How Did X Become the Edgiest Letter?

From holiest hallmark to horniest sex symbol — the X-treme, X-haustive story of how the wild child of the alphabet lost its way

It’s perhaps not pornography’s fault that it’s cashing in on a global crisis. As, around the world, whole societies confine themselves to their quarters, traffic to major porn sites has been spiking everywhere, telling us all we need to know about how humans with a broadband connection tend to deal with exceptional levels of boredom and anxiety. From the point-of-view of page views, the season of self-isolation might well be the porn industry’s historical high point — but in terms of reputational damage, it also marks a new low for one of Western culture’s most enigmatic figures.

Once, the letter X was the holiest of all alphabetic symbols, standing for nothing less than the triumph of Christendom itself. The Roman emperor Constantine I imposed his adopted religion on Europe and the Middle East, with armies marching under the banner of an “X,” and for centuries, Latin scribes used it as shorthand for “Christ.” But at the present moment, the worldwide glut in logging on to jerk off means that more people than ever are being exposed to the vice-addled cipher it’s now become — from XVideos to XHamster and from XTube to Pornhub’s search-result enticements to watch “Hardcore XXX sex clips & adult porn videos,” these days, the 24th letter of the English alphabet is synonymous not even with professionally lit kissy porn, but rather the explicitier, extremier world of hardcore sharing platforms.

It’s a remarkably stratospheric fall from grace, especially for such a shy and retiring character — X is the second-least-common letter in written English (after Z), and the one that begins by far the fewest number of words. Oh X, what happened to you? Where did it all go so badly wrong that you’re hanging out in NSFW corners of the internet, bathed in neon and hustling for credit-card details?

For definitive answers to this vexing question, I initially thought to consult the acknowledged world-leading experts on this sort of thing. But all Sesame Street had on offensive and gratuitous X-branding was this:

So instead I turned to the next best available authority: A brand-savvy public relations agency for the adult-entertainment industry, Adult PR. According to Managing Director Sarah (who was a little wary about giving her last name — let’s call her Sarah X), the letter X’s inexorable slide into disrepute has gotten to the point that even the world of pornography is beginning to turn its back on it. “Its popularity has continued over the last four decades and become a staple of adult branding,” she says. But now, “I definitely think it’s a trend that’s reducing. People are trying to be a little more adventurous and move away from what everyone else in the industry is doing.” 

According to Sarah, modern X’s close association with the adult industry is a direct result of the MPAA’s introduction in 1968 of audience-advisory ratings for movies — where the classification “R” stood for “restricted” and “X” for extreme. In the 1970s, “to differentiate [their movies] from mainstream films that had been rated for viewers ages 17 and over,” says Sarah, porn marketeers co-opted the X rating to signal erotic content on their posters and packaging, and “started using it to scale the ‘steaminess’ of their films — with ‘X’ being hot and ‘XXX’ being super naughty in adult-film terms.”

The association of the letter with a certain class of obscene material was ultimately made official in 2011, when the Internet Corporation for Assigned Names and Numbers approved the top-level domain of “.xxx” for release, in an effort to give pornography its own online play area away from the .coms and .orgs of safe-for-work browsing. Though it hasn’t had a great deal of adoption, the .xxx domain was actually the result of 10 years of heated debate among the various registrars and authorities who police domain-name registration, which is an awful lot of cross talk.

That aside, today, the triple-X device remains a straightforward sell for a mass online audience. But as Sarah explains, the real climax for loud-and-proud X-branding in pornography came way back in the 1980s and 1990s. As far as switched-on insiders like Adult PR are concerned, Xed-up content these days has overly strong associations with the “boys’ club” mentality of that era. Or, to put it another way, using X’s nowadays is a throwback that places too heavy an accent on the X-ploitative side of adult entertainment.

If her agency is called upon to consult on marketing with a start-up, says Sarah, “We would advise adult brands to avoid the ‘X’ theme. For us, the ‘XXX’ branding is extremely dated and very male-focused. That’s not to say it won’t work for brands. If you’re looking to target an older male audience, this will help transport them back to their heyday.” For that reason, and as the adult business progresses toward a more inclusive, female-friendly industry, she says, “We believe it should be left in the porn section of old-school video shops.”

