Adobe’s Aseem Agrawala (whom you have to thank for tons of great Photoshop features like auto-alignment/blending of layers) & Aaron Hertzmann have been working with university researchers to apply crowdsourcing data to the problem of font selection:
Have you ever been overwhelmed by the huge menu of possibilities when choosing a font? A simple menu of fonts made sense when there were 20 fonts on our computers, but now we have hundreds and even thousands. Online font repositories have over 100,000 fonts. Our interfaces our based on the idea that fonts can be described with attributes, like “friendly” or “legible;” We use crowd-sourcing and machine learning to compute attributes for any font.