Okay, let's get into it. Today we are doing a
deep dive into one of the, I mean, just one of
the most glittering but ultimately tragic figures
in all of American literature, Francis Scott
Key Fitzgerald. That's right. He was the voice,
really the definitive voice of the roaring 20s.
A man who absolutely lived the high life he wrote
about only to, well, to watch it all crumble.
His own spectacular personal and professional
decline happening in real time. And that arc,
you know, that glittering rise, the brutal fall,
and then this posthumous canonization, that's
what makes Fitzgerald such a perpetually fascinating
figure for you to study. So that's our mission
for this deep dive. Exactly. To really pull apart
and extract the most important insights about
his dual identity. And that identity is just
split right down the middle, isn't it? Completely.
On one hand, he's the ultimate chronicler of
the jazz age. He basically defined that entire,
you know, morally permissive era for the rest
of the country. But on the other side, he was
a really serious modernist writer who just failed
commercially. Financially, he failed during his
lifetime, dying, believing his life and his work
were in his eyes. Total failures. It's the American
myth of success and failure just distilled into
one man. Yeah. And when you look at the sheer
output, it's just extraordinary, especially for
a relatively short life. It's a huge body of
work. Huge. He published four completed novels,
one tragically unfinished one, The Last Tycoon,
four story collections, and a staggering 164
short stories. Wow. That volume alone, it tells
you about an immense drive, but also, as we're
going to see, it points to a tremendous, almost
crippling financial necessity. I think that's
the thing that's so fascinating here and what
we really need to wrestle with right away is
that central paradox of his career. Fitzgerald
achieved this, you know, transcendent success.
He was a celebrity author in the 1920s. He made
a fortune. But he absolutely did not get the
critical or financial acclaim that was really
commensurate with his talent. Not until decades
after he died in 1940. That reversal of fortune
is almost unprecedented in American literature.
He died poor, thinking he was irrelevant. And
yet now he is, without question, regarded as
one of the greatest American writers of the 20th
century. Required reading. His books are taught
all over the world. Globally, yeah. And he didn't
just write about the Jazz Age. He kind of, he
named it. He literally named it. He popularized
the term in his short story collection, Tales
of the Jazz Age. So he was both the product and
the narrator of that specific chaotic time. Which
makes me wonder, though, was the Jazz Age truly
this era of disillusionment? Or was it maybe
just the invention of a few high profile writers
like Fitzgerald who then, you know, profited
from romanticizing their own bad behavior? That's
a critical question. Yeah. And it speaks directly
to the the inherent contradiction in his person.
and his writing style, his friend, the great
literary critic Edmund Wilson, he gave one of
the best syntheses of Fitzgerald's unique voice.
Okay, what did he say? Wilson really captured
this war between the man and his material. He
noted that Fitzgerald was romantic, but also
cynical. He was bitter, yet ecstatic. Astringent,
but also incredibly lyrical. That sounds like
Wilson was maybe being a little generous. I mean,
overlooking Fitzgerald's self -destructive vanity
by just calling it an Irish gift. Well, perhaps.
But Wilson went on to praise his ability to turn
language into something. And this is the quote,
iridescent. And surprising. Iridescent and surprising.
I like that. It implies a writer who had this
innate, almost magical ability with words, yet
was constantly dragging himself through the mud
of his own anxieties and his own excesses. Yeah,
you can see why his writing always feels so urgent
and just deeply conflicted. It's incredible that
this lyrical voice, so capable of such a clear
-eyed social critique, came from someone so cynical
and, frankly, so self -absorbed. So let's trace
that cynicism back. Let's go to the source. His
childhood. Fitzgerald was the permanent outsider,
and that started very early. You have to begin
there. With his relatively humble beginnings
in St. Paul, Minnesota, he was born into a middle
-class Catholic family in 1896. And he was named
after his famous distant cousin, Francis Scott
Key. The man who wrote the Star -Spangled Banner.
So you have this profound connection to the national
identity baked right into his name. But the family's
financial reality was much less grand. The family
history here is like a microcosm of the American
promise and its failure, which became his life's
theme. It really is. His mother, Mary McQuillan
Fitzgerald, came from an Irish immigrant family
that got rich as wholesale grocers. So she has
some security. But his father, Edward, he ran
a wicker furniture business that failed just
a year after Scott was born. That failure is
key. It forced the family to move to Buffalo,
New York, and Edward worked for Procter & Gamble
until he was fired in 1908. Fired? Fired. And
the records we have show his father really struggled
with destitution and alcoholism after that. So
you've got young Scott growing up with this deep
internal conflict. His mother's inheritance lets
them keep up this comfortable middle -class lifestyle.
