OK, I've tried giving all of my items to the loner. After he wound up with the mop on his head, I realized that the seeming appearance of long, dirty hair sounds like the description the art student gave of an artist. So I figured if I gave him more stuff, he would be transformed one step at a time into the perfect artist. I'm really surprised I couldn't give him the chalk or blue paint, since those could be art supplies. I tried talking to him about the "search for an artist" but that did nothing either.

What crucial step am I missing?

My inventory now is Batteries, blue paint, chalk, chain, coffee filter, chart, bottle, cheese, glasses, glue stick (the game allowed me to rub glue on the loner's face without subtracting it from my inventory), grass, mirror, perma-tie, scalpel, soldering iron, and syringe.

This game is tough...