This article is part of The Poynter 50, a series reflecting on 50 moments and people that shaped journalism over the past half-century — and continue to influence its future. As Poynter celebrates its 50th anniversary, we examine how the media landscape has evolved and what it means for the next era of news.
In a wide-ranging interview, Howard Stern asked Conan O’Brien about everything from his time as a writer for “Saturday Night Live” to the comedian’s final days as host of “The Tonight Show.”
Stern brushed off the idea that credentials mattered.
“It’s being funny,” Stern said. “And it’s a bitch.”
O’Brien said he’d struggled with self-doubt and had felt depressed. It was an opening for the self-described “King of All Media.”
“Do you suffer from depression?” Stern asked his famous guest outright. “Are you medicated?”
“I’m medicated,” O’Brien confirmed.
“You are?” Stern asked.
“Yeah,” O’Brien said.
“So you go to a psychiatrist and —” Stern began.
“I used to think I needed to be incredibly unhappy to be funny … and people tell you that’s not true,” O’Brien said. “You get to a point where you don’t care if it’s true or not. You really don’t. You just think, ‘You know what? I’d rather be happy.’”
It was a remarkable moment of vulnerability. Stern later called the 2015 interview his best of all time — the kind where the radio host felt like he asked every question he needed to ask.
Long before podcasts turned long-form interviews into the norm, Stern helped set the stage for them — first on broadcast radio, then behind a paywall at SiriusXM. His candid and provocative style morphed, in later years, to a more mature and reflective approach.
With his jet-black curls and face often framed by sunglasses, Stern — who towers over many at six-foot-five — is one of radio’s most recognizable voices. Over four decades, he built a multi-million dollar empire, the foundation of which stemmed from his years as a “shock jock” — a radio personality who attracts listeners by being provocative, offensive and irreverent.
His early interviews could be intense, provocative, and downright demeaning. On “The Howard Stern Show,” he once tried to get Anna Nicole Smith to step on a scale on air. He mocked Latinos’ taste in music, even taking on a fake Mexican accent, after the 1995 murder of Tejano superstar Selena Quintanilla-Pérez. He made disturbing comments about female students fleeing from the Columbine High School shooting.
So great was Stern’s on-air indecency that it earned him a slew of violations and fines from the Federal Communications Commission before he departed from terrestrial radio and joined Sirius Satellite Radio in 2006.
Still, listeners and Stern fans continued to tune in. Love him or hate him, his audience grew.
He once told Piers Morgan his secret to being a longtime entertainer. “I think you have to have a sense of yourself,” Stern said. “I think you have to really understand what people want to hear.”
He traced that instinct back to childhood. His parents would cut him off mid-story if he dragged on. When he made them laugh, he won approval. “This is the way I won love and acceptance from my parents,” he said. “But it was the best training ground in the world. In a sense, I’ve always been doing a radio show.”
Even his nickname — “King of All Media” — was initially a goof. The radio broadcaster said he was always fascinated by Michael Jackson calling himself the “King of Pop.” Stern thought it was obnoxious and pretentious. So he decided to apply it to himself. But with time, the label stuck. And Stern eventually embraced it.
“It’s very difficult to argue sometimes with success,” said Peter Laufer, a University of Oregon professor and an expert in the journalistic interview. Stern’s success is “phenomenal,” Laufer said, “particularly in interviewing. And he knows how to work, not just both sides of the street — all sides of the street.”
But the “shock jock” style burns bridges, Laufer said. John Sawatsky, a longtime journalist, author and educator who has made a lifelong study of interviewing, said it often doesn’t work.
“Most of the time, what happens is it makes them defensive,” Sawatsky said. “And rather than opening up and revealing something about themselves, they close down and become defensive.”
Still, he added, an occasional “trigger word” or “shock word” can produce an unexpected revelation.
Laufer said Stern’s notoriety for quite some time was rooted in his crudeness.
“But it’s hard to argue with that success if I’m just looking at this in the abstract, as an interviewer on the radio. He was and is successful because of that,” Laufer said. He added, “I don’t like the act, but that’s — so what? So what if I don’t like it?”
Stern’s early approach to radio was intentional. He was pursuing what he called a “scorched earth policy.”
“When you’re on the radio and you’re trying to attract an audience, everything is intense,” he told ABC News’ George Stephanopoulos in 2019. “Everything is super blown up.”
During those years, Stern’s focus remained on the clock. He didn’t let his guests get many words in. Ratings drove him, he told “Fresh Air” host Terry Gross.
“When you’re doing an act like mine, you need high ratings. They’re not keeping you around for the joy of it,” Stern said. “They want to be No. 1 because they’re putting up with a lot of government fines, a lot of religious groups complaining, people complaining to get me off the air. So I had to deliver the goods.”
Years of therapy reshaped both Stern and his interviews. He no longer wants fans to read his older books, including his 1993 bestselling memoir, “Private Parts.” He has said he regrets some of his interviews. “That interests me zero, being as dirty as I want to be,” he told Stephanopoulos.
Howard Stern displays his book “Private Parts” at a book-signing appearance in New York on Oct. 14, 1993, which attracted thousands of fans who jammed Fifth Avenue outside the Barnes and Noble bookstore where he appeared. (AP Photo/Ed Bailey)
With time, Stern has embraced a different approach. Recent guests include comedian Nikki Glaser, multihyphenate Jennifer Lopez, and actors Ben Affleck and Matt Damon.
Sawatsky said he’s been told the world-famous broadcaster has shifted dramatically.
“That’s not like the old Howard Stern,” he said, “so he had learned from that.”
“When I’m sitting there, I said, ‘What would it be like to really hear what someone has to say?’ And it has led to some incredible conversation. … I can do what I really want to do. And what I wanted to do is listen to people and ask them questions that I had.”
In December, Stern announced a new three-year contract with SiriusXM, extending a career that has already reshaped the sound of radio and the art of the interview.
“Whatever anybody wants to say about Howard Stern, that mother******* opened the door for all of us,” Joe Rogan once said on his own top-charting podcast. “All of us. For me, 100%.”
Long before podcasting reshaped the media landscape and Rogan, a comedian by trade, became one of the most influential interviewers in the world, Howard Stern had already written, broken and rewritten the rules. He fused raunchy comedy, deeply personal confession and marathon interviews into appointment listening. He proved that audiences would follow a personality, pay for access and spend hours inside a conversation.
Try not to hear Stern when a modern podcast host lobs a crude joke and then pivots to a disarming question. Try not to see his fingerprints on the sprawling, introspective audio interviews that now dominate the media landscape.
Today’s podcasting giants are standing at a mic that Howard Stern held first.