He has the appearance of wealth, access to good
schools. Right, the veneer. But just beneath
that veneer is the constant, gnawing instability
of his father's failure. He was always striving
to meet the standard of the genuinely wealthy
people around him, but he never had the old money
or the true status to compete. That was his formative
anxiety. He later admitted this was the absolute
key to his sensibility. He knew what wealth looked
like. He could mimic it perfectly. But he understood
the desperation of not belonging. Which made
him the perfect observer of the wealthy. The
perfect observer. Yeah. Because he envied and
resented them in equal measure. And this is where
his family history gets really interesting. There's
this footnote that sounds like something he would
have made up for a story. It really does. Yeah.
His father's first cousin, twice removed. was
mary surratt who was hanged in 1865 for conspiring
to assassinate abraham lincoln it's an incredibly
potent deep american lineage it encapsulates
both national triumph and national tragedy you
have the guy who wrote the national anthem on
one side and on the other a figure associated
with the profound irreparable break of the civil
war and the assassination of its great leader
this duality, the soaring ideal of America and
its dark, hidden failures. It feels like it subconsciously
predisposed Fitzgerald to his central themes.
The decay hidden beneath glittering surfaces.
Exactly. It suggests the seeds of that cynicism
were there right from the beginning. The real
literary seed, though, that got planted when
he attended the Newman School in New Jersey.
Yes, that's where he met Father Sigourney Fay.
He became a crucial early mentor. Fay was this
accomplished, well -read figure who saw Scott's
talent very early on and really encouraged his
literary ambitions. And that encouragement carries
him right into Princeton University. Where he
enrolled as one of the only Catholics in the
student body, which, again, instantly cemented
his status as an outsider looking in. But he
thrived there intellectually. He jumped right
into the campus literary scene, writing for the
Princeton Triangle Club, the Princeton Tiger,
the Nassau Lit. And this is where he forges the
relationships that will define his entire professional
life. He befriends two key people, John Peel
Bishop, who became an important modernist poet,
and the great literary critic, Edmund Wilson.
Wilson, who would later be the one to champion
him after his death. But the defining personal
drama, the one that really launched the rocket
of his career, that began during Christmas break
of his sophomore year. Right. He was 18. He meets
Ginevra King. A 16 -year -old Chicago debutante.
She was the original muse, the lightning strike.
She represented everything he desired and everything
he could not have. And this is where that crucial
class barrier narrative just slams right into
his life. It really does. Ginevra was fabulously
wealthy, upper class, privileged, the ultimate
golden girl of the Midwest. Her family, especially
her father, just saw Fitzgerald as a completely
unsuitable social climber. And her father's words
to him, or at least the ones that have been passed
down, they became this line that just haunts
American literature. It's the ultimate articulation
of Fitzgerald's deepest anxiety. Poor boys shouldn't
think of marrying rich girls. It's so brutal
in its simplicity, but it also perfectly crystallizes
this rigid class system in America that Fitzgerald
spent his entire career trying to dissect. That
phrase, whether it was spoken exactly like that
or just internalized through a thousand social
slights, it became the absolute central recurring
theme of his entire body of work. The unfairness
of it all. The unfairness. This idea that a poor
young man, intelligent and ambitious, can't transcend
his status purely because of a lack of generational
wealth. And the literary result is just undeniable.
Ginevra, the girl who got away because of class,
she becomes the model for Isabelle Bourget in
this side of paradise. And most famously. Daisy
Buchanan. The elusive, wealthy, and ultimately
careless Daisy Buchanan in The Great Gatsby.
The rejection was emotionally catastrophic for
him. We know how profound it felt because a suicidal
Fitzgerald get enlisted in the U .S. Army during
World War One. And he was specifically hoping
to die in combat. This wasn't just patriotic
service. No, this was a desperate, self -destructive
reaction to the pain of social rejection. And
he was stationed at Fort Leavenworth, where he
served remarkably under Captain Dwight D. Eisenhower.
A fascinating little historical detail. The future
literary giant. just chafing under the authority
of the future president and supreme allied commander.
And he did not like him. The sources say he intensely
disliked Eisenhower, found him stiff, authoritative.