X is for Salvation and Damnation

It was Hollywood, in that case, in the guise of the MPAA, who corrupted X and pimped it out to porn. Notice that the movie regulators didn’t use “E” to designate “extreme” or “explicit” content, though. Back then it might not have built up the illicit connotations it has today, but by the 1960s, the moral status of X was already compromised and its mystique had long been established as an ambiguous, not-quite-right (and often just-plain-wrong) semiotic entity.

In 2015, Iain Collins, an English lecturer who at the time worked at Saudi Arabia’s Prince Mohammad Bin Fahd University, gave a TEDx talk on “The History and Importance of the Letter X,” choosing the topic partly because of the presence of the rogue “x” in the lecture platform’s branding. (And what does that oddly appended x actually stand for? Don’t ask.) Initially Collins was going to speak about the use of technology in education, but he recalls he “noticed the organizers were advertising the conference with ‘The Power of X,” so I thought I’d look into it. I didn’t realize it would be such a trove of contradictions.”

In his wide-ranging talk, he manages to squeeze in an extravagant amount of cultural associations that have glommed onto the letter throughout its history, while also giving a detailed account of how it first arrived in the Latin alphabet — by way of X’s ancestors in the Etruscan, Western Greek and ultimately Phoenician ancient writing systems. Rummaging through the clutter of meanings, he identifies a recurring theme in which X is often recruited to represent directly opposing ideas: It’s both positive (as in when we use it to check a box or vote) and negative (when an answer is wrong or crossed out); it’s been a symbol of life (in religion) and death (on a bottle of poison); in both the sex trade and the alcohol industry multiple X’s are recognized as a promise of potency and intoxication, whereas in the straight-edge punk movement of the 1980s and 1990s, X’s — sometimes tattooed — signified fans’ radical abstinence from all booze, drugs and cigarettes.

Why the conflicting signals? “Well, the letter is made up of opposite parts mirroring each other,” offers Collins, though he concedes there’s probably much more to it than simple hieroglyphic-like aesthetics. He points out that the dichotomies within X are present in its very earliest appearances in mass communication. In the Book of Ezekiel, God orders His angels to perform an audit on the citizenry of Jerusalem by inscribing the letter taw (which looked like an X in both Phoenician and early Hebrew) on the foreheads of good, Him-fearing Israelites; those without the quality-assurance mark He doth smoteth for their sins. The appearance of X’s in this story, then, meant death for some and salvation for others.

Similarly, X cuts both ways as the sign for Christ. In this role, the written character was actually the Greek letter chi (which is actually not the direct phonetic ancestor of our Latin X, though it looks the same; it’s complicated) combined with rho (which looks like a “P” but is pronounced like an “R” — stick with it…). These represented the first two letters of Χριστός (aka “Christos”), superimposed to form the symbol that looks like a mystical helicopter which still adorns Catholic lecterns and prayer books today. 

This Christogram’s prominence in church iconography is often attributed to a Roman legend from 312 A.D. in which the soon-to-be Constantine the Great received a vision of the chi-rho in the sky, accompanied by the words, “In this sign, you shall conquer.” He dutifully had holy helicopters painted on his soldiers’ shields and, so the fable goes, promptly won the civil war, re-founded the splintered empire and in gratitude legitimized Christianity as its dominant religion.

However the chi-rho achieved brand dominance, it’s an abbreviation that litters later-Roman archaeology and coinage, and in the profane world, a further truncation of Χρ is why we get to call Christmas “Xmas.” “That’s evidently where xxx [meaning] kisses comes from too,” points out Collins, since X came to mean faith and fidelity, which morphed in the Middle Ages into the practice of affirming important documents with crosses and/or “sealing them with a kiss.”

So that’s how X’s positive associations with the Messiah supposedly came about. But once you know X stands for “Christ,” a darker set of meanings also come into play. Visually, it’s hard for many of us not to assume it also has “a connection with the cross and crucifixion” when we see it in Christian contexts, suggests Collins, emphasizing the letter in question as he goes. “And if you imagine someone carrying a cross, it might look like an X. Then [once affixed to it] they die from exhaustion and asphyxiation.”

