Welcome back to the Deep Dive. I, um, I have
to be honest with you about something right off
the bat. Oh boy. What is it? Well, when I first
opened the file for today, I had a moment of,
uh, of skepticism, I guess you could call it.
Because of the names on the list? Exactly! I
saw these three names stacked on top of each
other. Peter Lawford, Shirley MacLaine, And Tony
Bennett. Right. And my immediate reaction was
just, are we doing a nostalgia trip? Like, are
we just going to sit here and talk about martinis
and tuxedos and old Hollywood gossip? Which is
a very common first reaction, to be fair. It
felt a bit light for what we usually do. Yeah,
you see that Rat Pack label and you immediately
think surface level glamour. You think Las Vegas
in the 60s and snap rim hats and, you know. Ring
-a -ding -ding. Ring -a -ding -ding. Exactly.
But then I started actually digging into the
primary sources you pulled. The military records
and the legal briefs. Yes, specifically those.
And I realized I was completely wrong. This isn't
a story about entertainment at all. No, it really
isn't. It's a story about the 20th century itself.
It's like a masterclass in sociology and business
strategy and frankly, just survival. It really
is. What we're looking at today are three titans
of the industry whose lives intersected in that
incredibly glitzy Rat Pack era, but then diverged
so wildly that it's almost hard to believe they
were ever in the same room. Right. We're looking
at three very distinct case studies on how to
navigate a shifting world. We have Peter Lawford,
the English aristocrat, who basically became
the ultimate insider until the day the locks
were changed. We have Shirley MacLaine, who I
was honestly shocked to learn is basically a
legal scholar and a business shark in addition
to being a mystic. She's a powerhouse. And we
have Tony Bennett, whose life story reads way
more like a gritty war novel than a jazz biography.
And the mission for this deep dive for you listening
today is to find... The pivot points. The pivot
points. Right. We aren't just going to sit here
listing their movies or their hit songs. We are
looking for the very specific moments, a glass
door shattering or a broken ankle or a phone
call to a son that completely altered their fates.
It's really about agency versus circumstance.
So let's unpack this. I want to start with the
figure who I think is probably the most tragic
and in some ways the most complex because of
his passivity. Peter Lawford. The golden boy.
Golden boy. Looking at the photos in the stack
we have, he is the absolute definition of debonair.
But his start in life was chaotic. Chaotic is
putting it very mildly. Really? Oh, yeah. To
understand Peter Lawford, you have to understand
that he was born into a very specific, very rigid
slice of British society, but under incredibly
scandalous circumstances. OK, set the scene for
us. He was born in London in 1923. His father
was Lieutenant General Sir Sidney Turing Barlow
Lawford. OK, so a knight. A decorated military
man. Exactly. Very high status. His mother was
May Somerville Bunny. So far, so aristocratic.
Sounds very proper. But here's the kicker. At
the time of Peter's birth, his mother was married
to one of Sir Sidney's officers. Oh, wow. A man
named Captain Ernest Alen. Ouch. Saw a massive
scandal right out of the gate. Huge. In 1920s
Britain, this was absolute social suicide. May
actually confessed to her husband that the child
wasn't his, which led to a double divorce. A
double divorce in the 1920s. That must have been
front page gossip. It was. Sir Sidney and May
eventually married when Peter was one year old.
But that initial instability really set the tone
for his entire life. Because they were ostracized,
right? Completely. Because of the scandal, they
were largely shut out of their social circles.
So they traveled constantly. Peter was never
formally educated in a traditional school setting.
And his mother sounds like a... a character in
her own right the notes mentioned she had very
specific ideas about his future she was basically
the architect of his reality she explicitly stated
that she decided peter was unfitted for any career
except art unfitted for any career except art
yes she actually cut latin and mathematics out
of his curriculum entirely and substituted them
with dramatics and tennis that is a fascinating
parenting choice just hey You aren't smart enough
for math, so go be famous. It's wild. Right.