So while he was waiting to be deployed, fearing
he would die in Europe, he hastily wrote this
massive 120 ,000 -word manuscript. The romantic
egotist. In just three months, he was desperate
to publish a novel to leave some artifact of
his existence before he died in battle. Scribner's
thankfully rejected it. But the editor, the great
Max Perkins, was impressed. He wisely praised
the writing and encouraged him to revise it.
So Fitzgerald didn't die on the Western Front.
But he did meet his next great muse, who would
demand a very different kind of sacrifice. And
that, of course, was Zilda Sayre. In 1918, while
he was garrisoned near Montgomery, Alabama, he
met the 17 -year -old Southern Belle. And if
Ginevra was that polished, old -money ideal,
Zelda was the dazzling, reckless embodiment of
the modern American spirit. She was part of Montgomery's
exclusive country club set, and her family owned
the first White House of the Confederacy. So
she's linked to this deep south, complicated,
aristocratic past. And just like Ginevra, Zelda
initially rejected his marriage proposal. But
this rejection, unlike the first one, was based
purely on hard numbers. His lack of financial
prospects. Exactly. His Catholic background was
a concern for her Episcopalian family, but money
was the clear primary barrier. And this second
rejection was pivotal. It drove him out of the
army to New York City and forced him to chase
success, not as an artistic fulfillment, but
as a financial imperative. He had to prove he
could afford the life Zelda had always known.
And he struggled. Profoundly. He failed spectacularly
to get a newspaper job and ended up writing advertising
copy, living in this cramped single room on the
west side. This is where we get that great little
historical detail of his most famous piece of
ad copy. Created for an Iowa laundry. We keep
you clean and muscatine. It's just a perfect
illustration of the contrast between the soaring
ambition of the Princeton literary star and the
mundane reality of a struggling ad man. And the
volume of failure before the breakthrough is
just astonishing. He was rejected over 120 times
for his stories. 120 times. And sold only one
Babes in the Woods for a pittance of $30. He
was living in relative poverty, writing about
a world he desperately wanted to join but just
couldn't afford. The difficulty of breaking in,
despite his obvious talent, it really speaks
to the sheer tenacity that you need to succeed.
And the financial pressure? It finally led to
the second breaking point. Zelda finally broke
off the engagement in June of 1919. And this
rejection, coming after Ginevra, was just catastrophic.
He threatened to jump from a window ledge, carried
a revolver, contemplated suicide. It was total
rock bottom. So defeated and rudderless, he quits
advertising, moves back to his parents' home
in St. Paul, and he stakes everything on one
last desperate attempt to become a successful
novelist. And this wasn't just an artistic choice.
This was... Survival. It was. He abstained from
alcohol, from parties, living like a monk, and
just aggressively revised the romantic egotist
into this side of paradise. And that desperation,
it fueled the lightning strike. Published on
March 26, 1920, the novel, which was basically
about his Princeton years and his romances with
Ginevra and Zelda, became an instant cultural
sensation. It sold 40 ,000 copies in the first
year alone. It cemented his reputation overnight.
Critics like H .L. Mencken called it the best
American novel of the year. Columnists saw it
as the first realistic American college novel,
something that actually captured the cynical,
fast -moving spirit of the postwar youth. And
his paychecks reflected that. He went from making
$30 a story to magazine rates of $1 ,000 almost
instantly. And this fame, this financial success,
it immediately brought Zelda back. She resumed
the engagement because he could now afford the
affluent lifestyle she was accustomed to. But
this is a critical point that foreshadows their
entire tragedy. Fitzgerald married her even though
his feelings were at an all -time low. He told
a friend, I wouldn't care if she died, but I
couldn't stand to have anybody else marry her.
Wow. It's a chilling line. They married on April
3, 1920, and Fitzgerald later claimed neither
of them still loved the other. So the marriage
was based not on love, but on financial security
and social validation. This is where the definition
of the jazz age celebrity really begins. They
moved into the Biltmore Hotel in New York and
instantly became known for their just juvenile,
outrageous behavior. We have these wonderful,
unbelievable anecdotes. Scott doing handstands
in the lobby, Zelda sliding down the banisters.
Behavior that got them asked to leave. So they
moved to the Commodore Hotel and famously spent
half an hour just spinning in the revolving door,
completely drunk. Dorothy Parker recalled seeing
them riding on the roof of a taxi. She said they
looked as though they had just stepped out of
the sun. Everyone wanted to meet them. They were
the living, breathing epitome of this new cultural
moment. And Fitzgerald became the flag bearer
for this youth and revolt. He helped define the
Jazz Age as this morally permissive era. a disillusionment
with old social norms, and an obsession with
self -gratification. He described it as a race
along under its own power, served by great filling
stations full of money. And that whole hedonistic
lifestyle was just relentlessly fueled by alcohol.
