Stern was a strong interviewer 90s-2000s when he'd get something unique out of big name celebrities. You wouldn't hear A-listers talk like that anywhere else back then. Now you have Twitter where they tell you how big the last shit they took was.
Some celebs would try to get in on the act, and be assholes. That or he would set them up to get trolled and fuck with them. He was like a media terrorist, one of the most negative, bitter, jealous, petty little kikes to ever make himself known - and I loved him for it. He was shameless in everything he did. As previously stated, he commanded respect and threw his weight around with malice. He would out big name producers, roast media executives nobody knew by name, he really pulled the curtain back on entertainment. He changed everything.
He was never particularly talented, not really funny on his feet, but he understood the genre. You pick a stance and stick with it. As a jew, he was a natural argumentative, disgruntled prick. It worked for him. The guy was a brand in itself, if he slapped his name on it you knew what you were getting.
The touchy feely chick flick movie put a dent in his reputation. Son of the Beach may have been eye rolling, but it made me laugh a few times. I appreciated the spirit of Stern's work, as a NYC kid myself it was a cornerstone of my humor growing up. To see what he has become would be more painful if I didn't completely understand it from a business POV.
I contend that his show was still listenable until the final Artie years, where I actually began to despise Artie for his annoying unfunny interruptions. I now know he was high out of his mind. I was just a kid at the time, I didn't know what a heroin addict sounded like.