It put immense pressure on him to be a personality
rather than an intellectual. But despite this
intense focus on art, there was still this lingering
expectation of military service. Because of his
father. Exactly. Being the son of a lieutenant
general, the military is just the default path
for a young man of his class. It was expected.
Right. But this is where we hit our first major
pivot point, the sliding doors moment of Peter
Lawford's life. He was 14 years old. This is
the glass door incident. It's a moment of pure
random trauma. What exactly happened? He was
running through a room, seemingly just being
a boisterous teenager, and his right arm went
right through a glass pane. The injury was horrific.
We aren't just talking about a few stitches here.
No, not at all. It completely severed the nerves
and tendons. And you have to remember, in the
1930s, microsurgery simply didn't exist. So they
couldn't fix it. No. He essentially lost the
use of his forearm and hand. He suffered irreversible
nerve damage. He eventually learned to conceal
it later in life. He would keep his hand in his
pocket or hold a cigarette to mask the immobility.
But physically, the arm was ruined. And the consequences
of that were immediate, right? Immediate and
severe. A military career was now physically
impossible. Which was the expectations. But the
financial repercussions were somehow even worse.
He had an aunt who had planned to leave him a
considerable fortune, an inheritance that would
have set him up for life. Let me guess. She wasn't
happy. She was horrified. She was so disgusted
that he couldn't serve in the military and that
he was turning to the lowly procession of acting
that she literally wrote him out of her will.
Talk about adding insult to injury, literally.
Yeah. So he loses the inheritance, he loses the
military path, and he is basically forced into
acting to survive. Exactly. And this brings us
to World War II, which is the part of the story
that I find deeply, deeply ironic. Set that up
for us. Well, the war breaks out. Lawford is
in America at this point. His family's funds
are frozen in Britain. He's broke. He's actually
working as a parking attendant and an usher just
to buy food. The son of a knight parking cars.
Right. But Hollywood has a massive problem at
this exact moment. All the men are gone. Correct.
Clark Gable, Jimmy Stewart, Tyrone Power, all
the traditional leading men are deployed. MGM
is absolutely desperate. They need young, handsome
men who look good in uniform to star in these
morale boosting war movies. And here is Peter
Lawford. Yes. Tall, handsome, authentic British
accent. classified 4F because of his arm. He
can't serve. So he gets hired to play the very
thing he physically can't be in real life. Precisely.
MGM signs him and they cast him almost exclusively
as soldiers. He plays pilots, infantrymen, naval
officers. He was in Mrs. Miniver, right? Yes,
Mrs. Miniver, the White Cliffs of Dover, Eagle
Squadron. He becomes this massive heartthrob
playing military heroes while the actual real
heroes are dying overseas. The source material
mentions a modern screen magazine poll in 1946.
Yes, he won it. He was literally voted the most
popular actor in Hollywood. He was receiving
thousands of fan letters a week. He was the golden
boy of the MGM lot. But you have to imagine the
psychological toll of that. It was heavy. He
suffered from severe imposter syndrome. He knew
he was playing a role. He knew his fame was based
on this sort of lie of omission regarding his
service. And looking at his filmography, he wasn't
exactly carrying these movies either, was he?
Like he wasn't doing heavy dramatic lifting.
That's a really key distinction. The critics
were often pretty lukewarm on him. He was charming.
He was debonair. But he was usually just the
best friend or the romantic interest. For a really
strong female lead like Esther Williams or Judy
Garland. He was a personality. Exactly. He was
a personality more than an actor. He was safe.
Which perfectly sets up his next major role in
life, the brother -in -law. He marries Patricia
Kennedy in 1954. This moves him from Hollywood
royalty to actual American royalty. He marries
into the Kennedy clan right as JFK is descending
on the national stage. And this is where Frank
Sinatra enters the picture in a major way. Sinatra?
Sinatra was obsessed with power. He saw Lawford
as a key to that power. He famously nicknamed
him Brother -in -Lawford. That nickname is just
so brutal. It literally defines him entirely
by his relationship to someone else. It's dismissive,
but it was incredibly accurate. Lawford became
the bridge. He was the conduit between the glamour
of the Rat Pack and the political power of the
White House. He organized the fundraisers. He
organized the fundraisers. He brought the massive
stars to the rallies. In 1960, he even became
a U .S. citizen specifically so he could vote
for his brother -in -law. Wow. He was at the
absolute apex of cultural relevance at that moment.
