I want you to picture the media landscape of
the early 1990s for a second. Okay. It is so
clean, so corporate. You know, you have these
network news anchors who look like they were
just manufactured in a factory somewhere. Perfect
hair, perfect diction, not a word out of place.
Exactly. And then on the radio, you have all
these DJs who use that same, like, deep, fake,
baritone voice. Time for the morning zoo. It
was just... It was safe. It was sterilized. Oh,
it's incredibly sterilized. I mean, you had the
gatekeepers, the SEC, the networks, the big book
publishers, and they were controlling absolutely
everything that reached the American public.
There was a very, very narrow lane of what was
considered acceptable entertainment. And then
into all of that, you have this one guy, a guy
who looks kind of like a heavy metal guitarist,
speaks like an erotic patient on a therapy couch,
and is openly at war with his own bosses. on
the air. And somehow this guy looks at that entire
sanitized system and just says, I'm going to
conquer all of it. And he didn't just say it.
I mean, he statistically did it. And that's really
what we are unpacking today. We aren't just talking
about a shock jock. That term is actually kind
of reductive. When you look at the data, we're
looking at the numbers behind the title, the
king of all media. Because, and this is all in
the source material, there was a specific moment
in time where Howard Stern had the number one
movie, the number one book, and the number one
soundtrack in the country. All at the same time.
Simultaneously. Which is just, it's unheard of.
I mean, even if you look at modern stars like
a Taylor Swift or The Rock, they don't usually
hold the number one spot in film, publishing,
and music at the exact same second. Precisely.
It was a statistical anomaly. So our mission
for this deep dive is to figure out how he did
it. We're going to tear apart the biographical
data to understand the psychology. We'll look
at the court records from his, you know, his
long war with the FCC. And we are going to get
technical on the financial structures of that
half billion dollar serious deal. We want to
understand how a painfully introverted kid from
Long Island weaponized his own insecurities to
build a business empire. And when you say introverted,
I think a lot of people might roll their eyes
at that. Oh, for sure. Because the character
of Howard Stern, the persona. Feels so large,
so loud, so confident. You'd assume he was the
class clown. The guy standing on the table in
the cafeteria just screaming for attention. And
that is the first paradox we encounter. And honestly,
it's probably the most important one. If you
skip this part, you miss the whole story. Right.
If you go back to his early life, he was born
in 1954 in Queens. They moved to Roosevelt and
then Rockville Center. He just he wasn't the
loud mouth. When he transferred to Southside
High School at age 15, the records, the anecdotes,
they all describe him as a total introvert. A
total introvert, like didn't talk to anyone kind
of introvert. Completely. In fact, if you look
at his yearbook, it lists only one student activity
membership in the Key Club. That's it. That's
it. He wasn't the star of the school play. He
wasn't the quarterback. He was the kid in the
corner. His sister was also noted as being very,
very quiet. It was, by all accounts, a quiet
household. So where does the desire to be heard
come from? I mean, if you're that shy, usually
you run away from the microphone. You don't make
it your life's work. Well, it seems to stem from
a very complex dynamic with his father, Ben Stern.
Okay. Ben was a radio engineer. He worked at
a station called WHO in Manhattan, and he co
-owned a recording studio called Aura Recording
Inc. Now, Howard, as a kid, observed something
very specific about his father. He's been on
record saying he always felt his dad was critical
of him, that his dad thought he was a dummy.
Oh, that's rough. It is. But Howard noticed a
loophole. A loophole for affection. Or for respect.
Exactly. For respect. He noticed that his father
treated the people he worked with, you know,
the on -air talent, with this immense reference.
Howard would visit the studio and he'd watch
these voice legends like Don Adams. The guy who
played Maxwell Smart and Get Smart. That's the
one. He'd watch them recording lines and he saw
his dad's face just light up. He treated them
like gods. So Howard thought, okay, maybe he
could look at me with that kind of respect if
I could get behind a microphone. That is heavy.
