Both a tribute and challenge entry.
I've always wanted to be a successful Jazz Guitarist.
Wip animation here
Edit: Updated taking onek's advice on the shoulder and skin dithering. I've extended the leg a bit, but I won't angle it down, as its incredibly hard to balance a guitar with what appears to be a straight leg :P
Edit 2: Taken Manupix advice, removing a little dithering from the fabric to create a bit more depth/volume. Minor touchups on the face also.
Edit 3: Shaved some width off the right hand to reduce the 'blobbiness' :)