A dedicated poetry reader appears to have discovered a smiley face in a poem from 1648, a find that would extend the pre-history of the emoticon back by about 200 years.
Editor Levi Stahl, publicity manager for the University of Chicago Press, was taking in some poems by Robert Herrick when he noticed a rather unusual typographic formation in the second line of the poem "To Fortune."
Tumble me down, and I will sit
Upon my ruins, (smiling yet:)
That sure looks like a smiley face.
Now, one can imagine that the printer accidentally included a colon before the close parenthesis. It could just be a mistake. But given the context of smiling yet, it seems more believable that this was an attempt at an orthographic joke. (Perhaps it should even have been a winky smiley face ;).
Why would anyone care about a smiley face in a poem from the 17th century? For me, it's like a wormhole that connects our time with theirs. If you'd been alive in 1648, you might have considered that a colon and a parenthesis form a smiley face. Our ancestors looked upon the same marks on the page and saw the possibilities that we take for granted.
While emoticons have probably been independently invented many times—the earliest documented use of the smiley face with a nose, :-), comes in 1982—Herrick very well could have been the first.
Update: English professor Alan Jacobs files a dissent: "Not that parentheses weren’t used in verse in Herrick’s time — they were — but not as widely as we use them today and not in the same situations," Jacobs writes. "Punctuation in general was unsettled in the seventeenth century — as unsettled as spelling: Shakespeare spelled his own name several different ways — and there were no generally accepted rules. Herrick was unlikely to have consistent punctuational practices himself, and even if he did he couldn't expect either his printers or his readers to share them."