Welcome back to the Deep Dive. Today we are clearing
the decks. Usually we tackle a specific event,
a scientific breakthrough, maybe a historical
mystery. Yeah. But today we are looking at a
human being. Although, frankly, after reading
through this stack of sources, I'm starting to
wonder if human being is too small a category.
It feels inadequate, doesn't it? We are talking
about a figure who... didn't just participate
in his field, he dismantled it. He took the American
musical theater, stripped it down to the studs,
looked at the rusty wiring. And rewired the entire
thing to run on a completely different power
source. That's it, exactly. We are, of course,
talking about Stephen Sondheim. And I want to
be clear right off the bat, this isn't just a
greatest hits episode. We aren't just going to
list the songs you know. No, no. The mission
today is to unpack the mind that created them.
Because the more I read, the more I realized
that Sondheim wasn't just a composer. He was
a mathematician. He was a puzzle addict. He was
a structural engineer who just happened to build
with music instead of steel. That is the perfect
framing. I mean, if you look at Broadway before
Sondheim, the Rogers and Hammerstein era, and
then you look at it after, they look like two
different planets. Totally different. And Sondheim
is the gravitational force that caused that shift.
And just to set the stakes for anyone who might
only know him from a movie adaptation or two,
the hardware this man collected is absurd. It's
a heavy trophy shelf. eight Tony Awards, which
is more than any other composer, plus a special
Tony for Lifetime Achievement. And that's just
the start. Oh, yeah. Eight Grammys, an Academy
Award, five Olivier Awards in the UK, the Kennedy
Center Honors, and the Presidential Medal of
Freedom. It's a list that just screams institution.
But the irony, which I hope we get into, is that
he spent most of his career feeling like an outsider.
Constantly. He reinvented the musical to tackle
subjects that, you know... No one thought belonged
on a stage. Assassins. Cannibalism. The crushing
ambivalence of modern marriage. Exactly. He took
a medium that was historically about escapism,
you know, Oklahoma, where the corn is as high
as an elephant's eye, and he dragged it kicking
and screaming into the psychological shadows.
Right. But to understand how he did that, though,
we have to look at where he came from. And I
have to say, the source material on his childhood
is... Well, it's harrowing. It really is. It
reads like a gothic horror story set on the Upper
West Side of Manhattan. So let's go back. It's
1930, New York City. Wait, Stephen is born to
affluent Jewish parents. They're in the garment
industry, very successful. And he grows up in
the San Remo on Central Park West. Which, if
you know New York architecture, is one of the
most prestigious, beautiful buildings in the
city. Twin towers, views of the park. On paper,
Stephen Sondheim won the lottery. He's living
in a palace. But the emotional reality inside
that palace was a vacuum. His parents divorced
when he was young, and his father left him in
the custody of his mother, Etta Janet. And she
went by the nickname Foxy. Foxy. And that nickname,
Foxy, seems to cover a very sharp, very predatory
nature. The relationship was, by all modern definitions,
psychologically abusive. The sources suggest
she projected all the rage she felt toward her
ex -husband directly onto Stephen. It was this
really disturbing dynamic where she would, like,
belittle him constantly, but also kind of flirt
with him. It's just, it's deeply uncomfortable
to read about. Yes. She used him as a substitute
for the absent father, someone to berate, but
also someone to demand attention from. It was
confusing and so damaging. But there is one specific
detail in the notes that actually made me gasp.
It involves a letter. I know exactly the one
you're talking about. This wasn't when he was
a kid. This was when he was an adult, right?
He was in his 40s. He was about to go into heart
surgery, a serious operation. And the night before
the surgery, his mother, Foxy, wrote him a letter.
And what did it say? In this letter, she explicitly
stated that her only regret in life was giving
birth to him. Oh, my God. Can you imagine you
are facing a life -threatening surgery and your
mother hands you a note saying, essentially,
I wish you didn't exist? It's just... It's devastating.
And it explains so much about his work, about
the themes of isolation and the desperate need
for connection. He essentially estranged himself
from her for nearly 20 years after that. When
she died in 1992, he didn't go to her funeral.
He did not. So you have to picture this. A brilliant,
wealthy, incredibly isolated boy living in this
big, empty apartment, trying to make sense of
a world that feels hostile. And when you are
that isolated, you become an observer. You watch,
you listen. And that leads us to this spark.
