Welcome back to the Deep Dive. Today, we've got
this huge stack of sources, interviews, articles,
liner notes, and we're going to try and map out
the career of, well, a true American genius,
Paul Simon. And restless is the word we have
to just keep coming back to. I mean, we're not
just looking at a successful songwriter. That's
that's underselling it. Yeah. We're talking about
someone who kept changing the map of popular
music. Yeah. over and over again from, what,
1956 all the way to today. Exactly. So our mission
here is to really get into how he managed that.
How does a kid from Queens singing doo -wop become
the voice of 60s folk? And then he pivots to
become this global music synthesizer, pulling
in sounds from South Africa, from Brazil. And
that's the real question, right? What is that
creative drive? Is he just restless? Is he constantly
searching for something new or is he just allergic
to repeating himself? And we should probably
just lay out the credentials right away because
the success is just staggering. We're talking
16 Grammy Awards. And the big one album of the
year. He's one of only, I think, eight artists
to win it multiple times as the main artist.
First for Still Crazy after all these years.
That incredibly introspective New York kind of
album. Right. And then for Graceland. which is
this massive global explosion of sound. And you've
also got the double induction into the Rock and
Roll Hall of Fame. First with Simon and Garfunkel
in 90, then solo in 2001. It's like two separate
legendary careers. It really is. Okay, so let's
try to unpack this. How does a 12 -year -old
writing his first songs become this global force?
And why does his newest work, Seven Psalms, which
is so meditative, suggest that even now he's
just... He's not done. Let's start at the very
beginning. In Queens. So to get the foundations
of Paul Simon, you really have to start in New
York City. He was born in Newark, New Jersey
in 1941, but the family moved to Queens in 45.
Hungarian Jewish roots. And that background is
so crucial. His family was musical, but a very
different kind of musical. His dad, Louis Simon,
was a professional bass player, a band leader.
Lee Sims was his stage name. Right, Lee Sims.
So he's coming from this world of big bands,
dance music. And his mom, Belle, was a schoolteacher.
But it's that move to Kew Gardens Hills in Queens
that really shapes him. And there's this great
observation we found from Donald Fagan of Steely
Dan. He kind of grew up in a similar world. Yeah,
and Fagan said that Simon's childhood was like
that of a certain kind of New York Jew where
music and baseball were just everything. Why
those two things specifically? Well, Fagan's
point, and Simon's basically agreed with it,
was that for kids like them, Assimilating was
complicated. So they gravitated to black music,
you know, doo -wop, R &B and baseball as this.
This alternative culture. A way to find an identity
outside of the mainstream. Exactly. It was a
place to belong that wasn't their parents' classical
music world or the sort of white pop music of
the time. Which totally clicks when you hear
Simon talk about hearing early rock and roll
for the first time. Songs like G by the Crows.
Earth Angel, yeah. He said he tried to explain
to his dad how powerful those sounds were. And
his dad, this accomplished musician, just...
He didn't buy it. That's how Simon put it. And
that little rift, that's kind of the start of
everything. He's rejecting his dad's sophisticated
world for this raw energy he's hearing on the
radio. And pretty quickly, he finds a partner
in that search, Art Garfunkel. They meet when
they're 11, 1953. They were in a school play
together, Alice in Wonderland, by 13. They're
singing together all the time. And writing. Simon
wrote his first song, The Girl for Me, when he
was 12 or 13. And he said it was a neighborhood
hit. They played it everywhere. I love this detail
from the sources because Simon didn't know how
to write music down yet. His dad, Louie, wrote
out the chords and the words for him. And that
piece of paper is now in the Library of Congress.
The first copyrighted Simon and Garfunkel song.
written down by the very musician whose style
he was rebelling against. That's incredible.
So that leads to their first record, right? Hey,
schoolgirl. 1957. Yeah. They're still teenagers.
They call themselves Tom and Jerry. After the
cartoon. Yep. And it actually charts. It gets
to number 49 on Billboard. A little taste of
success right out of the gate. But that Tom and
Jerry phase, that whole period between 57 and
64, he was working constantly. Oh, he was a hustler.
