Chris Rock
Chris Rock caricature by Tielman Cheaney.
So, teeth are one of those aspects of caricature that are hard to get right. Try to clearly delineate every tooth, and you end up with a pretty weird-looking mouth. It just looks like sloppily-made graph paper wedged in there. Don’t put enough detail, and it looks like you forgot to draw something important.
Fortunately, I’m really making fun of his big teeth here. So I just made them big, uneven, and prominent. The lower lip overlapping the microphone was a mistake if I remember correctly, but it works.