He's nine years old and he sees a show called
Very Warm for May. And this is such a telling
detail about his brain. Most kids go to their
first musical and they are dazzled by the star
or the costumes or the big tap dance number.
Right, the spectacle of it all. But Sondheim
didn't care about that. He remembers a specific
moment where a butler on stage was dusting a
piano. A butler dusting a piano? Yes. The butler
dusted the keys and the piano made a sound. It
tinkled. And Sondheim, as a nine -year -old,
found that specific theatrical mechanism. Why
that? What was so thrilling about it? Because
it wasn't magic. It was a machine working. It
was cause and effect. He saw that theater was
a constructed reality, and he wanted to know
how the construction worked. He wanted to see
the gears turning. So you have the trauma, which
creates the observer, and you have the spark
of interest in the mechanics of it all. Now you
need the guide. The teacher. And this part of
the story is almost Dickensian. The lonely boy
finds a surrogate father. And it just so happens
that the surrogate father is literally the most
famous man in American theater. You couldn't
write this in a script. It would feel too convenient.
Sondheim becomes best friends with a kid named
James Hammerstein. Jimmy. Jimmy Hammerstein.
And Jimmy's dad is Oscar Hammerstein II, the
man who wrote Oklahoma, South Pacific, The Sound
of Music, the absolute titan of the Golden Age.
And they were neighbors in Pennsylvania, right?
That's how it started. That's right. Sondheim's
mother bought a farmhouse out there, which happened
to be near the Hammersteins. And Oster saw this
lonely, brilliant kid and basically took him
under his wing. He became the father Sondheim
never had. Absolutely. But, and this is crucial,
it wasn't a pat on the head, good job kid kind
of mentorship. This was a boot camp. I love the
story about the first musical Sondheim wrote
by George. He's what, a teenager? He's 15. He
writes a musical at his prep school, the George
School. He thinks it's fantastic, the best thing
ever written. Of course he does, he's 15. And
he brings it to Hammerstein and says, very boldly,
I want you to treat this like a professional
manuscript. Don't look at me as your son's friend.
Judge it as if you don't know the author. Wow.
That is a dangerous thing to ask a legend. Please
critique my high school play, Mr. Hammerstein.
It is. And he got exactly what he asked for.
Hammerstein read it, sat him down, and said,
it's the worst thing I have ever read. Ouch.
That is the moment most people would quit. They'd
go into accounting. Probably. But Hammerstein
followed it up. He said, I didn't say it wasn't
talented. I said it was terrible. And then, this
is the gift, he spent the entire afternoon, hours
and hours, going through the script page by page.
Line by line. He explained why the songs were
wrong for the characters. Why the structure collapsed
in the second act. Why the opening number didn't
set the tone or introduce the world properly.
Sondheim later said he learned more in that one
afternoon than most songwriters learn in a lifetime.
It's so interesting because Hammerstein's style
is very sincere, very open -hearted, you know,
climb every mountain, you'll never walk alone.
Full of hope. Exactly. And Sondheim's style became
very cynical, urban, and neurotic. But the craft,
the architecture of the songs, came directly
from Hammerstein. Exactly. Hammerstein taught
him how to build a boat. Sondheim just decided
to sail that boat into much darker, stormier
waters. But the construction methods, that was
all Oscar. Let's talk about the curriculum. Because
Hammerstein didn't just say, go write more. He
gave him a specific syllabus. It reminds me of
the way a classical painter gets trained, you
know, copying the masters before you paint your
own stuff. It was incredibly structured. It was
a four -step process. First, he told him to adapt
a play he admired. Okay, why that? Because if
the play is already good, your job is to not
break it. It teaches you how to translate a solid
existing structure into music, how to find the
moments that should sing without ruining the
architecture. Sondheim picked a play called Beggar
on Horseback. Right. Okay, so that's assignment
one. What's two? Assignment two. Adapt a play
you think is flawed. He picked one called Hytor,
and this goal is much harder. Because now you
have to fix it. Now you're not just translating,
you're problem solving. Can you use music to
fix the narrative problems? Can a song bridge
a logical gap that the dialogue couldn't? Can
you make a weak character stronger with the right
ballad? That's fascinating. It's like musical
dramaturgy. What was number three? Adapt a source
that wasn't a play. A novel or a short story.
And he chose P .L. Travers' Mary Poppins. Wait,
Mary Poppins? Like Chim Cherry? No, no, this
was years and years before the Disney movie.
