Here’s what’s reputed to be an archive of the first e-mail message that included a smiley. —The First Smiley (Microsoft)
[I wish I’d found it instead of Micro$oft. :( In 1979, someone named Kevin MacKenzie suggested the symbol -) for “tongue in cheek”. It’s not a “smiley”, of course, but it serves the same function. I’ve archived MacKenzie’s post here.