So the logic for him becomes, if I want dad to
love me or at least respect me, I have to become
a disembodied voice. I have to be the guy in
the headphones. Bingo. It's a classic psychological
transfer. He equated being on a microphone with
being worthy of respect. And that's where the
basement tapes come in. Yes. And this isn't just
a kid playing pretend radio. He's down there
in the dark in his dad's basement in Long Island.
And he's building a simulation of a world where
he is powerful. And the content of those tapes
is surprising. You'd expect a kid in the 60s
or early 70s to be, I don't know, mimicking the
news or introducing Beatles records. Right. But
he wasn't. doing that at all. He was doing the
Howard Stern show before it even existed. He
was doing a character called the Psychedelic
Bee. He was doing prank calls. And here is the
real kicker. Even then as a kid, he was doing
explicit shows. Explicit? How so? He was using
marionettes to entertain his friends with these,
uh, let's just say R -rated skits. With puppets.
He was doing R -rated stuff with puppets. Or
maybe even X -rated. And this is the critical
insight here. The whole shock jock thing wasn't
a marketing strategy he invented in his 30s to
sell ads. It was his native language. It was
his default setting. It was the only way he knew
how to break through that feeling of invisibility
he felt at school. He had to be so loud, so abrasive
and so shocking that you simply couldn't ignore
him. The DNA of the entire show was being formed
right there in that basement. It's amazing that
the content was explicit even then. It's like
the impulse to shock was just hardwired into
him from the beginning. It seems so. But he didn't
go straight from the basement to stardom. The
early career pass sounds. Well, it sounds like
a disaster, frankly. Disaster is a very fair
word. It was a grind. He went to Boston University
for communications. He worked at the campus station,
WTBU. He actually co -hosted a show there called
The King Schmaltz Bagel Hour. The King Schmaltz
Bagel Hour. That's a great name. And it was canceled
after its very first broadcast. Why? Because
they did a sketch called Godzilla Goes to Harlem.
Oh, no. Yeah. It was racially insensitive, obviously,
and the university administration shut it down
immediately. So the pattern of push boundaries,
get punished started literally on day one of
his broadcasting career. Canceled after one show.
That is some serious foreshadowing. But he graduates
in 1976. Does he get a job in radio right away?
No, and this is a funny little detour in his
story. He actually took a marketing role at a
big advertising agency, Benton and Bowles. He
was trying to be a straight corporate guy. Right,
fit into the system. But he hated the department
he was in. So he quit without giving notice to
take a job in their creative department. Same
company, just a different floor. That is a bold
move. A little too bold. The creative department
realized he was the same guy who had just quit
the other department without notice, so they
fired him after only three hours. Fired after
three hours. That has to be some kind of corporate
record. It definitely shows a certain lack of
conformity. He just didn't understand why the
rules applied to him. But he eventually landed
a real radio gig at WRNW in Briarcliff Manor,
New York. OK. And this is where we really need
to talk about his commitment level, because I
think people see the limousines and the Hamptons
house today and they just assume it was easy.
Right. The pay at WR &W was ninety six dollars
a week. Ninety six dollars. Oh. A week. Even
in the late 70s. You can't live on that in the
New York area. No, you absolutely can't. He was
desperate to save money. So to make ends meet
while he was working these insane split shifts,
he was the production director. He did on air
shifts. He did public affairs. He was doing everything.
Everything. Everything. To save money, he rented
a room in a monastery. Wait, hold on. Howard
Stern, the guy who would later make a career
out of strippers and burping contests, lived
in a monastery. In Armonk, New York, he was renting
a room from the monks. I mean, can you imagine
the contrast? spending his days trying to be
this wild, crazy radio guy, and then his nights
are in this silent, holy place just to save a
few dollars. That paints a very different picture
of his work ethic. It does. This was a guy willing
to endure total isolation and poverty just to
stay on the air. That is some serious dedication.
