I think I like doing caricatures because I'm new to them and I feel like I have permission to do bad drawings. Most of the time, even when I'm just quickly thumbnailing stuff out, I feel guilty if the drawing isn't "good."
Here are two friends of mine. You probably don't know them, so just trust me, they are spot on perfect.
And when I say spot on perfect, I mean they have some issues. I made Joe (the top guy) look quite a bit older than he should, and when Matt saw his caricature, he asked if it was a really mad Barak Obama.
So I drew Obama
I tried to make this drawing more structurally sound than the others, but the problem with doing that is the tendency to make a stiff drawing. I'm also not sold on how I did his forehead.