I used to listen to Stern in the early and mid-90s. His bits were mostly juvenile and mostly unfunny, but his on-air tantrums against his staff and against network executives were often hilarious. He's also one of the best interviewers I've heard - he can get people to open up and reveal things they'd never say to other interviewers.
But that was a long time ago. Stern hasn't been interesting or entertaining in years, certainly not since he moved to satellite radio.
Last notable thing I heard from Stern was his live coverage during 9-11.
While every other channel was being politically correct and not wanting to guess at anything, Stern was being real.
I remember him saying “You know that second building is coming down”.
However over all I end up feeling Stern is a nasty opportunist and phoney.