He was starring in Ocean's Eleven. He was skiing
with the president. He was the ultimate insider.
And then comes the fall. And it is steep. We
have to talk about the snub. The snub, yes. This
story is legendary, but let's break down exactly
what happened according to the historical records.
This is the exact moment Peter Lawford's life
effectively crumbled. It's March 1962. Frank
Sinatra is at the peak of his hubris. He feels
untouchable. Untouchable. He expects President
Kennedy to stay at his home in Palm Springs during
a West Coast trip. And Sinatra had prepared for
this, right? This wasn't just, you know, crashing
on the couch. Oh, no. Sinatra had spent an absolute
fortune. He constructed a concrete helipad specifically
for the president's helicopter. He installed
a full presidential communications center with
direct secure lines to Washington. He built guest
pottages for the Secret Service. He viewed this
visit as his coronation as the cultural king
of America. But he had a problem named Robert
F. Kennedy. RFK, the attorney general. RFK was
aggressively pursuing organized crime at the
time. And he knew Sinatra was fraternizing with
Sam Giancana and other major mob figures. Okay,
he steps in. RFK looked at the logistics. and
told the president, effectively, you cannot sleep
at Frank Sinatra's house. It is a massive security
risk, it is a moral liability, and it will absolutely
kill us in the press. So the president cancels.
At the very last minute. Yeah. And to really
twist the knife, the administration decides the
president will stay at Bing Crosby's house instead.
Oh, that has to sting. Bing Crosby was Sinatra's
massive rival. It was the ultimate humiliation.
Bing Crosby was a Republican. He was the old
guard and he was Sinatra's biggest professional
rival. I can't even imagine Sinatra's reaction.
He was incandescent with rage. He famously took
a sledgehammer and personally smashed up the
concrete of the helipad he had just built. A
sledgehammer. Yes. But here is the thing. He
couldn't unleash his rage on the president of
the United States. That's treason. And he couldn't
attack the attorney general. So he needed a scapegoat.
He attacked the proxy. He blamed Peter Lawford.
He felt Lawford should have fixed it. That he
should have used his family influence to smooth
it over. What could Lawford even do? Nothing.
Lawford tried to explain. He said, Frank, he's
the president. I can't tell him where to sleep.
Right. It didn't matter. Sinatra cut him off
instantly. When you say cut him off, what did
that look like professionally? It was a Soviet
-style erasure. Lawford was slated to star in
the next Rat Pack movie, Robin and the Seven
Hoods. Sinatra fired him immediately and replaced
him with, you guessed it, Bing Crosby. Wow. Just
rubbing salt in the wound. Lawford was banned
from the hangouts. He was completely excommunicated.
Sinatra never spoke to him again except once,
very briefly, years later, when Sinatra's son
was kidnapped. And because Lawford's entire identity
was being the connector, once that connection
was severed, he really had nothing left. Precisely.
He divorced Patricia Kennedy in 1966, so he lost
the White House connection, too. He just spiraled.
The descriptions of his later years in the sources
are really harrowing. They are. He became famous
for being famous drifting through really bad
TV movies, struggling with severe alcoholism
and drug addiction. He was essentially a man
without a country. The notes on his health are
tragic. Kidney failure, liver failure. He died
at just 61. On Christmas Eve, 1984. And even
his death was co -opted by the media machine.
This part is awful. There was a major dispute
over his burial between his widow and the cemetery.
Eventually, his ashes were scattered in the Pacific
Ocean. But his widow invited the National Enquirer
to photograph the scattering. No, that is just
the ultimate indignity. It perfectly encapsulates
his life, unfortunately. He started as the son
of a knight and ended as a photo op for a supermarket
tabloid. He was a man who never built his own
foundation. He built his house on the land of
others. Yeah. And when the landlords evicted
him, he just collapsed. It really highlights
that idea of the system player. Yeah. He played
the game, MGM, the Rat Pack, the Kennedys. But
when the systems rejected him, he didn't have
a core to stand on. Exactly. Now let's look at
the counter argument. Shirley MacLaine. Yes.
