I feel sorry for anyone that would actually think of Howard Stern as a guilty pleasure

I've only ever caught snippets of his old radio show (there was a time when it was re-broadcast as a television program on late night cable on a local station) and I'll admit that it was generally appalling bad in terms of low-brow gutter talk radio. However when Howard actually turns his attention to a worthwhile discussion, he can be an astonishingly articulate and interesting person. He comes across best in conversation with David Letterman, where the verbal sparring is fantastic. Sadly the opportiunity to see that side of him only happens a couple of times a year. As a broadcaster, I feel he has squandered a considerable talent by sticking to his shock jock shtick for some 30 years.

Ugh, I'm not sure why people even listen to this crap

Unfortunately I haven't listened to him once since he went to Satellite.  He hasn't turned out to be the savior Sirius and its investors thought he would be and rumors have been flying that Sirius will be bought out by XM and Stern may go back to radio.  People have always had strong opinions of him one way or another, and he's never afraid to voice his opinion, making him great for radio and conversation.

The bottom of the entertainment barrel as far as I'm concerned. 

Sick pervert that filled with filth!

Kind of liked him at one time until he one day made jokes about the Columbine massacre. I really haven't cared for him since.

he speaks his mind without giving a damn what others think, its the way it should be and is what makes him so awesome.

I have watched and listened to him on occasion, but overall I could not care less, one way or the other.