So he's at WR &W, then he moves to WCCC in Hartford,
Connecticut. And this is where the team starts
to come together, right? Yes. Hartford is pivotal
because that's where he meets Fred Norris. Fred
was the overnight disc jockey. And anyone who
listens to Stern knows that Fred Norris became
the longest serving member of the team, the sound
effects genius, the writer. They met there in
1979. Okay, so Fred's on board. But the real
stylistic shift... The birth of the persona as
we know it happened in Detroit at a station called
WWW. WWW 4Ws. And that's where he decided to
drop the DJ voice. Exactly. I mean, up to that
point, he had been trying to be a traditional
DJ. He was trying to do the deep voice, the whole
coming up next Led Zeppelin shtick. But the ratings
weren't great. The station was struggling. So
one morning out of what seems like frustration
or maybe just exhaustion, he made a conscious
decision. He said he wanted to cut down the barriers,
strip down all the ego, and be totally honest.
What does that even mean in practice on the radio?
It means if the coffee machine broke, he talked
about it for 20 minutes. If he had a fight with
his wife that morning, she talked about it. He
realized that just talking... Being raw, being
himself, was way more compelling than introducing
records. He stopped serving the music and started
serving the personality. So it's the moment the
act became reality. That's a great way to put
it. But Detroit didn't last. The station flipped
formats to country, which he didn't love. He
hated it. He called his on -air name Hop Along
Howie. It was a disaster. Hop along, Howie. Right.
He couldn't see himself as a country DJ. So he
moved to Washington, D .C., to a station called
WWDC. And this is the final piece of the puzzle
regarding the core team. This is where he was
paired with a newscaster named Robin Quivers.
And the story of the meeting is interesting because
she hadn't even met him when she took the job,
had she? She hadn't. She was a former Air Force
nurse and a reporter in Baltimore. The station
sent her a tape of Stern interviewing a prostitute
on the air. That was her official introduction
to him. Most people would hear that and run for
the hills. She listened to it and accepted the
job. She thought she would just come in, do the
news, and leave. But as she later said, it wasn't
that way. They had instant chemistry. She became
his anchor in more ways than one. Literally and
figuratively. She was the laugh track, she was
his conscience, and she was the audience surrogate
all rolled into one. So the team is finally set.
Howard, Robin, Fred. He's killing it in D .C.
The ratings are tripling. And then the mothership
calls. NBC, WNBC in New York. This was supposed
to be the dream job. It was the dream. I mean,
returning to New York, the number one market,
working for the National Broadcasting Company.
But as Stern later put it, it was welcome to
my worst nightmare. And this is where the story
really shifts from guy trying to make it to guy
at war with the system. I mean if he was getting
the ratings, why did NBC hate him so much? It
was a culture clash. A massive, massive culture
clash. NBC was a conservative corporate environment.
They had just seen a critical news report on
this new phenomenon of shock radio that featured
Stern. And the executives were already nervous
before he even started. So they were on edge
from day one. They actually debated canceling
his contract before he even broadcast a single
show. Instead of firing him, they decided they
were going to control him. Control Howard Stern,
good luck with that plan. It went about as well
as you'd expect. They gave him this long list
of restrictions. No sexual discussions, no religious
discussions. In his first month, he got suspended
for a sketch called Virgin Mary Kong. Virgin
Mary Kong. Yeah, it was a video game sketch that
involved men chasing the Virgin Mary around a
singles bar in Jerusalem. Okay, yeah, I can see
1982 NBC executives sweating through their suits
over that one. It got so bad that the station
hired a lawyer specifically to listen to the
show and operate a seven -second delay button.
You're joking. not. Think about that expense.
They paid a lawyer a full time salary just to
sit there in a booth and censor their own morning
guy. They also installed a program director named
Kevin Matheny, whose sole job, it seems, was
to enforce these rules. And this is the guy Stern
famously nicknamed Pig Virus on the air. Yes.
And this is so important. He didn't just complain
about his boss behind his back. He made the boss
a character on the show. He called him pig virus
to millions of people. He attacked his appearance,
his management style, his stutter. It was brutal,
but it was captivating radio. Because it's the
ultimate workplace fantasy, right? Yeah. Saying
exactly what you think to your boss out loud.
Exactly. And he was also feuding with Don Imus,
the other morning guy at the station. It was
a completely toxic environment. But here is the
thing about Stern the pressure cooker just made
him better. He tripled the ratings at WNBC. He
was gaining market share. But the management
just could not stomach the content. They couldn't
handle it. Not at all. In 1985, right before
he was supposed to go on air, they fired him.