Those gin and fruit concoctions that let them
maintain that ecstatic public facade. But while
it looked glamorous privately, it led to bitter
quarrels, deep jealousies, and constant accusations
of infidelity. Confirming to both of them, probably,
that their marriage was fundamentally doomed.
In 1921, their daughter, Frances Scotty Fitzgerald,
was born. And this brings us to another famous,
darkly insightful anecdote that immediately found
its way into his fiction. Right. As Zelda was
coming out of the anesthesia after childbirth,
she had this famous rambling remark. I hope it's
beautiful and a fool. A beautiful little fool.
And Fitzgerald used that line almost verbatim
for Daisy Buchanan's dialogue in The Great Gatsby.
It just shows how closely he mined their turbulent,
chaotic, private life for his fiction right from
the very start. Everything was material, even
his wife's semi -conscious words after delivering
their child. Let's move now into the period that
gave us his greatest work. His second novel,
The Beautiful and Damned, in 1922, that propelled
him even farther into the cultural elite. It
sold 50 ,000 copies. And this book was even more
explicitly modeled on their marriage. Anthony
Patch was a version of Scott, and Gloria Patch
represented what he saw as Zelda's chill -mindedness
and selfishness. But the problem was, the financial
pressure, it didn't go away. It got worse. He
tried to maintain the success with a play, The
Vegetable, in 1923, but it was an unmitigated
disaster. A disaster the audience literally walked
out during the second act. So this flop was a
crucial financial pivot point for him. He's mired
in crushing debt from the play's failure, and
he's forced into a pattern he deeply resented.
Writing short stories just to restore his finances.
This is the famous whoring of his talent. He
saw most of these commercial stories as worthless,
but he had to churn them out for the high rates
paid by magazines like the Saturday Evening Post.
He called it rotten stuff, but the money was
necessary to pay the bills and keep Zelda happy.
The one significant exception he noted was Winter
Dreams, which he explicitly said was his first
attempt at the Gatsby idea. So while he was trying
to make money in Great Neck, Long Island to be
near Broadway, he's exposed to this incredible
extravagance of the neighboring mansions, which
would, of course, define the setting of his third
novel. Critically, he encountered a real -life
figure who provided the blueprint for Jay Gatsby,
his wealthy neighbor, Max Gerlach. And here's
where the legend of Gatsby just meets reality.
Gerlach was a fascinating figure, a gentleman
bootlegger, a former WWI major. who flaunted
his nouveau riche status by throwing these unbelievably
lavish parties. He never wore the same shirt
twice and regularly used the phrase old sport
to address everyone he met. He was the guy. He
was the guy. He fostered myths about himself,
that he was related to the German Kaiser. He
was the embodiment of that mysterious self -made
man who had achieved financial success but lacked
the social history to back it up. He was the
perfect template for Jay Gatsby. So in May 1924,
Fitzgerald moves the family to the French Riviera
to work on this new novel. He's determined to
make it a conscious artistic achievement, deliberately
shifting away from the autobiographical realism
of his first two books. But the personal chaos,
it followed them. While they were abroad, a major
marital crisis developed that caused a permanent
irreparable breach. Zelda became infatuated with
a French naval aviator, Edward Jazon, and she
asked for a divorce. And Fitzgerald, in this
desperate, panicked reaction, he locked her in
the house. Wow. Jazon left, apparently having
had no intention of marrying Zelda, but the humiliation
and the breach of trust were permanent. Zelda
then overdosed on sleeping pills. They eventually
smoothed it over publicly, but they never truly
discussed it. They just let the damage fester.
And The Great Gatsby was published shortly after
that on April 10th, 1925. And despite being lauded
by literary giants like T .S. Eliot, who praised
its control and narrative mastery. Eliot loved
it, right? He called it a huge step forward.
A huge step, exactly. And Willa Cather, Edith
Wharton, they all saw it as a massive leap forward.
