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Smile! A History of Emoticons

This summer, Facebook rolled out "stickers" on its website: cartoony takes on the emoticon for users to post in their chats, from a lovestruck cactus to a pizza-eating cat. Still, for many of us, the simple sideways smiley face still reigns in electronic communication.

It started 31 years ago, when a joke about a fake mercury spill at Carnegie Mellon University was posted on a digital message board and mistaken for a genuine safety warning. The board's users cast about for a means to distinguish humorous posts from serious content. On Sept. 19, 1982, faculty member Scott E. Fahlman entered the debate with the following message:

I propose that [sic] the following character sequence for joke markers: :-) Read it sideways. Actually, it is probably more economical to mark things that are NOT jokes, given current trends. For this, use: :-(

The rest is Internet history. Dr. Fahlman's expressive, minimal icons became an integral part of online communication, if not always a welcome one. These "smileys," as they came to be known, were effectively the first online irony marks. But emoticons recur throughout modern history.

Though it is difficult to nail down the first appearance in print, one likely contender appears in an 1862 transcript of a speech by President Abraham Lincoln. The transcript records the audience's response to Lincoln's droll introduction as "(applause and laughter ;)." Without corroborating evidence, however, it is impossible to decide whether this is a true emoticon.

Counting in its favor, the transcript was typeset by hand, before mechanical typesetting brought with it the risk of gummed-up Linotypes accidentally transposing characters. So it is plausible that ";)"—rather than the more grammatically sensible ");"— was intentional. Moreover, later audience reactions to the same speech appear between square brackets rather than parentheses, reinforcing the likelihood that this particular interjection was typeset deliberately.

On the negative side of the ledger, this single ";)" was the only such "emoticon" in the speech, and the rest of the text suffers from enough typographical errors that we cannot be certain it was a calculated addition. Though its form is undeniably familiar, the precise meaning of this first emoticon remains unknown.

The meandering path toward the modern emoticon continued in 1887, when the celebrated (and feared) critic Ambrose Bierce penned a tongue-in-cheek essay on writing reform entitled "For Brevity and Clarity." Alongside helpful contractions of phrases such as "much esteemed by all who knew him" (mestewed), Bierce presented a new mark of punctuation intended to help less fortunate writers convey humor or irony, which he called "the snigger point, or note of cachinnation." (Now almost extinct, "cachinnation" means "loud or immoderate laughter.") It looked like a line with the ends turned up and, he wrote, "represents, as nearly as may be, a smiling mouth." Of course, his proposal was itself an ironic act, and unsurprisingly, the mark didn't catch on.

The last pre-Internet emoticons ambled casually into view at the end of the 1960s. First, in 1967, a Baltimore Sunday Sun columnist named Ralph Reppert was quoted in the May edition of Reader's Digest. Reppert, writing that his "Aunt Ev is the only person I know who can write a facial expression," explained that: "Aunt Ev's expression is a symbol that looks like this: —) It represents her tongue stuck in her cheek. Here's the way she used it in her last letter: 'Your Cousin Vernie is a natural blonde again —)[.]' " Its appearance was apparently a one-off.

Two years later, on a literary plane far removed from the Reader's Digest, another analog smiley sprung from the mind of Vladimir Nabokov. A famously controlling interviewee, Nabokov insisted on being provided with questions in advance. Once, recounting a reporter's question as to where Nabokov ranked himself among writers of his era, the Russian ÊmigrÊ replied obliquely: "I often think there should exist a special typographical sign for a smile—some sort of concave mark, a supine round bracket, which I would now like to trace in reply to your question."

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Smile! A history of emoticons  
Smile! A history of emoticons