The official term they used was conceptual differences.
Fired while you're delivering the highest ratings
the station had seen in four years. That has
to stink. Oh, absolutely. But this leads directly
to the WXRK era, the K -Rock era. And this is
really where the explosion happens. He refused
to leave New York, right? Didn't NBC offer him
money to just go away? They offered him $50 ,000
to leave town. It was basically, here's a check,
please go be famous somewhere else. Wow. He declined.
He said he wanted to stay in New York and, quote,
kick NBC's ass. And he did. He signed with Infinity
Broadcasting, moved to WXRK, and within a year,
he was syndicated. This is the official start
of the king of all media reign. So let's talk
numbers here for a second, because the scale
of his popularity in the 90s is just... It's
hard to grasp today with how fragmented media
is. It is really difficult to compare. I mean,
today, a big podcast might have a few million
downloads a month. At his peak at WXRK, Howard
had 20 million daily listeners, 20 million people
tuning in every single day. His show was syndicated
in 60 markets across North America. He wasn't
just a New York phenomenon anymore. He was a
national event every single morning. If you drove
through any major city in the U .S. during the
morning commute, chances are half the cars were
listening to him. And he started branching out
into other media. really testing the waters of
his popularity. The pay -per -view specials were
a huge part of this. These were massive moneymakers
and, more importantly, a proof of concept. In
1988, he did a special called Howard Stern's
Negligee and Underpants Party. It grossed $1
.2 million, but the really big one was on New
Year's Eve 1993. It was called the Miss Howard
Stern New Year's Eve pageant. The one with the
mock beauty pageant. That's the one. It grossed
$16 million. An estimated 400 ,000 households
bought it. It broke the subscriber record for
a non -sports pay -per -view event. And the reviews
were not great. The New York Post called it the
most disgusting two hours in the history of television.
But it proved that his audience would pay directly
for his content. This was the first real sign
that a subscription model could work for him
decades before he did it and then came the books
Private Parts. Private Parts was a cultural juggernaut.
It was released in 1993. Simon & Schuster, the
publisher, did an initial print run of 225 ,000
copies, and they sold out in hours. Hours. Hours.
In five days, it became the fastest -selling
title in the publisher's history. It spent 20
weeks on the New York Times bestseller list.
And what's fascinating about the book is that
it really changed the perception of him. How
so? Because before that, he was just the monster,
right? The shock jock. Exactly. Before the book,
he was just the dangerous guy who made fun of
people. But the book was autobiographical. It
was funny, yes, but it was also incredibly vulnerable.
It told the story of his struggle, his marriage,
his deep insecurities, the miscarriage his wife
suffered. It made him human. It made him human.
Stern himself said, Suddenly, I was a mainstream
performer who had real clout in the marketplace.
I was bankable. And that bankability led to Reckle
to the movie. Which is so rare. Yeah. Radio guys
don't usually become movie stars playing themselves.
It's incredibly rare. But the private parts film,
released in 1997, topped the U .S. box office
its opening weekend. It grossed over $41 million
domestically. And you have to remember, the soundtrack,
which Stern performed on, also hit number one
on the Billboard 200 chart. So that's it. That's
the trifecta. That is the king of all media trifecta
we talked about at the top. Movie, book, soundtrack,
all number one, all at the same time. But with
all this success, He was just getting louder
and more controversial. And, well, we have to
talk about Fart Man. Yes, we do. Fart Man. The
1992 MTV Video Music Awards. It's a defining
image of the 90s, isn't it? Stern, descending
from the ceiling in this superhero costume that
exposed his buttocks, playing a character named
Fart Man. It was pure shock value. It was. But
here's the deep dive nugget. He was actually
developing a Fartman movie with New Line Cinema.
A Fartman movie? Seriously, why didn't that happen?
It fell apart over merchandising rights and content
disputes. Stern wanted total creative control,
and the studio wasn't sure they could sell Fartman
action figures to kids if the movie's content
was super R -rated. Yeah, that's a tough sell.