Because she was. In that rat pack orbit, she
was basically the only woman they really let
into the inner circle. But her trajectory is
completely different. Shirley MacLaine is the
ultimate case study for agency. Yeah. If Lawford
was defined by association, MacLaine was defined
by pure self -determination. And interestingly,
like Lawford, her story also starts with a physical
issue. The weak ankles. Yes. She was born Shirley
MacLaine Beattie in Virginia. As a toddler, she
had incredibly weak ankles. She would constantly
fall down. So her mother put her in ballet school
at age three. Not to make her a star though,
right? No, not at all. It was strictly as therapy
to strengthen the joint. And that created a monster
in the best possible way. It instilled a military
grade discipline in her. She became obsessed
with dance. She never missed a class. She was
often the tallest in the class, so she actually
danced the male roles a lot. Oh, really? Yes,
which gave her a very different physical presence
on stage, more grounded, less delicate. There
is a famous story where she broke her ankle right
before a performance of Cinderella. She didn't
dance on a broken ankle, did she? She did. She
tightened the ribbons on her toe shoes to act
as a makeshift splint. danced the entire role,
took her curtain call, and then called for the
ambulance. That is insane. But that is the psychological
profile of Shirley MacLaine. The show goes on
because I say it goes on. That sheer grit took
her to Broadway. And this is where we get one
of those classic Hollywood myths that actually
turns out to be entirely true. The understudy
story. It is the ultimate showbiz cliche, but
it happened exactly like they say. It's 1954.
She is in the chorus of the Pajama Game on Broadway,
and she's understudying the lead, Carol Haney.
And Carol Haney gets hurt. Carol Haney injures
her ankle. There's a theme here. And McClane
goes on in her place. And who just happens to
be in the audience that night? Hal B. Wallace,
the legendary producer at Paramount. He was there
to see the show, and he sees this dynamo on stage
with pixie hair and long legs and this incredible
comic timing. He signs her to a film contract
almost immediately. And just a few months later,
she is starring in The Trouble with Harry for
Alfred Hitchcock. For Hitchcock. Talk about a
launch pad. Hitchcock for your very first movie.
But then she also ends up in the Rat Pack orbit.
She's in Some Came Running, and she has a cameo
in Ocean's Eleven. She calls herself the mascot.
How did she survive that boys club environment?
By never playing the damsel. She wasn't a romantic
conquest for them. She always said Sinatra and
Dean Martin never hit on her. They protected
her. So she was just one of the guys. In a very
male dominated environment, she absolutely held
her own. She could drink with them. She could
swear with them. And crucially, she was financially
independent. She wasn't an accessory. She was
a peer. But she wasn't afraid to fight the powers
that be either. I was reading about her lawsuits
in the sources, and I genuinely didn't realize
she was such a legal pioneer in Hollywood. This
is probably her most underrated legacy. In the
old studio system, actors were essentially indentured
servants. If you turned down a role, the studio
would suspend you. And then they would just add
the time of the suspension to the end of your
contract. So you could never leave. Exactly.
You could never leave. It's a hamster wheel.
A legal hamster wheel. McLean actually sued Hal
Wallace, the man who discovered her, to break
that cycle early in her career. Gutsy. But her
biggest legal victory was against 20th Century
Fox. This is the case. Parker v. 20th Century
Fox Film Corp. Parker because she was married
to Steve Parker at the time, right? Yes. And
this case is literally a staple of first -year
contract law classes today. Break that down for
us. What actually happened? She signed a contract
to star in a musical called Bloomer Girl. The
fee was $750 ,000, which was huge money for the
time. Massive. But the studio canceled the film.
