The hedcut algorithm
Super interesting thread on using Mathematica to approximate Wall Street Journal–style hedcut portraits. Okay that probably doesn’t make any sense. Just click through; you’ll understand. It’s fun to watch them work through the problem.

Have you seen StippleGen? Built in Processing, uses a Voronoi algorithm to approximate the dot pattern. It laser-cuts like a dream.
http://www.evilmadscientist.com/2012/stipplegen2/
http://cs.nyu.edu/~ajsecord/stipples.html
An infinitely better stippling algorithm.