A fun piece in the NYTimes on the possibility of an emoticon in a 1862 article on a President Lincoln address. Jennifer 8. Lee does a great job sniffing out the possibility, as well as pointing us to the Wikipedia page, which includes examples of them from the late 1800s. The examples below were published in the March 30 1881 issue of Puck. I found the differences between eastern and western emoticon styles to be of particular interest. Western styles ‘read’ horizontal, while eastern ones are vertical. Western smile: : ) Eastern smile: (^_^) Western surprise: :0 Eastern surprise: (0.o)
Of course, the ‘fun/fluff’ aspect of it gives way to the deeper ways that the media shapes the messege. One of the things I found to be particularly pursuasive about the ‘pro-proto-emotion’ arguements was that the reprinting of Lincoln’s speech required typesetting, and the setter had to make the mistake of placing a space before the semicolon as well as the semicolon itself. Two mistakes. 
These things go well with thinking about texting (Times has an older article called ‘Text Generation Gap: U R 2 Old (JK)’) and reading (‘Online, R U Really Reading?’)