And totally different in tone. But adapting a
novel is the hardest task of all. Because there's
no built -in structure. None. A novel is internal.
It's narration and thought. It doesn't have scenes
or dialogue structures ready to go. You have
to invent the entire dramatic architecture yourself.
You have to decide what's a scene, what's a song,
what gets cut. All of it. And finally, assignment
four was to write a completely original piece,
which became a show he called Climb High. And
the amazing thing is, none of these were ever
professionally produced, right? Not at the time,
anyway. No, they were for the drawer. They were
his private conservatory. Can you imagine the
discipline required to write four full musicals
just for practice, just for the exercise? Most
people struggle to finish one. It's staggering.
But his education didn't stop there. He heads
off to Williams College, and this is where the
math part of his brain really gets fed. We have
to talk about his teacher there, Robert Barrow.
Barrow is the unsung hero of the Sondheim story.
He was a music teacher at Williams, and Sondheim
described him as very dry, not a showman at all.
But Sondheim loved him because Barrow demystified
music. How so? What does that mean? Well, there's
a tendency to treat artistic talent as this mystical
thing. An angel whispers in your ear and a melody
comes out. Barrow said, He taught Sondheim that
music is logic. It's physics. That's a system.
It's a system with rules. You have leading tones
notes that desperately want to resolve to other
notes. You have diatonic scales. You have chord
progressions that create tension and release.
For Sondheim, this was an aha moment. He realized
art is something you can work out. It's not just
inspiration. It's not magic. And that was empowering.
He said it made him realize that talent is just
a developed aptitude. You can work at it. You
can get better through practice and analysis.
So Barg is in the logic. Then he graduates and
goes to study with Milton Babbitt for the advanced
class. Right. And Babbitt was a serious capital
C composer, an avant -garde guy, very modern.
He was into serialism, atonal music stuff that
can sound like random noise to the untrained
ear. Not exactly show tunes? Not at all. But
what he did with Sondheim was fascinating. They
would spend hours just analyzing music, but not
just Beethoven and Mozart. They analyzed show
tunes. This I love. Taking a catchy Rogers and
Hart tune and treating it with the same seriousness
as a symphony. They would take a song by Jerome
Kern, who wrote Old Man River, and put it under
a microscope. They'd analyze it with the same
rigor as Mozart's Jupiter Symphony. They looked
at how Kern could take a tiny musical motif,
maybe just three or four notes, and spin it out,
develop it, turn it upside down, and build an
entire complex melody without it ever getting
boring. That became Sondheim's mantra. It's the
key to his entire musical language. If you listen
to Sweeney Todd or Into the Woods, you realize
the whole score is built out of these tiny little
musical cells that just keep rearranging themselves.
He isn't writing 50 different melodies. He's
building a skyscraper out of three kinds of bricks.
And Babbitt apparently refused to teach him a
tonality. He did. Sondheim wanted to learn the
really out there stuff, and Babbitt told him,
you haven't exhausted the resources of tonality
yet. In other words, master the rules before
you break them. Precisely. So let's reset the
board. He's got the Hammerstein training in storytelling.
He's got the Barrow and Babbitt training in musical
logic and structure. He is, what, 25 years old?
Yeah, mid -20s. He is ready to conquer Broadway.
He wants to be a composer, lyricist. He wants
to do it all. And nobody will let him. This is
the lyricist trap. It is. This is the 1950s.
Producers wanted sure things. They wanted known
names. They didn't want a 25 -year -old kid writing
the music. They barely trusted him with lyrics.
He had a false start with a show called Saturday
Night. His first professional gig. It was supposed
to be. Music and lyrics by him. It was set to
open in 1954, but then the producer, Lemuel Ayers,
died suddenly. The whole thing just collapsed.
It didn't actually get produced until, what,
the year 2000? Yeah, decades later. He called
it his baby pictures. So he's broke, he's living
in his father's dining room, he's writing for
the TV show Topper to make ends meet, and he's
frustrated. And then he goes to a party. A chance
meeting with the playwright Arthur Laurence.