He recorded over 30 songs under all these different
names. Yeah. Jerry Landis. Paul Kane. He was
trying on different identities. Completely. As
Jerry Landis, he even had another small hit,
The Lone Teen Ranger, which barely scraped the
charts at number 97. He was just learning the
craft from every angle. So the real beginning
of Simon & Garfunkel, the brand, comes in 1964
with Columbia Records. Right. They audition for
Clive Davis. He signs them. And the label makes
this decision to just use their last names. Simon
says it was the first time that it happened in
pop music. It made them sound serious. More like
poets or authors than pop singers. Exactly. So
they released their first album Wednesday morning,
3 a .m. in late 64. It's a very traditional acoustic
folk record. And it completely bombs. Totally
tanks. Sells nothing. The sound of silence is
on there, but it's quiet. It's acoustic. No one
cares. And the failure is so bad it breaks them
up. Garfunkel goes back to college. To study
math, of all things. And Simon, who had done
a bit of law school, decides he's done. He backs
up and moves. And here's where it gets really
interesting, because that failure leads to this
U -turn that changes everything. He moves to
London in 1965. And he finds his people there,
in the folk clubs. He said there was no place
to play in New York City for what he was doing.
But in London, they got it. This wasn't just
a break, though. This was like... His graduate
school for songwriting. Totally. He said the
experience was very powerful. He's soaking up
all this English folk tradition. And crucially,
he meets the guitarist Martin Carthy. And we
really need to pause on Martin Carthy because
this is a huge deal. It's everything. Before
this, Simon was mostly a strummer. Carthy teaches
him this complex finger -picking style where
you're playing the melody, the bass, the rhythm
all at once on one guitar. You can hear it all
over their later stuff. Scarborough Fair. The
boxer. It's the absolute foundation of that sound.
It turns him from a songwriter into a true composer
for the guitar. He's writing classics over there
like Homeward Bound and I Am A Rock. He's basically
building this new, sophisticated sound. But the
thing that brings him back to America and to
stardom happens completely without his permission.
It's one of the great stories in music history.
The Sound of Silence remix. So while Simon is
playing to like... 50 people in a London club,
some DJs back on the East Coast start playing
the original acoustic version from the album
that flopped. Yeah, in Boston and Florida, it's
getting some traction. And their producer, Tom
Wilson, he notices. And Wilson, who had worked
with Dylan, he sees an opportunity. He takes
their original quiet track. And just dubs a full
electric band over it. Electric guitar, bass.
drums. He turns it into a folk rock anthem. And
the key thing is he does it without telling them.
Can you imagine? Simon said he was horrified
when he heard it. He thought it ruined the song.
But it didn't matter what he thought. The single
goes straight to number one in the U .S. in early
66. And suddenly they're stars. They have to
get back together. That one unauthorized remix
launches their entire career. It leads to Sounds
of Silence, Parsley, Sage. Rosemary in Time,
Bookends, all those classic albums. They pretty
much become the voice of the late 60s. I mean,
Mrs. Robinson from The Graduate. And that title
is another great story. Simon was apparently
toying with calling it Mrs. Roosevelt. Seriously?
Yeah. Until the director, Mike Nichols, just
said, don't be ridiculous. It's Mrs. Robinson.
It's that classic tension between Simon's, you
know. literary ideas and the need for a pop hook.
And then at the absolute peak of their fame,
it all falls apart after Bridge Over Troubled
Water in 1970. Which was a monster album. That
title track alone, the influences are just incredible.
The main line comes from a gospel song, Mary,
Don't You Weep. By the Swan Silvertones, yeah.
And the melody, the actual melody is based on
a Bach chorale. It's this perfect synthesis of
high and low culture. But even with all that
success, the relationship was just done. They
split. And our sources say that Simon told Clive
Davis it was over at the urging of his first
wife, Peggy Harper. Which, again, shows you how
much his personal life was always tangled up
in his professional one. It wasn't just an artistic
split. So that's it. The duo is over. And now
he has to figure out who he is all by himself.
Right. And his first move is... Kind of surprising.
Yeah, in 1970, he actually starts teaching. He
taught songwriting for a little while at NYU.
Which is pretty wild to think about. He's just
come from being in the biggest band in the world,
and now he's in a classroom. But he was very
realistic about it. He said, you can't teach
someone how to write a song. He was more interested
in the process and helping students avoid the
mistakes he made. He was always a student of
the craft, even when he was the one teaching.
His first solo album, just called Paul Simon,
comes out in 72, and the critics love it. It's
the moment he proves he can do it alone. And
right away, he starts pushing the boundaries.
This is where you see the first real hints of
his interest in world music, the song Mother
and Child Reunion. Which was a top five hit.