Plus, of course, for non-Christians, any symbol denoting either “Christ” or “crucifix” can feel loaded with negative vibes. Collins cites a 2007 report in the now-defunct New York Sun claiming that Saudi Arabia’s shadowy Commission for the Promotion of Virtue and Prevention of Vice were considering outlawing the letter X within the kingdom. The article’s hysterical anti-Saudi tone pretty much undermines its quixotic main claim, he says, but he doesn’t completely dismiss the notion that some kind of X-related suspicion might have existed among the clerical authorities. The country “back then was in a number of ways different from today,” he recalls. “I think the mutawa (religious police) have more or less disappeared now. I do remember going to Bahrain and smuggling an Xmas tree back — we were stopped at the border but they weren’t fussed and let us bring it through.” 

X is for Danger and Death

The exceptionalism of X isn’t just down to divine favor — down the centuries, it has accumulated an aura of mystery and obscurity from a host of secular sources, too.

One reason English speakers retain a vestigial wariness toward X is that one of its deepest meanings is wrapped up in otherness. In English, words prefixed with the homophone “ex” tend to retain a sense of the original Greek έξω (ekso), which means “out” or “outside.” Often these imply some sort of irrevocable or unbridgeable exterior — exile, exterminate, execute, extinct, ex-partner — and, as Collins points out, in cultural terms, “It’s probably always cooler and more dangerous to be outside the circle.”

In his book Letter Perfect: The Marvelous History of Our Alphabet from A to Z, David Sacks makes the related point that in Greek, “xenophobia” means “fear of foreigners” — “and no word better displays the alien and forbidding spirit that once belonged to X.” Undoubtedly, some of this menace can be traced back to the letter’s adoption by pirates as part of the skull-and-crossbones motif. Long before its Disneyfication, crossed bones on Jolly Roger insignia was a real pirate fixture, having become a widespread meme among Barbary buccaneers in the early 1700s.

Just in case the piratical connexion between the letter X and overlapping femurs wasn’t clear enough, the publication of Robert Louis Stevenson’s worldwide bestseller in 1882 seared it indelibly into popular culture. Treasure Island doesn’t actually feature the words “X marks the spot,” but Stevenson’s vivid description of the story’s inciting treasure map immortalized the image, and concludes with “three crosses of red ink — two on the north part of the island, one in the south-west, and, beside this last, in the same red ink, and in a small, neat hand, very different from the captain’s tottery characters, these words: ‘Bulk of treasure here.’” The very X’s he had in mind had been marked out by Stevenson himself on a real-life map drawn as a rainy-day distraction for his stepson a year earlier, which is what inspired him to write the novel in the first place. 

By the end of the 19th century, stranger-danger on the high seas broadened to a generalized hazard warning, with the skull-and-crossbones on bottles (first used by apothecaries in the 1850s) becoming a popularly recognized device to signal poison within; until recently, both skull-and-crossbones and a hefty X on orange backgrounds were the standardized safety labeling throughout Europe for toxic and harmful substances. Perhaps an extension of this symbolism, X’s macabre relationship with death is universally understood in the visual language of cartoons, whenever a character’s eyes are replaced by crosses: EDM zombie superstar Deadmau5 and Wes Anderson’s virtuoso death scene in Fantastic Mr. Fox are among the standout self-aware examples of this:

X is for Mystery, Mutants and Math

Sex, danger and death are all very alluring character traits, but what’s really given X its edge in the modern imagination is its trademark evocation of secrecy and mystery. And in this respect, Sesame Street does offer some clues: 

Spy code names of the “Agent X” variety have a much older pedigree than you might have thought. One of the most famous exponents was the so-called XX Committee, a special operations unit set up by the British intelligence service MI5 during World War II. Its job, at which it seemed particularly effective, was to recruit German agents and use them to disrupt the Nazi war effort with misinformation, a ploy that played a crucial role in the success of the D-Day landings. It was often called the “Twenty Committee” because its name implied Roman numerals, but what the two X’s really stood for was the tactic the British were pursuing that has since become synonymous with sophisticated spy networks: The “Double-Cross System” of counter-espionage.

Going back much further, one of the most famous cases of international intrigue in American history is known to posterity as “the XYZ Affair.” In 1797, President John Adams’ efforts to resolve an escalating dispute with France were frustrated by agents of the French foreign minister Talleyrand, who tried to extort money from the U.S. From Paris, the American diplomats sent back indignant reports of Talleyrand’s outrageous bribery demands and brazen disrespect, and in their letters they replaced the names of his intermediaries with the aliases “X,” “Y,” and “Z.”