But they said, don't worry, we will pay you the
exact same money, but you have to star in this
other movie we are making called... Big country,
big man. A Western. A Western. And critically,
Bloomer Girl was going to shoot in Los Angeles.
The Western was shooting in the Australian Outback.
Big difference. Shirley said no. A musical in
L .A. is not the same job as a Western in the
Australian Outback. You breached the contract.
And the studio presumably said, you're being
difficult. It's the same money. Take the job
or you get nothing. Exactly. And most actors
at that time would have caved. They would have
taken the money and gone to Australia. But McLean
sued. She sued. And the case went all the way
up to the California Supreme Court. Wow. The
court ruled in her favor, establishing the legal
precedent that an employee does not have to accept
inferior or different work to mitigate damages
in a contract dispute. So she forced the studio
to pay her the $750 ,000 for doing absolutely
nothing. Yes. That is a total boss move. It completely
shifted the balance of power in Hollywood. She
proved you could literally punch the studio in
the mouth and survive. Which, speaking of punching,
we have to mention Mike Connelly. We do. The
columnist from The Hollywood Reporter. Yes. He
had been writing all these snarky, negative things
about her contract disputes in the trade papers.
And she didn't just write a strongly worded letter
to the editor. No. She physically marched into
his office, walked right up to his desk, and
punched him right in the mouth. I can just picture
it. That's incredible. It made the cover of the
New York Post. The headline was, Shirley Delivers
a Punchy Line. Of course it was. It just shows
you she wasn't going to be bullied by the press
or the studios. She commanded respect. But then
you have this whole other side of her, the metaphysics,
the spirituality. To a lot of people, especially
in the 80s, she became the lady who talks about
UFOs. Yes. This became a massive part of her
public persona. She wrote these huge bestselling
books like Out on a Limb. Right. She spoke openly
about reincarnation, about trance channeling.
She talked about her past life in Atlantis, where
she claimed she was the brother of a 35 ,000
-year -old spirit. named Ramtha. Ramtha, right.
And the UFOs. She talked constantly about seeing
UFOs at a ranch in New Mexico. She was completely
unapologetic about it. It's easy to chuckle at
the Atlanta stuff now, but looking at it strictly
through the lens of her career and her business,
does this hurt her? Surprisingly, no. In fact,
paradoxically, it might have actually helped
sustain her relevance. How so? While Wofford
was fading away, McLean was evolving. She became
a central figure in the entire New Age movement.
It gave her a platform that had absolutely nothing
to do with Hollywood casting directors. So she
diversified. Exactly. She became a guru. She
was doing seminars. She created a direct relationship
with a new audience that bypassed the studio
gatekeepers entirely. And artistically, she kept
delivering. I mean, she wins the Oscar for Terms
of Endearment in 1983. She does. And look at
that role. Aurora Greenway. A difficult... Prickly,
deeply complex mother. She wasn't trying to be
the cute pixie anymore. She allowed herself to
age on screen and to be unlikable. That takes
artistic bravery. It does, and she just kept
working. Into her 80s and 90s, Downton Abbey.
Only murders in the building. She adapted. She
fought the system when she needed to. But she
also created her own reality, both literally
and spiritually. That just kept her interesting.
So Lawford gets crushed by the system. McLean
fights the system and builds her own world. Right.
Now let's look at Tony Bennett because his path
feels very different again. He's not an aristocrat
and he's not really a Hollywood insider in the
same way the other two were. Not at all. Tony
Bennett, born Anthony Benedetto, was a pure product
of Queens, New York. Yeah. He grew up in deep
poverty during the Depression. His father died
when he was just 10 years old. So he was working
early. He was singing as a singing waiter at
age 13 just to help support his family. But the
defining event for him has to be World War II.
I was actually genuinely shocked reading the
details of his service in the sources. Most people
are. You hear Tony Bennett and you think I left
my heart in San Francisco. You don't think infantry
riflemen in Nazi Germany. It is a really jarring
contrast. Anthony Benedetto was drafted in 1944.
He was assigned to the 63rd Infantry Division,
which was known as the Blood and Fire Division.
That sounds intense. This wasn't the USO tour.