He recorded that in Kingston, Jamaica, with Jimmy
Clips Band. That's a huge deal for a mainstream
folk rock guy in 1972. It was a clear signal
that he wasn't going to just make another folk
record. The album also had Mean Julio, Down by
the Schoolyard, another big hit. He was on a
roll. Yeah, and then there goes Ryman Simon in
73. Keeps it going. You get Kodachrome and Loves
Me Like a Rock. That one also had something so
right, which was a really open tribute to his
wife, Peggy. He was putting his whole life into
these songs. He was. And that's why the next
album feels so different. The mood just darkens.
Still crazy. After all these years, 1975, this
comes right after his divorce from Peggy. And
you can hear it all over the record. It's cynical.
It's full of this midlife New York anxiety. The
music is really slick and polished, but the lyrics
are, they're bruised. But it was huge. It's his
only solo number one album on the Billboard charts,
and it wins the Grammy for Album of the Year.
It proved his strength was turning that personal
pain into these incredibly sophisticated, relatable
pop songs. And the biggest hit from it, 50 Ways
to Leave Your Lover, is like the ultimate example
of that. It's this jaunty, catchy tune about
the end of his marriage. A total breakup anthem
disguised as a pop song. Classic Simon. So in
the late 70s, he starts branching out even more.
He gets into acting. Yeah, he has that great
role as the sleazy record producer Tony Lacey
in Annie Hall, Woody Allen's movie. He was great
in that. And he started hosting Saturday Night
Live a lot. He was a fixture on early SNL. But
the one everyone remembers is the Thanksgiving
show in 1976. Did the turkey suit. The turkey
suit. Yeah. He comes out to sing, still crazy
after all these years, wearing this giant, ridiculous
turkey costume. And he just, he can't do it.
He stops mid -song. He stops, tells the audience
how embarrassing it is, and then walks off stage
yelling at Lorne Michaels. It's this perfect
moment of this serious artist clashing with the
absurdity of television. Then he dives into making
a movie himself, One Trick Pony, in 1980. He
wrote it, starred in it, and did the soundtrack.
It was a very personal project about a musician
struggling in the industry. The album had a great
single late in the evening, but the whole thing.
It didn't really land commercially. And that
kind of dip in his career sets the stage for
something massive. The reunion, the 1981 concert
in Central Park with Garfunkel. A huge, huge
event. The live album, the TV special, it was
everywhere. And it immediately got them talking
about making a new studio album. Which is where
it gets complicated again. That reunion album
was supposed to be Hearts and Bones. But it didn't
end up that way. No. They start recording, the
old tensions flare up, and Simon eventually just...
erases Garfunkel's vocals from the tapes and
releases it as a solo album. Wow, that's a bold
move. And it had huge consequences. Artistically,
Hearts and Bones is now seen as a masterpiece.
It's incredibly well -written, confessional.
A lot of critics call it one of his best. But
at the time? At the time, it was his biggest
commercial failure. People were expecting a Simon
and Garfunkel reunion, and they got this very
intense personal solo record instead. It just...
It confused everyone. That album had the late
great Johnny Ace, which is this tribute to Johnny
S. and John Lennon. And it features this haunting
orchestral piece at the end by the composer Philip
Glass. Which is another example of him pushing
boundaries, right? Bringing in this avant -garde,
minimalist composer into a pop song. Absolutely.
It shows he was still reaching, still trying
to blend these really different worlds, even
if the audience wasn't quite there with him.
And so much of that album was about his relationship
with Carrie Fisher. Yeah. Their whole story is
woven through it. They got married in 83, divorced
in 84, but were on again, off again for years.
The title track, Hearts and Bones, is about them.
The song Graceland started as a reflection on
their relationship. She later said She Moves
On was about her too. He was just constantly
processing their life through his art. He was.
And you could argue that the commercial failure
of that brilliant personal album is what freed
him up to do something completely radical next.
He had nothing to lose. Which brings us to Graceland.
