The City Room blog at the NY Times discusses what looks like a winking emoticon in an 1862 NYT transcript of a speech by Lincoln:

The post goes on at some length. Experts are called in to dissect the space/semicolon/parenthesis - is it a typo, an actual emoticon, or archaic punctuation with a space added to make the line right-justified? There are some interesting reader comments, with the best being:

Ah, if only the Times would go to this length and depth of inquiry when investigating WMD claims.