But it shows you just how much cultural capital
he had at that moment that a major Hollywood
studio was seriously considering a Fartman feature
film. It's absolutely wild, but... While he was
doing the Superhero Act, he was also getting
involved in actual politics and not just talking
about it. He really ran for governor of New York
in 1994. He did. And at first, you know, everyone
thought it was a joke, a publicity stunt. He
ran on the Libertarian Party ticket against the
incumbent Mario Cuomo. But if you look at his
platform, it was surprisingly specific. He had
three main goals, right? Three very clear, very
simple goals. One, reinstate the death penalty.
Two, remove all highway tolls to improve traffic
flow. And three, limit all road work to the graveyard
shift so it wouldn't disrupt commuters. I mean.
He promised that once he passed those three things,
he would resign and hand the governorship over
to his lieutenant. Look, for any commuter in
the New York area, that roadwork platform is
incredibly appealing. It was. He won the Libertarian
nomination by a landslide. People were taking
it seriously. But the campaign ended because
of the Ethics in Government Act. What happened?
To be on the final ballot, he had to publicly
disclose his personal finances. And Stern, being
intensely private about his money, refused. He
said it was none of their business, so he withdrew
from the race. It's none of your business, basically.
Exactly. But here is the amazing... legacy of
that run. George Pataki, the Republican who eventually
won that election, acknowledged Stern's influence.
In 1995, Pataki actually signed a bill limiting
road construction on state roads to night hours.
No way. Yes. It was nicknamed the Howard Stern
Bill. So the guy in the Fartman costume actually
changed public policy in New York State. That
is incredible. Yeah. But his relationship with
authority wasn't usually that constructive. I
have to talk about the FCC. Because this wasn't
just a few complaints here and there. This was
a war. It was a war of attrition. And you have
to understand how the FCC works. They can't find
the talent. They find the station license holder.
The company that owns the station. Right. And
between 1990 and 2004, the FCC levied fines totaling
$2 .5 million against the station owners for
Stern's content. Wow. $2 .5 million. That's a
lot of money, even for a big broadcaster like
Infinity. It is. And the fines were for things
that seem almost tame by today's Internet standards.
You know, talking about sexual practices, bodily
functions. But the FCC saw it as indecency, and
it made Stern a massive liability. Every time
he opened his mic, the station owners were sweating,
wondering if it was going to cost them another
$100 ,000. And this all came to a head after
the Janet Jackson incident. Super Bowl XXVIII.
The wardrobe malfunction. That changed everything.
The Bush administration and the FCC cracked down
hard, I mean hard, on indecency. The walls started
closing in. They were. Clear Channel, a huge
radio conglomerate, dropped his show from several
of their markets permanently. His own management
at Infinity started strictly censoring him again,
just like the old WNBC days. He said he felt
dead creatively. He felt like he couldn't do
his show anymore. And this sets the stage for
the biggest gamble in the history of radio, the
move to Sirius. Let's just stop on 2004 for a
second, because looking back from today, moving
to streaming or satellite seems obvious. Everyone
has Spotify or Apple Music. But we need to contextualize
how insane this move was at the time. It was
widely viewed as career suicide. You have to
remember, in 2004, you bought a radio, you turned
it on, and music and talk came out for free.
The idea that you would pay $12 .95 a month for
radio was laughable to most Wall Street analysts.
And Sirius wasn't a tech giant back then. Not
at all. Sirius was a distressed company burning
through cash and fighting for scraps against
its bigger rival, XM Radio. So Stern is leaving
a terrestrial radio audience of 20 million people,
literally the biggest platform in the world at
the time, for a platform that had What? How many
subscribers did Sirius have? About 600 ,000 subscribers
total. Not for his show, for the entire platform.
He was essentially moving from playing the Super
Bowl to playing a high school gym. So why do
it? Was it just the money? The headline was $500
million, which is obviously a lot of motivation.
The headline number is really misleading, and
that's where the genius of the deal actually
lies. That $500 million wasn't a salary check
for him. It wasn't. No. That was a production
budget for five years. He had to build the studios,
pay the entire staff, pay the writers, pay Robin
and Fred their huge salaries all out of that
bucket. OK, so he's essentially running a small
media corporation himself. Exactly. But the real
wealth, the empire money, was in the stock incentives.