Yeah. By the mid -80s, his career was kind of
in a weird place. Hearts and Bones was a critical
gem, but a commercial dud. He needed something
to shake things up. And he found it on a cassette
tape. A bootlegged cassette, yeah. It was South
African street music, Wimbaconga. And he was
just completely captivated by the rhythms. So
he doesn't just borrow the sound. He goes all
in. He goes all in. He travels to Johannesburg
to record with the musicians there. People like
Ladysmith Black Mambazo, the bassist Bakithi
Kamalo. he immerses himself completely. And the
way he wrote the songs was different for him,
right? Totally different. He didn't show up with
finished songs. He would just improvise melodies
over these amazing rhythm tracks they were laying
down. He said the word Graceland just came to
him, even though he wasn't planning to write
about Elvis. He was letting the music lead the
word. Exactly. The result was this. This incredible
fusion. You have this very literary New York
sensibility layered over these joyful, complex
African rhythms. One critic called it a double
vision. That's a perfect way to put it. It's
pop music you can dance to, but it's also got
all this depth and complexity. And it was a monster
hit. It sold, what, 16 million copies worldwide.
It won the Grammy for Album of the Year. It completely
resurrected his career on a global scale. But
this massive success immediately gets tangled
up in a huge political controversy. Oh, yeah.
This raises that really important question about
art and politics. How do you separate the creation
from the context it was created in? So the issue
was the cultural boycott against South Africa's
apartheid regime. Right. The world was trying
to isolate South Africa to pressure them to end
apartheid. And by going there to record. Simon
was seen by many as breaking that boycott. People
like Billy Bragg were very critical. The African
National Congress, the ANC, they protested it.
It was a serious high stakes debate. And Simon's
defense was very specific. He argued he wasn't
there to make money for the regime. He paid the
black artists extremely well, gave them royalty
points. He saw it as collaboration, not exploitation.
Exactly. He was amplifying their voices on a
global stage. And it was so complicated that
even anti -apartheid groups were divided. The
UN's committee actually supported the album in
the end because it did so much to showcase black
South African musicians. But the ANC still held
that he broke the protocol, which was a big deal.
It was. He was even briefly put on a UN blacklist.
It was a real firestorm. So how did it all get
resolved? Well, the ultimate resolution came
a few years later in 1992. Apartheid was ending.
Nelson Mandela was free, and Mandela himself
invited Simon and his band to come play in South
Africa. Wow! An endorsement from Mandela himself!
That pretty much ended the controversy. It was
an affirmation of the album's positive cultural
legacy. And he didn't stop there with the world
music exploration. No way. In 1990, he released
The Rhythm of the Saints, and this time he was
diving into Brazilian music. The sound on that
album is a bit different though, right? A little
more introspective. Yeah, it's darker, more rhythmically
complex. He's working with these incredible Brazilian
percussion groups like Elodum, the lead single.
The Obvious Child is just driven by these massive
drums. And it was another big success. It proved
Graceland wasn't a fluke. This was his new direction.
It was. And all that success led to another huge
concert back in Central Park in 1991. But this
time, no Garfunkel. No. This was his show. Him
and his huge band of African and South American
musicians, half a million people showed up. He
said later, that concert was the most memorable
moment in my career. It was the ultimate validation
of this whole global journey. Yeah, moving into
the mid -90s, he takes what might be his biggest
risk ever. And it leads to his biggest failure.
Broadway. He decides to write a musical. The
cake man. And he collaborates with a Nobel Prize
winning poet, Derek Walcott. I mean, the pedigree
was insane. It was this passion project he worked
on for years. What was the story about? It's
the true story of Salvador Agron, a Puerto Rican
teenager who committed two murders in New York
in 1959. So I'm going to remember this story
from when he was a kid. It was about immigration,
youth, crime. Very heavy themes. And it was a
disaster. A complete commercial disaster. The
critics hated it. It closed almost immediately
and it lost something like $11 million. And the
album of songs from the show was the first solo
album of his career to not even make the top
40. It was a brutal flop. But what's interesting
is even then, some critics praised the music
itself. One called the score Bewitching. It was
this blend of doo -wop and Latin rhythms. Just
maybe too complex for a Broadway audience at
the time. So how does he bounce back from a failure
that big? He goes back on the road. And not just
any tour. In 1999, he tours with Bob Dylan. Two
absolute legends on one stage. Exactly. It was
a huge event. And it just instantly changed the
narrative. The failure of the Cape Man started
to fade and he was back to being Paul Simon,
the icon. And he keeps experimenting. In 2000,
he releases You're the One, which has these North
African grooves. Then in 2006, he works with
Brian Eno on the album Surprise. And that Eno
collaboration is really key. Eno brings in all
these electronic textures, this ambient sound.
It's a very modern sounding record with songs
about 9 -11 and the Iraq war. It shows he's still
engaged, still trying to find new sonic talents.
