Howard Stern loves the sound of his own voice. He was controversial enough that he built up a loyal fan base for a while. However, his buzz has died down considerably, and I don't know of anyone who really is devoted to him anymore. And the people who used to listen to him have pretty much drifted away from him.
Satellite/subscription radio is dwindling, and Stern can't really make it on the open air any more.
Plus, yeah, he has a lot of nerve talking about someone else's looks. He's ugly on the outside, and he's ugly to listen to. I can't stand him myself. I think that he appeals mostly to males in the 16-25 demographic, the ones that like to think that they're dangerous bad boys, but are really all hat and no cattle, as we say here in Texas.