20 years of provocation: The best and worst of Howard Stern

To self-identify as ‘The King of All Media’, you need a fundamental understanding of how media operates, enough to know how it shifts over time. Howard Stern has operated as a brute force for over four decades, but a shift occurred in 2006 when he moved to SiriusXM, taking his shock jock oeuvre into a new era.

Satellite radio was a failing medium at the time. A crumbling empire, either calling for a replacement or a stern voice that would rejuvenate it like the red-hot sting of an iron rod. A shock jock pioneer who knew which buttons to press to make his guests antsy yet open, someone whose game wasn’t just being provocative for the sake of it but which cut through the bullshit in a way no one else did, or would again.

In the years prior, Stern was a name already associated with such a demeanour, a menace who didn’t just operate under the rage-bait tail-end of rock ‘n’ roll journalism but pushed with purpose, a mind that came equipped with all the right knowledge, enough to know where the weak spots lie. Enough to know when guests would crack and audiences would listen closer, a storm for the kind of listening that made people eager to know what was coming next.

But it wasn’t always about being savage; it was also about being revolutionary by pushing boundaries, coasting the line between what was considered respectable, expected even, and what people thought was a modern-day approach to journalism that wasn’t afraid of its own tendency to bite, guide, and reshape any situation it found itself in. And when it came to the downfall of satellite radio, Stern’s SiriusXM stint paid off in spades, for both himself and the medium. And sometimes, his guests.

But he also embraced a more internal shift with this transition, one that took the earlier mayhem-induced environments of his earlier endeavours and painted it with more maturity, a different approach to getting under the skin of his guests that blended the two worlds together, maintaining the core hues of his earlier mannerisms with something more modern, something more accessible for new audiences, who could enjoy the cut and dry nature of his approach and also get something out of it – learn something new about the person on the show, or the music industry as a whole.

But with this comes another emerging trend, especially with the possibility of his SiriusXM reign coming to an end: Is culture calling for something new? Or is the final curtain call long overdue? As we dig deeper, let’s take a look at some of the best and worst of Stern over the years…

The best: the changing radio landscape

There’s a reason Stern has a reputation as one of the best interviewers of all time. And if you look past many of his controversial moments, it’s easy to see why. For instance, it’s hard to think of anybody who’s gotten their guests to open up as much as he has, especially if you look back on some of the more obvious examples, like Paul McCartney, Bruce Springsteen, Neil Young, and even political figures like Joe Biden.

During his interview with Young, Stern provided the space for Young to discuss other facets of CSNY that music lovers likely hadn’t even thought of before, like how they learned the hard way not to get too caught up in the weeds of perfectionism, how this revealed different skills along the way, and what can happen when you try to do nothing other than be “too good”.

Howard Stern - Broadcaster - 2020
Credit: Far Out / YouTube Still

But Stern is almost always dealing with the high emotional complexities of any situation, and his years in the game makes him one of the more experienced players when it comes to pivoting a conversation at the drop of a hat, and knowing when to poke and prod, and when to apply a more serious tone to get to the heart of the matter. Obviously, this often coasts a thin line between what many consider to be disrespectful, but when it works, it works.

Perhaps the most telling facet of Stern’s impact is that his own favourite interview was with Conan O’Brien, one of his more sincere encounters that proved his capabilities not just as a provocative shock jock but someone who knows the importance of being genuine in the most naturally conversational manner possible. As he reflected afterwards, “I went home after the interview, and I said, ‘For the first time in my life, I feel like I asked everything I wanted to ask.”

The worst: crossing the line

But of course, these observations often do too little to distract from the fact that Stern’s approach hasn’t always worked out for the better, and often leaves a bitter taste in the mouth of whoever’s watching or listening to the fact that sometimes, Stern does go way too far. Younger audiences might remember when one older clip recently resurfaced, one from Stern’s 2001 interview with actor Natasha Lyonne, when he pushed a little too hard about her parents (“Is it true that you’re the best girl to date because you’re always looking for your daddy?”).

And while some of these have become more subdued over the years, there are still moments when that familiar Stern line of questioning peers through the veil and prickles your skin. Like in 2020, when asking Harry Styles about his therapist, Stern insinuated that Styles was probably sleeping with her. He also told the singer, “You’ve got some father issues. You need a strong male figure in your life. You need a male therapist.” He’s also fat-shamed both Gabourey Sidibe and Sam Smith, and once crafted a particularly distasteful Dolly Parton soundbite that didn’t go down well with the singer.

The list goes on. Which brings up other questions about Stern’s place in contemporary culture, and whether these moments point towards a bigger issue of modern relevance. Obviously, not all of Stern’s interviews are packed with such abhorrent examples of Stern-gone-too-far, with most of them now veering more into thoughtful and more considered territory. But even though many of those quintessential Stern characteristics remain, is it enough in the age of multimedia broadcasting?

Is this the end of ‘The King of All Media’? Or is it merely another shift proving Stern’s long-suspected ability to pivot at the eleventh hour?

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