Stern and Mr. Trump are New Yorkers, similar in age, and accomplishment in their field since the early 1980’s.
NYC is all about titillation.
Tri-state listeners have been weened on that kind of humor and don’t find it as offensive like flyover country - bible belt folks might.
I don't find anything funny about Stern. Rather he's a symptom of the degeneracy of America. So it's better for an intelligent person not to associate with him.