And Laurence says he's working on a modern version
of Romeo and Juliet with Leonard Bernstein. West
Side Story. The Monolith. But here's the thing
that people forget, or maybe never knew, Sondheim
didn't want to do it. That sounds insane to us
now, turning down West Side Story. But you have
to see it from his perspective. He wanted to
be a composer. He didn't want to just write words
for Bernstein's music. He felt like it was stepping
backward, like he was failing. So he goes to
his mentor, Oscar Hammerstein, for advice. And
Oscar, being the ultimate pragmatist, said, take
the job. You'll work with professionals at the
top of their game. It's a foot in the door. You'll
learn how the big boys do it. So he takes it.
And he writes some of the most famous lyrics
in the history of theater. Maria, tonight, America,
somewhere. But there's a bitter aftertaste here
regarding the credit and the money, isn't there?
A very bitter one. Originally, the billing was
supposed to be lyrics by Leonard Bernstein and
Stephen Sondheim. But as they worked. Bernstein
realized Sondheim was doing the heavy lifting
on the words. So Bernstein, very generously,
offered to take his name off the lyric credit
entirely. Which sounds like a good thing. Soul
credit. That's what he wanted. It is a good thing
for your ego. But then came the conversation
about the royalties. The original split was Bernstein
getting 3 % of the gross for the music and the
lyricist's credit getting 1%. Okay. When Bernstein
offered Sondheim soul credit, he also offered
to even out the lyricist's pot. He said, I'll
take 2 % for the music and you take 2 % for the
lyrics. And Sondheim said yes, obviously. He
said no. He was so desperate to be seen as the
sole lyricist to have that validation that he
refused the extra percentage point. Oh, that
hurts. Think of the West Side Story royalties
over 70 years. That is a fortune. We're talking
millions and millions of dollars. He later said
he wished someone had stuffed a handkerchief
in his mouth and just forced him to take the
money. But it puts him on the map. He's the hot
new lyricist in town. So now finally he can write
his own music, right? The trap has sprung. You
would think. But then comes 1959. The project
is gypsy. Maybe the greatest American musical
ever written. That Overture. It's just a killer.
So Sondheim is asked to write the show. He agrees,
assuming he's the composer -lyricist. But the
star is Ethel Merman. The voice of Broadway.
The biggest diva in the business. A living legend.
And she was not about to take a risk on an unknown
kid writing her songs. She had just come off
a flop, and she needed a guaranteed hit. She
demanded a veteran composer, Jules Stein. So
Sondheim is shoved back into the box, just lyrics.
Again. He was crushed. He almost turned it down.
And once again, he went to Hammerstein, who told
him, take the job. Think what you'll learn writing
for a star of that magnitude. So he does it.
And the lyrics are incredible. I mean, Rose's
turn at the end of the show isn't just a song.
It's a nervous breakdown set to music. It is
a complete psychological unraveling. But you
can feel the pressure building in him. He finally
breaks out in 1962 with A Funny Thing Happened
on the Way to the Forum. His first Broadway hit.
with both music and lyrics by him. And it remains
the longest running show he ever wrote. It's
a huge old -fashioned hit. But interestingly,
he doesn't just keep writing comedies, he pivots.
And this brings us to the 1970s, the collaboration
with the director Hal Prince. This is where Sondheim
becomes a Sondheim. This is the golden era, the
high watermark. From 1970 to 1981, Sondheim and
Prince basically reinvented the genre with something
they called the concept musical. Right. So let's
define that for the listener. We hear that term
a lot. What is the difference between a traditional
musical and a concept musical? A traditional
musical think, The Sound of Music or My Fair
Lady, is driven by plot. It has a linear story,
a beginning, middle, and end. Events happen in
chronological order. Boy meets girl, boy loses
girl, boy gets girl back. Something like that.
A concept musical is organized around a theme
or an idea, not a plot. The timeline might be
fractured. The characters might be archetypes
representing different viewpoints. It's more
like a collage than a storybook. And the first
big shot in this revolution was Company in 1970.
Right. Company has no plot. It's a show about
a guy named Bobby on his 35th birthday, and we
just see a series of vignettes with his married
friends. That's it. The whole show is an exploration
of one theme, the difficulty of emotional connection
in a modern urban environment. It was sophisticated,
it was brittle, and it was incredibly adult.
It wasn't escapism. He was holding up a mirror
to the audience in New York and saying, Look
at your own neuroses. And the music matched that.
It was nervous. It had this pulsing, rhythmic,
urban energy. If you watch the documentary, original
cast album, Company, which is a must watch for
anyone interested in this. Oh, it's incredible.