But commercially. It was a total flop. A complete
dud. I mean, it sold fewer than 23 ,000 copies
in the first year. That's nothing compared to
his other books. Nothing. And get this. His domestic
royalties in 1929, so four years later, amounted
to, what was it, $5 .10. Wow. Just wow. Five
dollars. So you realize the man who wrote the
great American novel made less than six dollars
from it four years after it came out. That financial
anxiety must have just been a constant suffocating
cloud over his art. The time in France also coincided
with the rise of the lost generation. Fitzgerald
befriended the American expatriate community
in Paris, including Gertrude Stein, James Joyce,
and most importantly, Ernest Hemingway. He really
admired Hemingway, saw him as a kind of literary
conscience. He did. But their friendship is one
of the most fraught in literary history. Constantly
strained, often poisonous, and largely because
of Zelda. The infamous Hemingway -Zelda conflict.
Right. Hemingway outright disliked Zelda. He
called her insane and an evil shadow in his memoir,
A Movable Feast. And he believed she was the
one corrupting Scott's talent. He fundamentally
believed that. He argued she pressured Scott
to write the lucrative short stories instead
of focusing on novels just to maintain their
extravagant lifestyle. This necessity, Hemingway
argued, was whoring his talent. And Zelda didn't
help her own case, did she? She confirmed her
commercial preference, saying she always felt
a story in the Saturday Evening Post was tops.
Because of the high pay and the wide readership,
it was a cultural divide. The perceived purity
of the novel versus the lucrative commercialism
of the mass market short story. And the conflict
got intensely personal. And cruel. Very cruel.
Hemingway detailed how Zelda used homophobic
slurs, accusing Fitzgerald of having a homosexual
relationship with him, a claim Fitzgerald denied,
but which clearly shook him. It raises this important
question about his dynamic. If he was so desperate
for external validation, from Ginevra, from Zelda,
from Hemingway, that he felt he needed to prove
his masculinity. Right. He even had sex with
a prostitute to prove his heterosexuality. But
Zelda found the condoms beforehand, which just
sparked another bitter, jealous quarrel. The
sheer drama surrounding them was constant. It
was almost designed for public consumption, but
so deeply destructive privately. The incident
where Zelda threw herself down a flight of marble
stairs because Fitzgerald was engrossed in a
conversation with Isadora Duncan and ignored
her. It's just a perfect illustration of her
escalating desperate attempts to control all
the attention. The return to America didn't stabilize
anything. Their marriage was a wreck. The need
for money was ever more pressing and it forced
him into a truly unhappy professional detour.
Hollywood. In 1927, he accepts a screenwriting
invitation. a massive financial commitment that
he needed to pay off debts. But the novelty faded
fast. They were known for these wild, juvenile
pranks. Like boiling expensive watches in a pot
of tomato sauce, which just outraged their new,
staid Hollywood acquaintances. And Fitzgerald,
desperately seeking some kind of intellectual
connection, found a new muse in the 17 -year
-old starlet Lois Moran. He was captivated by
her youth and her admiration for him. She inspired
the character Rosemary Hoyt in Tender is the
Night, the beautiful, fresh young actress. He
also wrote her into the short story Magnetism.
This pattern of finding muses and immediately
mining their lives for fiction was just a constant
in his career. And naturally, Zelda's jealousy
manifested violently. She set fire to her own
expensive clothes in a bathtub as a self -destructive
act, and she disparaged Moran as a breakfast
food. After only two months in Hollywood, the
unhappy couple left. And this period really marks
the start of the final devastating descent, primarily
because of Zelda's escalating mental health crisis.
By 1930, her behavior became truly violent and
erratic. The incident along the Grand Corniche
in France. That's just terrifying. Where she
seized the car's steering wheel in an attempt
to drive herself, Scott, and their daughter over
a cliff. That was the ultimate sign of collapse.
It's absolutely horrifying. Scene of domestic
terror that must have haunted him. And following
this, in June 1930, doctors finally diagnosed
her with schizophrenia. She spent the rest of
her life in and out of expensive psychiatric
treatment. First in Switzerland, and later at
the Phipps Clinic at Johns Hopkins. H .L. Mencken
noted privately that Zelda was only half sane.
He expressed deep regret that Fitzgerald couldn't
focus on writing great novels because he was
forced to churn out magazine stories just to
pay for her extremely expensive psychiatric care.
It truly highlights the terrible cost of that
required affluent lifestyle. And here's where
the literary theft and conflict really peaked.
Fitzgerald was working on his fourth novel, which
drew heavily on the disintegration of their marriage.
The story of a promising young man marrying a
mentally ill woman. The very material of their
lives. And Zelda preempted him. She did. While
she was hospitalized, she wrote and sent her
own fictionalized account, Save Me the Waltz,
to Scribner's. Fitzgerald was furious. He saw
as a theft of his novel's plot material. He privately
called her a plagiarist and a third -rate writer.