He wasn't back at base singing for the troops.
He was a frontline infantryman during the coldest
winter in recorded European history. The source
material mentions him being in foxholes and facing
88mm guns. Yes. He fought in the direct aftermath
of the Battle of the Bulge. He was digging foxholes
and frozen solid ground while being shelled by
German 88mm artillery. He described it later
as having a front row seat in hell. God. He saw
his close friends killed right next to him. But
the most haunting moment for him was the liberation
of the concentration camp. Koffering? Yes, Koffering
I, which was a sub -camp of Dachau. He was among
the American soldiers who liberated it. What
did he see? He saw the piles of bodies. He saw
the starving, traumatized survivors. He wrote
later that he saw things no human being should
ever have to see. And that exact experience turned
him into a fervent, lifelong pacifist. He said,
this is not life. Every war is insane. There
was another incident within the Army itself that
really shaped him, specifically regarding race.
Yes. You have to remember, the U .S. Army was
still completely racially segregated during WWII.
Right. After the fighting stopped, Bennett was
in the occupying force in Germany. He ran into
a high school friend of his from New York who
happened to be black. They were so happy to see
each other, they went to have Thanksgiving dinner
together in the mess hall. Just two guys from
New York eating dinner? Just two friends. Yeah.
But an officer saw them. And he was absolutely
furious that a white corporal was binding with
a black soldier. He actually walked over, spit
on Bennett's rank insignia, ripped them off his
uniform right there, and demoted him from corporal
to private. For eating dinner with a friend.
Yes. And he was reassigned to graves registration
duties as a punishment. Digging up bodies. Exhuming
mass graves. It was a direct punishment for the
crime of eating dinner with a black friend. That
fury, that sense of profound injustice burned
in him forever. It explains so much about his
later politics, which we'll get to. So he comes
back from this absolute nightmare. How does he
become the Tony Bennett we know? He uses the
GI Bill to study at the American Theater Wing.
And this is a crucial technical point. While
he was there, he learned the bel canto singing
technique. Okay, let's pause right there. What
exactly is bel canto and why does it matter so
much to his story? Bel canto literally translates
to beautiful singing. It is a classical operatic
technique. Most pop or jazz singers sing directly
from the throat. It sounds great. It's raspy.
It's intimate. But it puts tremendous physical
strain on the vocal cords. So it wears out. If
you sing from the throat for 40 years, you will
lose your voice. It's inevitable. Belcanto teaches
you to keep the throat completely open and relaxed
and to support the sound entirely with your diaphragm
and your core muscles. It's structural. Exactly.
It's structural. His teacher told him if you
learn this technique, your voice will last forever.
And it did. It absolutely did. He was singing
with perfect clarity in his 90s because he wasn't
straining at all. He was treating his voice like
a Stradivarius violin. So he has the technique.
He gets discovered by Pearl Bailey. Bob Hope
gives him the stage name Tony Bennett. And then
the hits just start coming. Because of you. Rags
to riches. He becomes a massive star. And then
the monster hit. I left my heart in San Francisco
in 1962. That song was the peak. It won multiple
Grammys. It became his signature tune globally.
But then the culture changed overnight. The Beatles.
The Beatles arrived in 1964. Rock and roll completely
took over the charts. And suddenly the traditional
crooner was essentially extinct. This is the
slump phase. And reading the sources, it sounds
like it was really rough for him. The record
executives really wanted him to change his style
right. Clive Davis at Columbia Records pressured
him relentlessly. He basically told him, nobody
wants your jazz standards anymore, Tony. You
need to record rock songs. You need to be contemporary.
And Bennett hated that. He despised it. There
is a verified story that he actually physically
vomited before a recording session because he
was so disgusted by the material he was being
forced to sing. What were they making him sing?
Songs like Eleanor Rigby, which is a great song,
but he just didn't connect with it. He felt he
was completely selling out his art. And his personal
life was spiraling at the same time, too. Very
badly. By the late 70s, he had no recording contracts.