The two-year naval war with France that followed was no doubt an important historical consequence, but the fact that the scandal was known popularly as “the XYZ Affair” plainly exposes the real origin of the letter X’s deep entanglement in covert operations and clandestine knowledge. For this X we can thank two men in particular: the French 17th-century philosopher and mathematician René Descartes, whose 1637 book La Géométrie significantly advanced the study of algebra, and his hapless printer. According to Sacks, in this work Descartes rewrote standard mathematical notation to make the letters x, y and z stand for variables in his equations — but in his draft copy he had intended that z should always be the geometrician’s first choice, working backwards through the alphabet when subsequent algebraic terms were required. 

The story goes, says Sacks, that “the printer, while typesetting the manuscript, found himself repeatedly running short of letter blocks for Y and Z, [but] still had plenty of X’s, a letter that in French is used far less than Y or Z.” So he wrote to René to ask, for equations that used only one or two variables, “might X be the preferred letter for printing purposes? The great man replied that this was acceptable.”

And from that moment on X, and not Z, became the accepted academic token of the Great Unknown. In 1895, when Wilhelm Roentgen happened upon strange beams of energy that could reveal the inner structure of the human body, he called them X-rays, in explicit homage to Descartes’ nomenclature for the unidentified. Four years prior to that, when another German scientist, Hermann Henking, was looking at firebug testicles under a microscope and noticed one chromosome was behaving differently to the others, he called it the “X element” — later renamed “X chromosome,” and discovered to be one of the two that determine sex in most organisms’ reproduction.

Following his lead, in 1963, when Marvel Comics’ Stan Lee and Jack Kirby were dreaming up a name for a new superhero team whose powers came from an obscure genetic mutation, they uncannily settled on X-Men. In 1952, when Malcolm Little formally joined the Nation of Islam, he changed his name to Malcolm X, which for a member of that group, as he later wrote, “symbolized the true African family name that he never could know.” And in 1970, when the British armed forces needed to describe a payment premium to add into military salaries to account for disruptions they couldn’t hope to quantify, such as foreign deployment and death, they called it “the X-Factor” and unwittingly created a monster.  

Sacks identifies the 1950s and 1960s as roughly the time when X’s power to evoke mystery and enigma crossed over from math and science jargon into culture at large, first via its prevalence in sci-fi B-movies (he cites The X from Outer Space, Strange World of Planet X and X: The Unknown) and then in its adoption by product marketers as the sinister “Brand X” of countless TV commercials:

By the 1990s and early 2000s, X branding was everywhere — designed into the casing on Xboxes, adding grandeur to Apple’s OS X operating system, palindrome-ing across packs of Xanax. Despite its by now X-rated associations, writes Sacks, it had “come roaring into the mainstream, to the extent that it [was] one of the defining letters of the new millennium.” This was thanks in part to the huge success of TV’s spooks-v-aliens epic The X-Files, which managed to combine both classic sci-fi unknowns with espionage subterfuge, and in part to the young demographic cohort that found itself ruling counterculture at the time, fatefully identified as Generation X.

This term was coined in 1991 by the title of Douglas Coupland’s zeitgeist-capturing novel, identifying those born in the 1960s and 1970s as vaguely slacker, vaguely nihilistic social enigmas who were vaguely lost in postmodern culture, and it played on the hollowed-out emptiness the letter had by now acquired, as much as on its dangerous mystique. “X as in Brand X,” explained the L.A. Times in 1999. “X as in the anonymous signature of an illiterate. X as in a random variable.” And, of course, as in excellent.

As Sacks puts it, at “the end of the 1960s, X could mean either ‘mystery,’ ‘danger’ or ‘sex’ — a memorable combination.” But by the 2010s, sharing the fate of all cultural artifacts that have a marketable edge, it had been mined to exhaustion by commerce and its scariness and mystique had all but gone. Now that it’s become too cliché-laden and worn down by successive Vin Diesel sequels even to take a starring role in porn, perhaps it’s time that X excused itself from the spotlight for a while. Maybe it should step away from the extreme behavior and excessive lifestyle, exorcise its demons with a spell in rehab, maybe reconnect with that straight-edge phase it went through a while back, and get itself clean enough for Generations Y and Z to put it to good use — perhaps fronting a new line in healthy xalads or wholesome vegan xoups. 

It’s not too late, X. Exit, detox, self-examine and come back a reformed character.