It wasn't just personal, it was professional.
She had staked a claim on his artistic material.
Yet despite his anger, he persuaded Maxwell Perkins
to publish her novel. It failed, both commercially
and critically. And Fitzgerald's own work, Tender
is the Night. finally came out in 1934, a nine
-year gap from Gatsby. It received mixed reviews,
partly because its complex structure confused
critics, but primarily because Depression -era
audiences just saw Fitzgerald as an irrelevant
symbol of jazz age excess. And this brings us
squarely into the Great Depression and the cruel
reality of his financial decline. His glamorous
material was suddenly completely out of step
with the national mood. As one journalist noted,
Americans could no longer afford champagne or
trips to Montparnasse. Fitzgerald's works were
deemed elitist and materialistic, and his popularity
just plummeted. The financial situation was dire
and humiliating. By 1936, his book Royalties
amounted to a pitiful $80. $80 for the year.
He was in constant crushing debt, relying on
loans from his agent, Harold Ober, and his editor,
Perkins, just to keep Zelda institutionalized
and his daughter in school. He eventually severed
ties with Ober, his most loyal agent, purely
out of shame. He believed the agent had lost
faith in him because of his deepening alcoholism
and unreliability. And his health was crumbling,
too. The heavy drinking led to serious physical
ailments. cardiomyopathy, coronary artery disease,
recurring tuberculosis. Between 1933 and 1937,
he was hospitalized eight times for alcoholism
alone. The public low point came in September
1936. A journalist, Michel Mock, publicly reported
on Fitzgerald's alcoholism and career failure
in a nationally syndicated article. And that
piece, exposing his private struggle to the nation,
it so deeply damaged Fitzgerald's reputation
that it prompted him to attempt suicide after
reading it. He later referred to this whole period
of decline in his short story, The Crackup. The
necessity to pay for Zelda's confinement drove
the final Hollywood act. In 1937, he accepted
a lucrative MGM contract, nearly $30 ,000 a year,
his highest salary ever. But the bulk of it was
immediately consumed by Zelda's medical bills
and Scotty's school expenses. It was the salary
of a major success paying for the fallout of
a major failure. This period offered a brief,
sad attempt to reclaim the past. In 1938, he
reunited with Ginevra King, the original muse.
He was hoping to keep the illusion perfect, as
he told his daughter. But his uncontrollable
alcoholism ruined the meaning, and a disappointed
Ginevra returned to Chicago. The past. could
not be resurrected his final companion was the
gossip columnist sheila graham and there's this
truly depressing moment when he tried to buy
her a set of his novels as a gift only to realize
the bookstores had stopped carrying his works
that moment the realization that he was largely
forgotten as an author must have been utterly
demoralizing His screenwriting output was minimal,
often uncredited. He only got sole credit for
Three Comrades in 1938, despite doing dialogue
polish for huge projects like Gone with the Wind.
Which he disparaged as an old wives tale. Of
course he did. Director Billy Wilder famously
summarized Fitzgerald's Hollywood foray. He said
it was like a great sculptor who was hired to
do a plumbing job. His talent was being wasted
and he knew it. He mocked himself in the Pat
Hobby stories, writing about the miserable life
of a Hollywood hack who couldn't keep a job.
And yet he used his spare time, despite his failing
health, to work on his final unfinished novel,
The Last Tycoon, based on the film executive
Irving Thalberg. And in a moment of profound
reflection, nearing the end, he wrote this regretful
letter to his daughter. about his one great triumph.
That quote, that focus on duty to art over duty
to lifestyle, it forces us to turn our attention
from the tragedy of the man to the triumph of
his artistry. Right. Let's look closely at the
literary evolution of his novels versus the commercial
demands of his short stories, because that is
the heart of his crackup. We see a clear, discernible
progression in his novels. His authorial voice
clearly matured with each successive work, despite
all the external chaos. This side of paradise,
while a sensation, was criticized by his friend
Edmund Wilson for its poor form and construction,
its reliance on textual fragments, letters, poetry.
It was experimental, but kind of a mess. And
Fitzgerald was acutely sensitive to that kind
of criticism. He read those reviews, and Beautiful
and Damned was a direct attempt to improve. it
showed superior form and construction and a move
toward an ironical pessimistic style He was consciously
learning the craft. But The Great Gatsby was
the masterpiece precisely because it was a conscious
artistic pivot. He intentionally departed from
the sprawling realism of his first two novels
to create a pure, controlled, creative work.
