Boing Boing pointed me to this article (at the soon-to-be-defunct Gray Lady):
A historical newspaper specialist at the digital archival company Proquest believes he has found an example of a sideways winking smiley face embedded in The New York Times transcript of an 1862 speech given by President Lincoln. . .
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In the transcription of President Lincoln’s speech, which added comments about applause and shouts from the audience was this line:
“… there is no precedent for your being here yourselves, (applause and laughter ;) and I offer, in justification of myself and you, that I have found nothing in the Constitution against.”
Bryan Benilous, who works with historical newspapers at Proquest, said the team felt the “;)” after the word “laughter” was an emoticon, more than a century before emoticons became a widespread concept.