Answer: Scott Fahlman

Although the history of using typography to, unconventionally, display some sort of face goes back over a century, the first person to specifically propose that a set of keyboard strokes be used to stand in for a smile or frown in order to convey an emotional state to the reader was Scott Fahlman—a computer scientist at Carnegie Mellon University.

In a post to the computer science general board at Carnegie Mellon University on September 19, 1982, he wrote the following:

19-Sep-82 11:44 Scott E Fahlman 🙂
From: Scott E Fahlman — Fahlman at Cmu-20c

I propose that the following character sequence for joke markers:

🙂

Read it sideways. Actually, it is probably more economical to mark
things that are NOT jokes, given current trends. For this, use:

🙁

This was not the first instance where a form of typography had been used and/or suggested for use as a way of displaying a facial expression. All the way back in 1881, Puck—a satirical magazine published in the United States—jokingly suggested that multi-line typographical constructions could be used to make faces. However, the idea was never seriously entertained as a method of conveying emotion in print.

In 1912, renowned influential journalist and pioneering writer Ambrose Bierce proposed that writers could append funny or ironic sentences with this typographical construct: \___/ to represent a smiling mouth. Again, this wasn’t a particularly serious proposal and the idea never caught on. Over the intervening decades, the use of characters to construct faces would appear here and there in scattered contexts, but failed to gain any traction.

It wasn’t until Scott Fahlman’s message board post that the general public was really ready for the idea of a typographically constructed face. Computer use was on the rise, more and more people were communicating via email (a rather sterile medium compared to face-to-face and voice-based communication), and a simple way to add an emotional marker, such as a smile, to digital communications was a welcome addition.