He refined his prose. He consciously emulated
the literary styles of Joseph Conrad and notably
Willa Cather. Her novel, A Lost Lady, influenced
him greatly. Because it also features a wealthy
married socialite who kind of symbolizes the
decay of the American dream. Exactly. He was
moving away from biography and toward myth. And
the literary world, they recognized it. With
Gatsby, critics acknowledged he had upgraded
from being a brilliant improvisateur to a conscientious
and painstaking artist. He was deliberately using
symbolic language and setting the green light,
the valley of ashes, to communicate these really
deep themes. Gertrude Stein, a notoriously tough
critic. She argued that Fitzgerald had surpassed
his contemporaries, including Hemingway. Really?
Yes, due to his masterful ability to write in
natural sentences. She called him a genius who
would be read when many of his well -known contemporaries
are forgotten. What's fascinating here is the
stark contrast with his short fiction. His novels
showed this artistic progression. His 164 short
stories overall showed the opposite. And again,
the reason is simple and heartbreaking. Money.
Money was the primary impetus. He lamented, I
have to write a lot of rotten stuff that bores
me and makes me depressed. He actively tailored
them to commercial tastes, often rewriting stories
to add these forced happy plot twists. The saccharine
denouement that the editors of slick magazines
demanded. And he was rewarded handsomely for
this self -betrayal, which is why he kept doing
it. He was earning up to $4 ,000 per story at
his peak. The equivalent of a major annual salary
today. Just for churning out 15 to 20 stories
a year for the Saturday Evening Post. This gave
him the high life, but it just drained his artistic
energy. It created what his friend John Dos Passos
called literary schizophrenia. The daily battle
of deciding whether to do good writing that satisfies
the conscience or cheap writing that satisfies
the pocketbook. He debased his undeniable gift
by transforming these complex tales into social
romances with inevitably happy endings for the
commercial market. Okay, so let's look at the
enduring thematic power that transcends the quality
gap between the two forms. First, the generational
zeitgeist. Right. Fitzgerald was the foremost
chronicler of the Jazz Age. He defined a generation
who were adolescents during World War I, largely
untouched by its horrors and dedicated to the
fear of poverty and the worship of success. And
as Stein suggested, his fiction didn't just record
this generation, it kind of created it in the
public's mind, giving them a self -consciousness.
He became the standard bearer for youth and revolt.
He ridiculed critics who denounced his use of
modern alien slang and his depictions of premarital
sex, arguing they wanted to retain outdated ideas
about society that just didn't exist anymore.
What's so critical and so deeply relevant for
you today is his continuous, deep -seated preoccupation
with wealth, class, and the American dream. This
theme is just deeply rooted in his lifelong status
as a poor boy in a rich town, a poor boy in a
rich boy's school, a poor boy in a rich man's
club at Princeton. He harbored, and this is his
phrase, the smoldering resentment of a peasant
towards the wealthy, and he channeled that right
into his art. His work satirized the leisure
class. People who take all of the privileges
of the European ruling class and assume none
of its responsibilities. Even H .L. Mencken,
who criticized him for focusing too much on the
wealthy, admitted that he came the closest to
capturing their idiotic pursuit of sensation,
their almost incredible stupidity and triviality,
their glittering swinishness. He nailed it. And
the Great Gatsby specifically, it dissects the
entrenched class disparities and it provides
this stunning critique of the American class
system. It argues for the limits of the lower
class to transcend their birth status. Right.
Even if poor Americans become rich, the nouveau
riche, like Gatsby, they remain inferior to those
with old money. Like the Buchanans. Gasti's immense
wealth couldn't buy him the social history of
the Buchanans. That sense of eternal, unbridgeable
distance. That no matter what you achieve, there's
always an inherent club you can't join. That
is the ultimate American story. That kind of
social anxiety and status conflict is just as
relevant now as it was then. And this ties directly
into the theme of... otherness and appropriation,
Fitzgerald constantly felt like a societal outsider,
a parvenu, and he used that feeling to fuel his
writing. And this sense of otherness defines
his greatest character. Jay Gatsby is fundamentally
defined by his otherness and his obscure origins.
Tom Buchanan belittles him as Mr. Nobody from
Nowhere. Exactly. His success is seen as a threat
precisely because he is an outsider who lacks
the coveted status of old stock Americans. Scholars
find the fiction so enduringly relevant today
because it captures this perennial American experience
of social anxiety, status conflict, and resentment
towards outsiders, immigrants, the nouveau riche
successful minorities. Before we wrap up the
artistry section, we have to talk about his appropriative
tendency. His habit of lifting material directly
from the lives of others, something he did constantly,
almost pathologically. It was part of his process.
