The approach is working very nicely, and the tone of the illustration is reading pretty well- It makes me want to read the article. I would say that are far as likenesses go, Jay-Z's head, despite being big figuratively, is a wee bit slimmer up top. The drips coming from the gunshot wounds(?) are looking a little "meh", but that has a lot to do with how they're rendered. It seems like they should either be really stylized or really drippy, but as is, it's teetering between the two.
Great feedback- I do see what your saying about his forehead, I think your the first person to pinpoint exactly whats wrong w/ his face! I also agree about the drips, they do need to be revisited. Will re-post soon once I get more feedback from my internship guy... Thanks Derrick :)