intrinsic disorder of the universe. His irony mark sank along with it, seemingly without trace, and the prospect of a dedicated irony mark went unaddressed for two hundred years afterwards.

The next stirrings towards an irony mark came in 1781, when the Genevois philosopher Jean-Jacques Rousseau complained in his Essai sur l’origine des langues ,13 (‘Essay on the origin of language’) that the vocal inflections that so readily identify an ironic statement are absent from its written representation. This lack of punctuation for irony seemed to hold a particular fascination for Francophones, for after Rousseau’s musings the next two attempts to remedy it would come from prominent French writers.

The poet Marcel Bernhardt — better known by his anagrammatic pseudonym Alcanter de Brahm — was first to throw his chapeau into the ring. His 1899 book L’ostensoir des ironies 14 (‘The Monstrosity of Irony’) was a meandering philosophical tract in which he put forward a new mark of punctuation resembling a stylised, reversed question mark. Alcanter’s point d’ironie, or ‘irony point’, was dripping in knowing humour. In a nod to the sentiment often conveyed by verbal irony, he described it as “taking the form of a whip”,15 and, aware that irony loses its sting if it must be telegraphed in exactly the manner he was proposing, the French name for his new symbol was a double entendre with the additional meaning of ‘no irony’.16

Wayne C. Booth, Professor Emeritus of English at the University of Chicago until his death in 2005, addressed de Brahm’s irony mark in the dense 1974 tome A Rhetoric of Irony . At first dismissing the point d’ironie as reducing the value of irony (de Brahm himself would have been first to acknowledge the limitations of his creation), Booth goes on to make the insidious suggestion that any reader encountering such a mark would be faced with a dilemma: does the mark genuinely signal an ironic statement, or is the mark itself being used ironically?17 Later, though, when discussing the variable degrees of success with which irony is deployed in literature, he drops in an ironic footnote of his own:

If [de Brahm] had ever developed his system he would surely have wanted a set of evaluative sub-symbols: * = average; † = superior; ‡ = not so good; § = marvelous; || = perhaps expunge.18

Unsurprisingly, Booth’s tongue-in-cheek ‘evaluative sub-symbols’ never went further than the pages of his book.

Perhaps unwittingly, Alcanter de Brahm had created a mark of punctuation that was uncannily similar in both form and function to a much earlier one. As far back as 1575, the printer Henry Denham had so doubted the acuity of his readers that he had felt it necessary to create the ‘percontation point’, a reversed question mark (⸮) used to terminate rhetorical questions.19 By taking it upon himself to furnish this subspecies of verbal irony with a unique mark of punctuation, Denham prefigured Alcanter’s own irony mark by three centuries.

Both Denham’s percontation point and de Brahm’s point d’ironie fared better than Wilkins’ inverted exclamation mark, though neither one managed the jump to common usage. Benefiting, perhaps, from the era’s still-malleable standards of punctuation, the percontation point soldiered on for fifty years before disappearing, while the point d’ironie merited an entry in the Nouveau Larousse Illustré encyclopaedia and its successors until 1960.15 In their respective times, neither amounted to anything more than a grammatical curiosity.

A few years after the whip-like point d’ironie appeared in the pages of Le Petit Larousse Illustré for the last time, one of France’s best-known authors revived the search for an irony mark with his own suggestion. And a mere suggestion it was, right from the very start: best known for novels of familial strife and youthful rebellion, Hervé Bazin adopted instead a distinctly playful tone for 1966’s Plumons l’oiseau: divertissement or ‘Plucking the Bird: a Diversion’. Born in Angers in 1911 to a strictly Catholic family,20 Jean Pierre Marie Hervé-Bazin railed against the strictures of bourgeois life from a young age, running away several times and generally doing his level best to infuriate his overbearing mother. The feud spilled over into his breakthrough 1948 novel Vipère au poing ,21 or ‘Viper in the Fist’, in which he fictionalised the struggles of his childhood — the novel features a domineering mother named Folcoche, from the French folle for ‘crazy’ and cochonne for ‘pig’ — to great critical acclaim and not a little scandal.

By 1966 the firebrand writer had calmed somewhat, and Plumons l’oiseau was a gentle foray into spelling and grammar reform. Among discourses on the irrationality of modern French, descriptions of a proposed phonetic spelling system (‘l’orthographie lojike’) and sundry grammatical changes, Bazin found time to pen a few pages on what he called Les points d’intonation,22 or ‘intonation points’. Like Rousseau, he contended that written language lacked the nuance and subtlety of the spoken word; unlike Rousseau, he rolled up his sleeves and addressed the problem by creating a whole range of new punctuation marks. In addition to the ‘love point’, ‘conviction point’, ‘authority point’, ‘acclamation point’ and ‘doubt point’ was Bazin’s own point d’ironie:

Bazin explained his new mark thus:

Le point d’ironie: ψ 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?23

Despite this picturesque explanation, and like Wilkins’ and Alcanter’s efforts before it, Bazin’s mark was doomed to obscurity. His point d’ironie was the last ‘analogue’ irony mark: the future resurrection of the idea would come not from traditional authors but instead the collaborative drive of that engine of relentlessly ironic discourse, the Internet.