You see the intensity. There's that famous scene
of Elaine Stritch trying to record the ladies
who lunch at four in the morning. She's exhausted.
She's screaming. Sondheim is in the booth looking
hypercritical. It wasn't just let's put on a
show. It was high stakes art. So after Company,
they pivot to Follies in 19... Which is, it's
basically a ghost story. It's a reunion of old
showgirls in a crumbling theater that's about
to be torn down. And as they're there, the ghosts
of their younger selves appear on stage with
them. And Sondheim did something brilliant with
the music here. He wrote pastiche songs. Yes.
For the flashback sequences, he wrote songs that
sounded like they were written by old 1920s and
30s composers like Gershwin or Cole Porter. They
were brilliant imitations. But then the characters'
reality, their present -day misery, is represented
by these dissonant, angry, complex, modern songs.
The whole show is about the clash between your
golden memories and your gray reality. A masterpiece,
but a huge money loser. Then, Little Night Music
in 1973, which feels like a total left turn.
It's romantic, it's lush, it's beautiful. It
is, but it's a Sondheim romance, which means
it's still about regret and missed chances. But
he set a very specific constraint for himself
on this one. Right, the waltzes. The entire score
is written in 34 variations of it. waltz time
why limit yourself like that why all waltzes
because 34 time is inherently unstable one two
three one two three it's always spinning it never
settles down like a solid 44 march it perfectly
captures the feeling of the characters in the
show who are constantly falling in and out of
love changing partners spinning out of control
at a weekend party in the country and of course
it gave him his only true pop hit the one song
everyone knows Send in the Clowns. Which is,
ironically, a very simple song musically. But
it's structurally perfect. Frank Sinatra covered
it. Judy Collins. It became this massive standard.
It proved that Sondheim could write a melody
the whole world could hum. He usually chose not
to. Because the characters and situations were
more complicated than that. Exactly. Which brings
us to... The complicated one. Sweeney Todd. The
Demon Barber of Fleet Street, 1979. A musical
about a barber who kills his customers and his
landlady bakes them into pies. It sounds like
a bad joke or a B -movie, but they treated it
like an opera. This is where God is in the Details
really shines. The score is almost entirely music.
It's terrifying and hilarious at the same time.
The song A Little Priest at the end of Act One
is my favorite example of this. It's a jaunty
waltz, and they are literally discussing which
professions would make the best tasting pies.
It's a pun -filled masterpiece of black comedy.
They are deciding which professionals taste best.
The shepherd's pie peppered with actual shepherds,
or the politician is so oily it needs to be served
with lettuce. It's a masterclass in wordplay,
but underneath all the jokes, there is this boiling
rage against the class system. It's grand guignol,
high horror, and high comedy blended together.
But this incredible winning streak had to end.
And it ended with a crash in 1981. Marilee, we
roll along. Ah, yes. This is the great heartbreak
of his career. The concept was brilliant. It's
a story told backwards. So you start at the end
and end at the beginning. Right. You start with
the characters as cynical middle -aged sellouts.
And the show moves back in time until the final
scene where they are young, idealistic dreamers
on a rooftop ready to change the world. Why didn't
it work? The audience couldn't follow it. They
saw the main character, Franklin Shepard, as
a complete jerk in the first scene. So they didn't
care about him for the rest of the show, even
as he got younger and more innocent. Also, the
casting was. an issue a huge issue they cast
actual teenagers to play the parts who then had
to age down it just didn't land the show opened
to brutal reviews and closed in less than two
weeks Sondheim was devastated. He felt betrayed
by the critics and the community. He actually
considered quitting, didn't he? The notes mentioned
he wanted to write video games. He was serious.
He was a huge gamer and puzzle fan. He thought
about designing video games or writing murder
mysteries. He wanted to leave the theater behind
because he felt the theater had rejected him.
And it also ended his regular collaboration with
Hal Prince. But then, a few years later, he sees
a play off -Broadway by a guy named James Lapine.
And this starts the second great era of his career,
the Lapine era. And this is where things get
really artsy. Hal Prince was a showman. He loved
glitz and big theatrical staging. Lapine was
a visual artist, a photographer. He was quiet,
more intellectual. He brought a totally different
energy to the table. And their first collaboration
is, in my opinion, his absolute masterpiece,
Sunday in the Park with George. 1984. A musical
about the pointillist painter Georges Seurat
creating his famous masterpiece, A Sunday Afternoon
on the Island of Legrand Shot. And here is where
we see that principle we mentioned earlier, content
dictates form. Seurat painted with pointillism,
tiny dots of color that blend in your eye. How
did Sondheim translate that into music? He wrote
pointillist music. He used staccato notes, like
little dots of sound. Ping, ping, ping. The piano
mimics the brush strokes. He used these repetitive
hypnotic motifs that eventually coalesce and
build into a big, sweeping, gorgeous melody.
