NY Times Word Cloud Portrait?

Question

Looking for a little insight into this app. If you don't know what it is check it out - here's an image it generates:

http://admin.inc.com/2013/03/18/how-to-be-best-in-show-at-sxsw/cloud4975/

I have a customer looking to do the same thing. I could easily fake it - by taking an image with a bunch of words laid out, and then using a hi-con of the face to mask out the words. But that will cut off letters and such... and that's not ideal. So looking for insight into a nesting / fitting algorithm to do this. Anyone know who developed this app for NY Times?

moccamaximum · Answer

This "classic" example could be somehow bended to your needs.

http://help.adobe.com/en_US/as3/dev/WS5b3ccc516d4fbf351e63e3d118a9b90204-7eee.html

I would look into how this algorithm converts shades of grey to ascii-signs.

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