He had no manager. He was living out in Los Angeles,
severely addicted to cocaine, and the IRS was
trying to seize his house for back taxes. He
was on the brink. He overdosed in a bathtub and
had a literal near -death experience. That is
rock bottom. So how on earth does he get out
of that? He makes a phone call. He calls his
sons. and his son Danny Bennett, who was actually
an aspiring rock musician himself, but had a
brilliant head for business, stepped up. Danny
takes over. Danny took over as his full -time
manager. And he came up with a strategy that
was absolutely brilliant in its simplicity. What
was the strategy? Danny realized that Tony's
problem wasn't the music. The music itself was
timeless. The problem was the audience. The current
audience was literally dying out. So what do
you do? Danny said, we aren't going to change
the music at all. You're going to wear the suit.
You're going to sing the great American songbook.
But we are going to change where you sing it.
So instead of Vegas lounges. He books him on
Late Night with David Letterman. He gets him
a guest spot on The Simpsons. Capital City. Exactly.
And eventually the absolute masterstroke. MTV
Unplugged. That MTV Unplugged album, I remember
that so clearly. It was a massive cultural moment.
It was huge. It's 1994. Tony Bennett walks out
on the MTV stage. He is wearing an immaculate
suit and tie. He looks like everyone's classy
grandfather. And he just stands there and sings,
Steppin' Out With My Baby. And the kids loved
it. The slacker Generation X, the grunge kids
in flannel shirts, they absolutely devoured it.
Why do you think that worked so well? Why did
they connect with him, of all people? Authenticity.
Pure authenticity. He wasn't a 60 -something
guy trying to wear leather pants and pretend
to be a rock star. He was just this cool, classy
guy in a tie singing Gershwin flawlessly. He
didn't try to be young. He just was himself.
In a world of plastic pop, here was a guy who
was the real deal. Exactly. He won the Grammy
for Album of the Year for that record. He beat
out Pearl Jam and Eric Clapton, didn't he? He
did. It is arguably the greatest comeback in
music history. And that momentum carried him
all the way into the modern era with Lady Gaga.
Right. We have to talk about the end of his career,
too. The collaborations with Gaga and the Alzheimer's
diagnosis. He was revealed to the public in 2021,
although he was actually diagnosed back in 2016.
What is truly incredible, neurologically speaking,
is that even with severe memory loss, the music
remained completely intact. How is that possible?
His neurologist actually noted that touring and
performing kept his brain stimulated. The neural
pathways in the brain for musical performance
are entirely different from declarative memory.
So he might forget a conversation, but not a
song. Exactly. He could step onto the stage at
Radio City Music Hall alongside Lady Gaga, maybe
not knowing exactly where he was five minutes
before. But the exact second the piano started,
he knew every lyric, every nuance, every note.
It was muscle memory and soul memory. That is
just beautiful. So we have these three really
incredible lives. But I want to circle back to
something we touched on earlier. Politics. Yes.
Because according to the sources, all three of
them were deeply involved in politics, weren't
they? They were. And it's not just that they
were involved. It's that they took very real
personal and professional risks. But their motivations
for doing so were entirely different. Let's break
that down. We talked about Lawford fundraising
for JFK. That was obviously personal. Right.
Lawford was a partisan. He raised millions of
dollars for the Democratic Party because his
brother -in -law was the candidate. He was tribal.
He was essentially the Hollywood ATM for the
party. But it was fundamentally about family
loyalty and proximity to power. And McLean. She
seems a bit more ideological. Shirley McLean
actually put her entire Hollywood career on hold
in 1972 to campaign full time for George McGovern
against Richard Dixon. I read her agent threatened
to quit over it. He did. And she spent $250 ,000
of her own money on the campaign, which adjusted
for inflation is like $1 .4 million today. Wow.
She was organizing. She was fundraising. She
was writing books about the political process.
She was a true believer in the anti -war movement.
Her politics were deeply intellectual and spiritual.
And then there's Bennett. Bennett's activism
was born directly from his war experience and
that traumatic demotion in the army. He marched
in Selma with Martin Luther King Jr. in 1965.