It's incredibly difficult to sing, but the effect
is that you are literally hearing the painting
being created. It won the Pulitzer Prize for
drama, and he gave us the song Finishing the
Hat, which is basically the anthem for anyone
who has ever... tried to make something. Oh,
absolutely. It perfectly captures the isolation
and the obsession of the artist. The idea that
while everyone else is out living life, going
to picnics and parties, you are in the studio
obsessing over a tiny detail. Look, I made a
hat where there never was a hat. It's Sondheim's
autobiography in a song. Then they did Into the
Woods in 1987, which takes all these classic
fairy tales and asks what happens after Happily
Ever After. This is probably his most performed
show today. It's accessible, but it's also incredibly
deep and dark. And there's a fun debate about
this show regarding The Witch's opening number.
It's very fast, very rhythmic spoken word. A
lot of people claim it's the first rap song on
Broadway. It certainly sounds like it. Greens,
greens, nothing but greens. Yeah. Beans, beans,
and nothing but beans. It flows like rap, for
sure. But Sondheim, being the musical historian
he was, actually pushed back on that claim. He
credited The Music Man, specifically the opening
number Rock Island with the salesman on the train,
as the first real proto -rap. But The Witch certainly
brought that rhythmic intensity to a modern audience.
Their final major collaboration was Passion in
1994, which is... It's a tough watch. It is a
very tough watch. It's about a sick, unattractive
woman who relentlessly, obsessively stalks a
handsome soldier until he eventually loves her
back. It's uncomfortable. It challenges your
entire idea of what love is. Is it romantic?
Or is it a sickness? It won the Tony for Best
Musical, but it was the shortest running show
to ever do so. Which I think proves that Sondheim
was never going to just give the audience what
they wanted. He gave them what he was interested
in exploring, no matter how difficult. Let's
pivot to his late career. He didn't slow down
on the risk -taking. We have to talk about assassins.
1990, off -Broadway. A musical review where the
main characters are everyone who tried to kill,
successfully or not, the President of the United
States. John Wilkes Booth, Lee Harvey Oswald,
Squeaky Fermé, John Hinckley. Who thinks, hey,
that sings? Sondheim did. And he considered it
one of his most perfect works. He argued that
it's about the dark side of the American dream.
The Constitution says we have the right to the
pursuit of happiness. These assassins are all
people who felt cheated out of their happiness
and decided to take it out on the ultimate symbol
of the country. It's terrifyingly relevant. And
he kept working right up to the end. He had a
show that went through a million titles, Wise
Guys Bounce, finally Roadshow. And his final
show, here we are. based on Luis Buñuel films,
premiered posthumously in 2023. He died with
his boots on, essentially. Still writing, still
creating. We've talked a lot about the work,
but I want to go back to the mind we mentioned
in the intro, the puzzle master. This wasn't
just a metaphor for him. He literally introduced
cryptic crosswords to America. He did. In the
late 60s, he created these incredibly complex
cryptic crosswords for New York Magazine. He
was obsessed with games. His house in Turtle
Bay was filled with antique board games, coin
-operated machines, puzzles. And skeletons, apparently.
It sounds like a haunted funhouse. Yeah. But
it was a sanctuary for his mind. He even co -wrote
a movie called The Last of Sheila with Anthony
Perkins. You know, Norman Bates from Seiko. I've
seen that movie. It is so intricate. It's a hoodoonit
where the clues are all based... on wordplay
and games. Exactly. And the main character in
the famous stage play Sleuth, the obsessively
game -playing mystery writer, is partially based
on Sondheim's real -life reputation. He was always
looking for the solution, for the perfect construction.
I wonder if that's why his lyrics feel so inevitable.
He treated a rhyme scheme like a crossword puzzle.
It had to fit perfectly. No cheating. Absolutely.
He had a rule. True rhyme only. No near rhymes
or slant rhymes like home and alone. It had to
click into place like a lock. He believed that
perfect rhymes make the audience subconsciously
trust the intelligence of the character who's
singing. Let's talk about his legacy as a teacher.
