Howard Stern has a job that many of us would take for grocery money – chatting in his plush studio with some of the most fascinating figures in the world. But you or I don't have the audience that Stern's built for himself over the years, one that Sirius XM satellite radio famously pays through the nose to get.
Stern is the highest-paid entertainer in radio thanks to his Sirius XM contract, which he re-upped back in December of 2015 for a five-year extension and a $10 million bump in annual salary, bringing him to an impressive $90 million a year. This is just speculation, but with his current five-year extension almost up, it's possible that if Stern is able to negotiate another comparable raise to stay on at Sirius XM for another five years, he could soon be making $100 million a year for his radio talk show.
Stern is also enjoying a career renaissance in the publishing world. May 2019 saw the publication of Howard Stern Comes Again, a collection of transcripts of his best interviews, or as he prefers to characterize them, conversations, with guests on his talk show (including famous names like Madonna, Jerry Seinfeld, Mike Tyson, Billy Joel, Lady Gaga, and more), along with new commentary by Stern. It hasn't been reported how much Stern made to write the book, his third, but it is known that Simon & Schuster (which published Stern's earlier book Private Parts) was very enthusiastic to get back into the Stern business, so it figures that they probably shelled out a generous advance and additional compensation to Stern for his work on the book.
He may be at least a hit TV show and movie (and possibly a hit single or two) away from literally being King of All Media, but Howard Stern is nevertheless making plenty of money on an annual basis.