That was incredibly dangerous at the time for
a high -profile celebrity. Extremely dangerous.
A white civil rights activist who actually drove
Bennett to the airport after the march was murdered
by the Ku Klux Klan later that exact same day.
My God. Bennett knew the stakes. He performed
on a makeshift stage in Montgomery made out of
actual coffins. And years later, he absolutely
refused to perform in apartheid South Africa.
It wasn't PR for him. No. For him it wasn't about
branding. It was a strict moral imperative. He
had seen the concentration camps. He had felt
the sting of racism in his own unit. He simply
couldn't stay silent. It's really interesting
to see how they all lean left politically, but
for slightly different reasons. Just to summarize
what the sources show, Lawford was driven by
family ties, McLean by intellectual conviction,
and Bennett by live trauma. Exactly. And I think
this brings us to the real sort of so what of
our deep dives today. The synthesis. Right. When
we look at these three lives side by side, what
do we actually see? Well, let's look at the scorecard.
Lawford. He ends up sad, isolated, defined completely
by his proximity to others. Lawford is the tragedy
of the association. He defined his entire existence
by who he knew. Sinatra, JFK, the Rat Pack. When
those people cut him off, he literally ceased
to exist in his own mind. He was a satellite
that lost its planet. And McLean. McLean is the
individualist. She frankly didn't care if the
system liked her. She sued the system. She punched
the critics in the mouth. She created her own
philosophy. She survived because her sense of
self came from inside. Even if that inside was
filled with Atlantean spirits and UFOs. Exactly.
It was hers. It belonged to her, not a studio.
And Bennett, where does he fit? Bennett is the
purist. He believed in the art. He believed in
that Bel Canto technique he learned in the 40s.
He believed that if he just kept doing the thing
he was genuinely good at with total integrity,
eventually the world would come back around to
him. And he was right. He was completely right.
He outlasted the trends by simply ignoring them.
It's the art versus the celebrity. Lawford became
famous for being famous. Bennett became a national
endowment for the arts jazz master and an accomplished
painter with his actual artwork hanging in the
Smithsonian. McLean became an author and a legendary
actress. It really makes you think about this
whole concept of rebranding. We talk about it
all the time now in modern culture. But Bennett
didn't rebrand. He stayed exactly the same. The
world rebranded around him. That's fascinating.
Lawford couldn't rebrand because he had no brand
other than Kennedy and Law. And McLean rebranded
constantly because she was just endlessly, relentlessly
curious. That is a great way to put it. One thing
that really stands out to me looking at all three
is the role of resilience. All three of them
faced a distinct moment where the industry basically
said, we are done with you. Yes. For Lawford,
it was the Sinatra snub. He accepted the verdict
and he just withered away. For McLean, it was
the contract disputes. She actively fought back.
For Bennett, it was the... rock and roll era,
and he just endured it. It really comes down
to what you are anchored to in life. Are you
anchored to other people's approval, or are you
anchored to your own craft and your own deeply
held beliefs? Authenticity is such a buzzword
now, but Tony Bennett was the living, breathing
embodiment of it. Shirley MacLaine is the embodiment
of fearless curiosity. And Peter Lawford. He
is a stark, cautionary tale of what happens when
you build your house on someone else's land.
Precisely. Competence is the only true security.
So here is a final thought to leave you with
today. We live in an era of influencers. We do.
People who are famous strictly for who they know,
what parties they go to, who they're seen with
online. It feels very Peter Lawford. It does
feel like that. It is a very fragile kind of
thing. But Tony Bennett and Shirley MacLaine
remind us that true longevity, the kind of career
that lasts 70, 80, 90 years, requires something
else entirely. It requires a tangible skill,
a real belief, a solid core. Absolutely. If the
Internet just turned off tomorrow and you lost
all your followers and your famous friends stopped
calling, who would you be? Would you crumble
like Lawford or would you tighten ballet shoes
or pick up the microphone and just keep going?
That is the ultimate question. Thanks for diving
deep with us. We'll see you next time.