Because Oscar Hammerstein taught him and he took
that idea of paying it forward very, very seriously.
He viewed it as a moral obligation. He said it
was about passing on what Oscar passed on to
me. And the list of people he mentored is incredible.
Most famously, Jonathan Larson, who wrote Rent.
There's that scene in the movie Tick, Tick, Boom,
where Andrew Garfield, as Larson, gets a voicemail
from Sondheim. A lovely meta detail about that.
Sondheim actually rewrote that voicemail for
the movie and then voiced it himself. He told
the filmmakers, I wouldn't say it like that.
He wanted it to be accurate to how he would actually
encourage a young artist. He was very gentle
and supportive with Larson. He was also deeply
involved with Lin -Manuel Miranda. He was. When
Miranda was writing Hamilton, he showed early
drafts to Sondheim. Sondheim was actually skeptical
at first. He worried that a whole evening of
rap music might get monotonous. But once he heard
the complexity of the rhymes, he was completely
won over. He respected the craft. He didn't care
about the genre. He cared about the execution.
I also love this story about Adam Gettle, who's
Richard Rodgers' grandson. It shows Sondheim's
tough love side. Yes, yes. Adam Gettle, a brilliant
composer in his own right, showed Sondheim some
of his early work, probably expecting a pat on
the back, and Sondheim just gave him brutal...
detailed page -by -page notes, Gettle was crushed.
And Sondheim later apologized to him and said,
I was trying to be constructive, not encouraging.
That is a crucial distinction. It is. He treated
these young writers as peers, not children. He
respected them enough to tell them the truth,
just like Hammerstein did for him. Before we
wrap up, I wanted to distill his philosophy.
He had four core principles he wrote about in
his lyric collection, Finishing the Hat. What
were they? They are the four commandments of
Sondheim. Number one, content dictates form.
The way something is said should be inseparable
from what is being said. The music must sound
like the subject. Pointillism for a pointillist
painting. Exactly. Number two, less is more.
Don't overwrite, don't over -explain. Number
three, God is in the details. That one feels
like the one to tattoo on your arm. It's the
truest one for him. Whether it's the specific
interval in a melody or the specific button on
a character's costume, that's where the art lives.
And number four, clarity. Above all, be clear.
And finally, the man himself. We described him
as isolated as a child. Did that ever really
go away? He often described himself as an outsider,
someone people wanted to kiss and kill. He didn't
come out as gay publicly until he was 40. He
didn't live with a partner until he was 61 when
he met Peter Jones. He married his husband, Jeffrey
Romley, in 2017. But there was always a sense
of solitude about him. And he hated being pigeonholed.
He rejected the idea that his songs were gay
anthems, right? He did. People often cite somewhere
from West Side Story, there's a place for us
as a gay anthem. And Sondheim said, look, if
that's a gay song, then all songs about getting
away from the realities of life are gay songs.
He wanted his work to be universal. Not specific
to one identity. He didn't want to be the gay
composer. He just wanted to be a great composer.
So what is the takeaway for us? Why does Sondheim
matter to someone who maybe doesn't even like
musicals? Because he fundamentally changed the
way we tell stories with music. He proved that
you can be entertaining and intellectual at the
same time. You don't have to dumb things down
to reach an audience. You can ask them to work
a little bit, to lean in. And that brings me
to my final thought. Sondheim once said he preferred
theater. to concert music because he wanted communication
with audiences. He wanted to make them feel something.
But he was also this man of math, of puzzles,
of intellectual detachment. It's the central
paradox of his life and work, the cold intellect
and the warm beating heart. Right. So here's
the question for you to think about. Does that
God is in the details approach, that relentless
complexity and precision, does that create a
barrier between the art and the audience? Or
is that specific, intricate complexity exactly
what makes the connection so human and so enduring?
Maybe by being so hyper -specific, so detailed,
he actually became universal. Because life is
detailed. Life is a puzzle. And we see ourselves
in the attempt to solve it. I think that's it.
We recognize the messiness and the intricacy
of our own lives in the complex structures he
built on stage. And the fact that we are still
listening, still analyzing and still crying at
his shows 50 years later, I think that proves
the connection is very, very real. I think so,
too. That's it for this deep dive into Stephen
Sondheim. Thanks for listening. See you next
time.