This is the part that business schools should
study. He negotiated these huge tranches of stock
that would vest only if he hit massive subscriber
targets. He was betting on himself. He bet that
he could migrate his audience from free radio
to a paid service. And the analyst said he couldn't
do it. I remember reading quotes saying things
like, loyalty has a limit, and the limit is a
credit card number. They were so wrong. The Howard
effect was immediate and it was massive. In the
first year, Sirius didn't just hit their subscriber
target. They blew way past it. They added millions
of new subscribers solely on the promise of a
show. And on the day of his first broadcast in
2006, the first stock tranche vested. What was
that worth? He and his agent received stock worth
two hundred and eighteen million dollars. Wow.
Just as a bonus. So he essentially equity swamped
his fame. He took his cultural capital and converted
it directly into ownership of the platform itself.
And that's the big takeaway. He realized before
almost anyone else that content was the king,
not the distribution method. If the content is
strong enough, people will buy the new hardware
to get to it. He single -handedly took Sirius
from a niche product for truckers and tech nerds
to a mainstream necessity. But it wasn't a completely
smooth transition. His old bosses at CBS sued
him. They did. It got ugly. They claim he misused
their airtime to promote his new Sirius show
before he left. Stern called it a personal vendetta
by Leslie Moonves, who was the head of CBS at
the time. They eventually settled for Sirius,
paying CBS $2 million, but it just showed how
bitter that breakup was. So he lands at Sirius.
He has two channels, Howard 100 and Howard 101.
He's completely uncensored. He can swear. He
can be as explicit as he wants. But something
interesting happens over the next decade. He...
He evolves. The evolution is the defining theme
of his later career. Once he had total absolute
freedom, he didn't just double down on the shock
value. He actually started to broaden his horizons
in a way nobody expected. And the big public
signal for this was America's Got Talent. Right.
In 2011, he replaces Piers Morgan as a judge
on this huge family -friendly primetime network
show. And he took it so seriously, he actually
forced them to move the entire production of
the show to New York so he could do his radio
show in the morning and then go judge in the
afternoon. And he was good at it. He was. It
introduced him to a demographic that would never
in a million years have listened to the radio
show. You know, grandmothers, kids. And they
saw he was actually a thoughtful, constructive,
and... often kind critic. And we also see him
picking up these serious hobbies. Photography.
He got obsessed with photography. He started
shooting these high fashion layouts for Hamptons
Magazine. He established his own company, Conlon
Road Photography. It wasn't just a celebrity
whim. He studied it. He learned the craft. It
really aligns with that obsessive personality
we saw in the basement with the tapes. He has
to master things. And speaking of personality,
he's been so open about therapy. in recent years
he credits psychotherapy and also transcendental
meditation which he actually started back in
the 70s for saving his life and his sanity he's
spoken at length about how therapy helped him
realize how his narcissism and his constant need
for attention were affecting his relationships
especially his first marriage that the character
was taking over exactly he realized the character
he created was protecting him but it was also
isolating him from everyone he loved and that
introspection led to some public apologies, didn't
it? I know there was a controversy a few years
ago where an old sketch resurfaced. Yes. In 2020,
Donald Trump Jr. tweeted a video of an old sketch
from a 1993 pay -per -view special where Stern
appeared in blackface parodying Ted Danson. It
was, you know, obviously offensive. And instead
of doubling down or making excuses, Stern addressed
it and admitted it. He said, and this is a direct
quote, the shit I did was fucking crazy. Wow.
He credited his years in therapy for helping
him understand why that behavior was wrong and
how much he has changed as a person. It's interesting
you mentioned Trump Jr. because Stern and Donald
Trump go way, way back. Trump was a frequent
guest on the show for years. He was. They were,
in a sense, radio friends. Trump was the perfect
guest for the old show. He was loud, opinionated,
willing to rate women's looks on a scale of 1
to 10. But politically, they diverged significantly.
Right. Stern isn't a Republican. Not at all.