Always. And he's still listening to new things.
His 2016 album, Stranger to Stranger, has him
working with an Italian EDM artist called Clap.
How did he even find him? His son, Adrian, introduced
him to the music. It just shows he's never stopped
being curious, never stopped searching for that
next sound. So in 2018, it really felt like the
end of the road. He announces his farewell tour.
Yeah, the Homeward Bound tour. He said he was
tired of being away from his family and his longtime
guitarist Vincent Nguini had passed away, which
hit him hard. He played his final show in Queens.
It felt like a perfect bookend. But you can't
really retire the creative impulse, can you?
Apparently not. That same year, he releases an
album called In the Blue Light. And it's not
new songs. What is it? It's re -recordings of
his own lesser -known songs. He went back into
his own catalog and reimagined them with new
arrangements, new harmonies. It's like he was
curating his own legacy. And then just last year,
in 2023, something else entirely. Seven Psalms.
This one is just, it's on another level. It came
to him in a dream. A dream. Yeah, he said a voice
in a dream told him, you were meant to be working
on a piece called Seven Psalms. So he did. It's
this 33 -minute continuous piece of music. It's
acoustic, meditative. It feels like a prayer.
It's so far from pop music. And the sounds he
used. I read he was using amplified wine glasses
to create a sound like church bells. Just always
experimenting. But with the release of that album
came some really tough news. His hearing. Yeah,
he revealed that he lost most of the hearing
in his left ear. Which, for a musician, I mean,
that's just devastating. You would think that
would be it. You would think. But he said the
creative spark from Seven Psalms was so strong,
he's now planning a duets album with his wife,
Edie Brickle. And he's even working on another
musical. He just can't stop. And he's going back
on tour. Back on tour. He announced the Quiet
Celebration Tour for 2025. But this time, it's
all smaller venues, intimate spaces. It's impossible
to talk about his work without talking about
the people who inspired it. His personal life
is all over the songs. Absolutely. His three
marriages are like a roadmap through his catalog.
His first wife, Peggy Harper. Something so right
is about the good times. And then a later song,
Train in the Distance, is this incredibly poignant
look back at their divorce. And then of course
Carrie Fisher. That whole tumultuous iconic relationship.
I mean their road trip inspired the song Graceland.
She confirmed that She Moves On is about her.
He turned their chaos into art. And his current
wife, the singer Edie Brickell, they've been
married since 1992. And it's this incredible
musical family. All four of his kids are musicians.
And now he and Edie are finally planning to make
a record together. It's a beautiful full circle
moment. Beyond the music, though, he's also built
this incredible philanthropic legacy. Yeah. The
Children's Health Fund, which he co -founded.
Yeah. It started with this idea of putting medical
clinics on buses to bring health care to kids
in underserved areas like the South Bronx. And
that's grown into a. huge national organization
now. It has. And what's really interesting is
his philosophy behind giving. He became a big
supporter of something called effective altruism.
Which is basically the idea of using data and
evidence to figure out where your charitable
donation can have the biggest possible impact,
right? Exactly. It's not just about giving. It's
about giving smart. And that is so perfectly
Paul Simon, applying that same restless analytical
genius he brings to music to the act of doing
good in the world. So when you try to sum all
this up, you have this career that starts with
an accident. I mean, if Tom Wilson doesn't remix
the sound of silence, who knows what happens?
Who knows? He might have stayed a folk singer
in London. That moment just throws him into the
pop machine. And the rest of his career is this
constant negotiation between his own artistic
instincts and the pressures of fame. He goes
from being this very American folk voice to becoming
a pioneer of global music with Graceland. He's
always chasing a new sound, terrified of repeating
himself. And now in this latest phase, he's chasing
something else, something more spiritual, more
internal, with seven psalms. It's almost like
he's gone from a global rhythm to a cosmic one.
It all comes back to his process, which he's
always said is music first. The rhythm and the
melody come, and then he has to find the words
to fit inside it. The music leads the way. It
always has. So that brings us to this final thought.
He's coming back to the stage in 2025 with this
quiet celebration tour. Small venues, intimate
shows. And this is the guy who played to half
a million people in Central Park. He's deliberately
trading that massive scale for intimacy. So what
does that tell us about the end of this journey?
Is the ultimate goal for the Restless Explorer
not to conquer the whole world, but to find one
perfect quiet room? Something to think about.
We'll catch you next time for the deep dive.