He was opposite of what he was held out to be.
He was supposed to be a ‘nothing is sacred’ shock jock.
But if you actually listen to his jokes, they have no real target.
He was sometimes obscene, but never actually edgy, since there was no sacred cow that he was taking down. He was vulgar, which dumb people mistook for iconoclasticism, but there were no icons that he was actually attacking, apart from the standard totally safe ones.
And he just wasn’t funny. The jokes didn’t land. Vulgarity can be funny. Lewdness can be funny. But Howard Stern wasn’t funny.
And he was pulling punches. He would be vaguely racist, but never in a meaningful way. Vaguely sexist, but never in a meaningful way.
The whole purpose of the show was for him to give a boost to the sagging careers of minor actors who the studios weren’t quite done with. Stern’s ‘no holds barred’ obnoxiousness was a fig leaf that hid the fact this sole function was to be a professional lickspittle for studio-dregs who needed an emergency transfusion of publicity. Which is why his obnoxiousness never went anywhere—never had a legitimate target, never had a message, never actually rocked any boats.
Howard Stern is not dumb, and his intelligence leaks out in some contexts. But what he is, and all he is, is a corporate radio guy who is following orders and contributing to the corporatization of society.
And the only reason anyone ever liked him is that, back when he was a thing, radio personalities had almost no competition.
But he’s a total failure—not funny, not anything. Made a lot of money—but only by being an obedient corporate fizzle.