But to answer your question, I have not found a software technique that can generate results as strikingly detailed as the hedcut stipple drawings used in The Wall Street Journal, though some attempts have been made.
If you want a quick and easy effect that won't resemble hedcuts, but might make a good candidate for faxing, try the Graphic Pen or Photocopy filters in Photoshop under the Filter > Sketch menu. You will need to start with a fairly high resolution image to get the best results with these filters.
Another method is to simplify the image as much as possible, then convert to Indexed Color mode using diffusion dithering in Photoshop. This method is explained in an illustrated step-by-step tutorial: How to Make a Photo Suitable for Faxing
For more information on hedcut stipple drawings, see this article from Kevin Sprouls, Creator of the Wall Street Journal Hedcut Portrait, Sprouls Method — the Hedcut, a blog post from Kevin Sprouls, or visit the links under "Wall Street Journal Hedcuts" below.