Ben Folds
I'm a big fan of the musician Ben Folds! So when I was assigned to create a caricature, I immediately start googling for some photos. He's got a pretty unique look - shaggy hair, thick glasses, turtley neck - that was easy to exaggerate.
This was my first big project with ZBrush, a 3D creation software that feels very much like using clay and paint instead of pushing around vertices. Creating something inorganic, though - like the glasses - can be difficult. Knowing what I know now, I would've instead whipped up the glasses in Maya.
The first step was just creating the caricature, which I quickly did in photoshop. The original is on the left, caricature on the right:
I mostly used the "liquify" and "puppet-transformation" tools. Quick and dirty. The idea was to pick some of the most noticeable features and push them further. The smile, forehead, glasses, and neck all got bigger.
The photo was then brought into ZBrush and sat behind my sculpture as I worked; the early phase of the sculpture was pretty much making my 3D shape match the 2D picture. And this is only a front view: turns out, many musicians don't post perfect side, top, or back views of their head. So I filled in those blanks with some 3-quarters views of Ben Folds from google, and what I know of human anatomy.
ZBrush was very fun to use!