This week, there have been many celebrations of the 30th anniversary of the emoticon, the now-ubiquitous use of punctuation marks to mark emotion in online text. On September 19, 1982, at 11:44 a.m., Scott Fahlman posted a message to a Carnegie Mellon bulletin board, proposing that :-) be used for marking jokes and :-( for non-jokes. Though Fahlman should get full credit for these pioneering smiley and frowny faces, there were in fact much earlier pioneers in expressive typography.

Forty-five years ago, in 1967, Reader's Digest suggested that people were already using emoticon-like glyphs in personal correspondence. Barbara Mikkelson provides the passage on the Snopes website:

Many people write letters with strong expression in them, but my Aunt Ev is the only person I know who can write a facial expression. 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 —) Will Wamsley is the new superintendent over at the factory. Marge Pinkleman says they tried to get her husband to take the job —) but he told them he couldn't accept less that $12,000 a year —)
(Reader's Digest, May 1967, p. 160, citing Ralph Reppert of Baltimore's Sunday Sun)

Aunt Ev's tongue-in-cheek symbol seems distantly related to Fahlman's joke marker, as does a suggestion made by Vladimir Nabokov when interviewed by The New York Times two years later:

Q: How do you rank yourself among writers (living) and of the immediate past?
Nabokov: 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.

Nabokov's "supine round bracket" is smiley indeed. But we could just as easily be celebrating the 125th anniversary of the smiley emoticon, because on September 25, 1887, Ambrose Bierce made a similar suggestion in the pages of the San Francisco Examiner. Bierce, who found literary fame as the author of such satirical works as The Devil's Dictionary, had just begun writing his column "Prattle" for The Examiner, under the new management of William Randolph Hearst. (Hearst had been given control of the paper at the tender age of 23, after his father George had purchased it.) In Bierce's column, he proposed introducing "an improvement in punctuation — the snigger point, or note of cachinnation," which would be "appended with the full stop to every jocular or ironical sentence." (Cacchination means "loud, convulsive laughter.") In the newspaper, it was represented by a right parenthesis lying on its side, imitative of a smile, like so:

The section of Bierce's column on the "snigger point" was reprinted far and wide in October and November 1887: by looking in digitized newspaper databases I've found it appearing in such papers as The Chicago Tribune, The Sioux County Herald (Iowa), The Kansas City Times, and The Daily Morning Astorian (Oregon). The following February, in The Traveler's Record (published by the Travelers Insurance Company), Bierce's proposal was warmly embraced.

These other periodicals simply credited The Examiner for the insight, since Bierce was not yet a famous writer; later, in 1912, the complete column appeared (with some revisions) in The Complete Works of Ambrose Bierce, not long before the writer's mysterious disappearance in Mexico.

But even earlier than Bierce, an item in the March 30, 1881 issue of the American humor magazine Puck entitled "Typographical Art" arrayed punctuation marks to create facial expressions of "joy," "melancholy," "indifference," and "astonishment."

Was the anonymous wag in Puck the very first to turn typesetting marks into emotional glyphs? Perhaps so, but further excavations could turn up even more ancient proto-emoticons. The task of making text seem more like our face-to-face interactions has clearly posed a long-standing challenge, and many creative minds have come up with their own independent inventions.