My best interpretation as to the point of this image, and/or this submission, is to test whether any pg-created content will automatically rise to the top of Hacker News regardless of its actual merits.

It was probably posted because it's inexplicably random for pg.

is this a not-so-sly reference to Vonnegut?

http://vonnegutsasshole.blogspot.com/2007/04/authors-and-the...

Does this image have an Origin story?

It seems far too Random to exist on it's own.. I had thought it might be related to Asterisk, the Open Source PBX software, but the name on the file says 1995..

"Your search - link:www.paulgraham.com/asterisk.html - did not match any documents."

"Feel free to use this image however you like. It would be nice if you mentioned it was drawn by me, but you don't have to if that would be graphically inconvenient."

I have to admit that it would be amusing to use that quote as permission to launch a new website, using *Man as it's logo.. The perpetrator could launch with its new site with cleverly adjusted fonts-

New Loobot, (with logo by) PAUL GRAHAM!

As far as I remember it appeared on the front page of Paul Graham's site around the time "What you can't say" was first published.

I thought of the free software based Asterisk PBX too. Maybe a modern interpretation is that the face represents someone making a poor comment as they disagree with someone, basically spewing dial tone!

:-*

According to Wikipedia, he's kissing: http://en.wikipedia.org/wiki/Emoticon#Common_examples

Maybe this image is for a default user avatar when none exists already?

I want to draw something random and have it make it to page one.

('*')

probably when he listened to one too many pitches (that he didn't ask for)

pg writes nice essays. what was my point? oh yes, pg writes nice essays :)