He quoted verbatim entire letters from his mentor,
Father Sigourney Faye, in this side of paradise.
For the beautiful and damned, he inserted actual
sentences from Zelda's diary. Which prompted
her to jokingly note in a review that she recognized
parts of her old diary that mysteriously disappeared
after their marriage. He borrowed biographical
incidents from his friend for the rich boy. He
truly saw everything in his life and the lives
of those around him as material for his craft.
And the most striking instance is with Ginevra
King. She wrote him a story as a parting gift
about being trapped in a loveless marriage but
pining for a former lover who attained wealth.
And scholars note the plot similarities at the
core of The Great Gatsby. He literally took the
emotional narrative of his first great love and
built his masterpiece around it, justifying it
because, to him, it was his life, his experience
to use. So we have this flawed, contradictory
man, a plagiarist of his own life and others,
who died on December 21st, 1940 at age 44, believing
his life and work were total failures. He died
of a heart attack due to occlusive coronary arteriosclerosis.
And the immediate critical response was harsh
and dismissive. They saw him as a failed alcoholic
and a mere chronicler of the jazz age. His New
York Times obituary cemented his work forever
to an era when gin was the national drink and
sex the national obsession. And Dorothy Parker's
famous line, uttered at his sparsely attended
visitation, just encapsulated the tragedy. She
murmured, the poor son of a bitch. A line taken
directly from Al Eliza's observation at Gadsby's
own sparsely attended funeral in the novel. The
fiction had become prophetic of the author's
own fate. Even in death, the complications continued.
His lifelong status as an outsider. The Catholic
Church initially denied burial in the family
plot because he was a non -practicing Catholic.
Forcing him to be buried in Rockville Cemetery
until 1975, when his daughter successfully petitioned
to have his remains and Zelda's moved to the
Catholic St. Mary's Cemetery. But the critical
reevaluation started almost immediately, and
it was largely driven by the loyalty of his friends.
Within one year, Edmund Wilson published The
Unfinished The Last Tycoon, and he included the
great Gatsby in the edition, which sparked new
critical interest among scholars who saw the
enduring quality of his best work. And here's
where it gets really interesting for the novel's
legacy, World War II. Right. Gatsby gained massive
unexpected popularity when 123 ,000 Free Armed
Services Edition copies were distributed to American
soldiers overseas and to prisoners of war. This
introduced the novel to a massive new non -academic
audience, men who were fighting for America,
reading about its failed ideals. That distribution
was the catalyst. By 1960, the book was selling
100 ,000 copies per year. Today, it has sold
millions, is required reading, and is hailed
by some, like Charles Jackson, as the only flawless
novel in American literature and the strong contender
for the great American novel. Fitzgerald became
this cult figure by the 1950s, an Adonis of letters
who was more widely known than he ever was during
his lifetime. Adam Gopnik asserted that Fitzgerald,
contrary to his own samest lament that there
are no second acts in American lives, became
an enduring legend of the West. He found his
second act posthumously. His legacy is secured
by his style, which influenced so many later
writers like John O 'Hara and Richard Yates.
And his work has been adapted across every medium,
six major film versions of Gatsby alone. His
life story is constantly being retold, from Beloved
Infidel to Woody Allen's Midnight in Paris. So
what does this all mean? We've traced the arc
of his life, the glittering youth who became
the chronicler of the jazz age. The tragic descent
into alcoholism and financial ruin caused by...
by the need to maintain a cripplingly expensive
lifestyle. And the final critical recognition
that cemented his place in American letters.
He was the perpetual outsider who wrote the quintessential
story of what it means to be an American outsider.
And this returns us to that profound regret he
voiced to his daughter near the end of his life.
He wished he had prioritized the artist over
the careerist. That he should have finished Gatsby
and declared, I've found my line. From now on,
this comes first. This is my immediate duty.
Without this, I am nothing. And this begs the
essential provocative thought for you to consider.
If Fitzgerald had successfully prioritized the
artist over the careerist, could he have avoided
the tragic decline that followed his greatest
achievement? Or was the tragedy, the need for
status, the pursuit of the unattonable Ginevra,
and the demanding Zelda, the relentless consumption,
was that inherent to the very material that fueled
his greatest works in the first place? If he
had rejected the high life, would we even have
the Great Gatsby? That's the question his legacy
asks of all of us.