He was a supporter of John Kerry in 2004 and
urged his listeners to oust George W. Bush. And
despite his long history with Trump, Stern became
very critical of Trump's presidency. He even
said in 2020 that he thought Trump despises his
own supporters. It just shows that Stern separates
personal loyalty from his political views. He
also interviewed President Biden recently. in
2024. Which really completes the journey, doesn't
it? From being known as Fartman to doing an in
-depth sit -down interview with the sitting president
in the United States. It is a trajectory that
simply shouldn't be possible. And the style of
that interview was significant. It was. It wasn't
a gotcha political interview. It was a deep dive
into Joe Biden's life, his story of loss, his
psychology. It was Stern doing what Stern does
best now. Empathetic, long -form listening. I
want to touch on the personal side of things
before we wrap up, because you mentioned that
the book The private parts dealt with his marriage
to Alison Burns. They were college sweethearts.
They were. They met at Boston University, married
in 1978 when they were both just 24 years old.
They had three daughters together, but the work
completely consumed him. He's admitted that,
right? Oh, many times. Stern admitted he was
totally neurotic and consumed with work. He prioritized
the show over everything else in his life. They
divorced in 2001. It was reportedly amicable,
but it was clearly the casualty of his ambition.
And he has spoken about that with a lot of regret
over the years. But he found love again with
Beth Ostrowski. Yes, a model and television host.
They married in 2008. And this relationship really
highlights that softer side of him that we talked
about. They are huge animal advocates. They foster
hundreds and hundreds of cats at their homes.
Hundreds. The estimate is approximately 200 cats
a year come through their home. They have dedicated
rooms for it. They nurse them back to health.
And then they find them permanent homes. It's
a far, far cry from the old shock. image. So
the king of all media is on the floor feeding
kittens. If you follow Beth on Instagram you
will see Howard Stern, this media giant, sitting
on the floor feeding tiny little kittens with
a bottle. It's a surreal image. And he's also
dealt with some serious health scares. The king
of all media is mortal it turns out. He had a
very serious scare in 2017. They found a growth
on his kidney. He was convinced it was cancer.
He thought this is it. I'm going to die. Turned
out to be a benign cyst, but it shook him to
his core. It made him confront his own mortality
in a big way. And he's also battled OCD. Yes,
obsessive compulsive disorder since college.
He writes about it in his books, the rituals
he had to perform to alleviate his anxiety, touching
things a certain number of times, counting everything.
It's been a constant struggle for him, and it
explains a lot of his obsessive nature and his
drive for control over his environment. So as
we look back on this entire career, from the
96 stars a week monastery days to the half billion
dollar satellite deal, from the explicit basement
tapes to the White House interview, what is the
big takeaway? What does the Howard Stern story
actually tell us? It tells us that authenticity,
no matter how abrasive or weird it is, is a currency.
Stern didn't just break the rules. He monetized
the breaking of rules. But I think more importantly,
he proved that you can mature without losing
your edge. He successfully pivoted from being
a renegade to being an elder statesman of broadcasting.
Which is a path most shock jocks don't take.
They don't. Most of them just fade away or become
caricatures of themselves. He evolved. It really
is a study in survival and adaptation. Absolutely.
And if we connect this to the bigger picture,
it raises a really fascinating question about
freedom of speech and personal growth. What's
that? Well, Stern spent the first half of his
career fighting the government, his bosses, everyone
for the right to say absolutely anything, no
matter how offensive. He was a First Amendment
absolutist. Right. But now in the second half
of his career. career, he looks back at some
of those very things he fought to say, like the
racial sketches or some of the cruel comments,
and he regrets them. He calls them crazy and
fucking nuts. That is a paradox, isn't it? It
is. And so the question for you, the listener,
is this. Does his career prove that true freedom
of speech includes the freedom to eventually
silence your own past self? Is the ultimate victory
of free speech not just the right to speak your
mind, but the wisdom to evolve and know when
you were wrong? That is something to think about.
Yeah. From the king of all media to the king
of all evolution. Thanks for listening to this
deep dive into Howard Stern. We'll catch you
on the next one.