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 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-
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!