Howard Stern Talks Trump, Mortality and His New Book

Radio’s reigning king of controversy is getting introspective.

Now 65, the master interviewer is reflecting on his notorious career, showcasing his evolution throughout decades of fame in the new book, Howard Stern Comes Again — his first in over 20 years. Ahead of the new release, Stern opened up to New York Times Magazine about everything from Donald Trump to the terror of mortality.

The legendary host discussed his shift from the bawdy, antagonist celebrity interviews that made him famous to the more refined, biographically-driven conversations that have come to define his more recent work. “I had always wanted to do interviews that had substance,” Stern told NYT Magazine’s David Marchese. “The problem was that, in the old format, you couldn’t.”

The self-proclaimed “poster boy for doing everything offensive” didn’t shy away from addressing past wrongs from the wilder days of his controversial career, including his infamous grilling of an audibly uncomfortable Gilda Radner in 1983, as well as his “brutal” commentary on Rosie O’Donnell, for which he claimed to have apologized. “At some point I realized how much I admired her,” Stern said of the comedian. “She’s a fabulous comic, she’s brilliant, and I began to develop a relationship with her.”

Stern also spoke about his relationship with Donald Trump, a long-time acquaintance and frequent guest in the earlier days of Stern’s career, before the presidency made the previously fame-thirsty real estate developer “one of the worst radio guests.”

“Donald is a well-guarded personality,” Stern said of the president. “I think he’s actually so emotional that somewhere along the line he had to close it off.” The host went on to share his belief that Trump’s presidency was merely a publicity stunt. “Deep down he did not want to be President,” said Stern.

The notoriously loud-mouthed antagonist also showed his vulnerable side, discussing a 2017 health scare about which he had previously been uncharacteristically tight-lipped.

“This was my first major health sock-in-the-head,” Stern said of the probably cancerous cyst he had removed two years ago. “I couldn’t bear telling the audience that I was human …. I could not bring myself to admit my own mortality.”

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