Jack Black (2004): As a performer, Jack Black had to grow on me.  It wasn't until I came to CMU and got absorbed into the college counter culture that I truly came to appreciate him.  And when I did, the potential for caricaturing him just blossomed for me.  I think you need to "know" the subject you're caricaturing if you want it to have any hint of accuracy.  If I tried to just caricature him before I knew any of his work, something would have gotten lost in the interpretation.  As it stands, I'm very happy with this drawing.  Drawn in Micron Pigma Marker, Sharpee Marker and colored in Photoshop.