Howard Stern is amazingly (and surprisingly) successful. People who criticize him a) haven't really listened to him b) are jealous of him c) both. He is actually very humble, very private and very shy.
PLEASE! Howard was funny about 20 years ago when all the stuff was new and fresh. He has been doing the same old stuff since then and quite frankly I find him to be repetitious and boring. And that hole Robin ... SHUT UP! The end for me was when his PR caught up with him and he ended up divorcing his wife. He had been preaching that he was true blue and loved his wife even makig a 2 hour movie about it ... hypocrite!
There are so many more talented personalities out there that he is being left by the side of the road. The biggest thing that killed him was losing the talent of Jackie Martling! The one that made him the king!