F. Scott Fitzgerald [author]

Calvin

Welcome to Headstones and Microphones where we use AI to step into the past through a researched, first-person simulation of history's most interesting people. I am your host, Calvin. While we’ve added some creative storytelling, our goal is to inspire your own study of these fascinating lives. Now, let’s meet our guest. Today, I am joined by one of the most celebrated voices of the Jazz Age. For those who may somehow not know who you are... who are you?

White Male Guest

Hello, Calvin. I am F. Scott Fitzgerald, a writer who tried his best to capture the glitter and the shadows of the American dream. Most people know me as the fellow who wrote The Great Gatsby.

Calvin

A legend! Let’s go back to the beginning. When and where were you born?

White Male Guest

I entered this world on September 24, 1896, in St. Paul, Minnesota.

Calvin

And what was your given name at birth?

White Male Guest

My full name was Francis Scott Key Fitzgerald.

Calvin

Is there a story behind your birth name?

White Male Guest

Oh, indeed! I was named after my distant cousin, Francis Scott Key—the very man who wrote the words to "The Star-Spangled Banner." It was quite a legacy to live up to, even as a small boy.

Calvin

That’s quite the claim to fame from day one! What was your hometown like growing up?

White Male Guest

St. Paul was a place of distinct social tiers. We lived on the periphery of the wealthy neighborhoods. I spent my time looking up at the big houses on Summit Avenue, always feeling like I was standing just outside the gates of a party I wasn't quite invited to yet.

Calvin

What was your family life like?

White Male Guest

It was a bit of a mixed bag. My father, Edward, was a man of great gentility but, unfortunately, not much business success. My mother, Molly, came from a family with a bit more money, which kept us afloat. There was always a sense of "genteel poverty"—trying to maintain appearances while the bank account whispered otherwise.

Calvin

What kind of kid were you?

White Male Guest

I was bright, restless, and perhaps a bit too eager to be liked. I was constantly writing—plays, poems, detective stories. I wanted to be the center of attention, the boy who could spin a tale that kept everyone listening.

Calvin

What were your biggest fears growing up?

White Male Guest

Failure. Plain and simple. I was terrified of being "average" or, worse, being forgotten. I also had a deep-seated fear of being poor, likely from watching my father struggle.

Calvin

What did you dream of becoming as a child?

White Male Guest

I wanted to be a hero! At first, I thought I’d be a great football star or a famous soldier. But eventually, the magic of the pen took over, and I knew I wanted to be a writer whose name would live forever in leather-bound books.

Calvin

What were some of your favorite activities in school?

White Male Guest

I lived for the drama club and the literary magazines. At Princeton, I spent far more time writing for the Tiger and the Triangle Club’s musical comedies than I did studying my Greek or math.

Calvin

What was your first job?

White Male Guest

After I left the Army, I worked for an advertising agency in New York, writing slogans for streetcar signs. I believe I wrote an ad for a laundry service! It wasn’t exactly "literature," but it paid the bills for a few months.

Calvin

Was there a moment where you realized you were different from everyone else?

White Male Guest

It was probably during my school years when I realized I could observe people—see their motivations and their flaws—and put them into words. I felt like an outsider looking in, which is a lonely feeling, but a vital one for a novelist.

Calvin

What’s a decision that changed everything for you, but felt small at the time?

White Male Guest

Joining the Army during the Great War. I never made it overseas, which I regretted at the time, but while I was stationed in Alabama, I met a girl named Zelda Sayre at a country club dance. That one night changed the entire trajectory of my life.

Calvin

Ah, the legendary Zelda! What was your biggest break?

White Male Guest

The publication of my first novel, This Side of Paradise, in 1920. It was an overnight sensation! Suddenly, I was the voice of my generation, and more importantly, I finally had enough money to convince Zelda to marry me.

Calvin

What were your biggest struggles before success?

White Male Guest

Rejection. I had a manuscript called The Romantic Egotist that was rejected multiple times. I used to pin the rejection slips to my wall. I was also desperately trying to prove I was worthy of Zelda, who wouldn't marry a man without a future.

Calvin

Did you ever consider quitting?

White Male Guest

In my heart? Never. But there were days in that advertising office where I felt the light fading. I just knew I had to keep rewriting until the world had no choice but to listen.

Calvin

Were there any specific daily habits or routines that you feel are essential to your success?

White Male Guest

I was a night owl. I did my best work in the quiet hours when the rest of the world was asleep. I’d write on large pads of paper, fueled by endless cigarettes and, quite often, a bit of gin to keep the ideas flowing—though that habit eventually became a bit of a hurdle!

Calvin

What job would you have had if fame never happened?

White Male Guest

I think I might have stayed in advertising. I had a knack for knowing what people wanted and how to sell them a dream. Or perhaps a failed Broadway lyricist!

Calvin

What was your life like before fame?

White Male Guest

It was a series of narrow escapes and high hopes. I was a young man in a uniform, dreaming of glory and writing poetry in the barracks, wondering if I’d ever leave a mark on the world.

Calvin

How did relationships change after success?

White Male Guest

Success turned our lives into a whirlwind. Zelda and I became the "Prince and Princess" of the Jazz Age. We were surrounded by people, but many were just there for the party. True friends became harder to distinguish from the sycophants.

Calvin

Did fame bring happiness?

White Male Guest

It brought excitement, certainly. It brought the Ritz in Paris and villas on the Riviera. But happiness? That was more fleeting. Fame is a bright light that can sometimes burn the very things you love.

Calvin

What was the downside of becoming famous?

White Male Guest

The pressure to stay on top. People expect you to be the life of the party forever. When the party ended and the Great Depression hit, the world wasn't as kind to the man who had celebrated the excess.

Calvin

What misconceptions did people have about you?

White Male Guest

Many thought I was just a "playboy" writer who didn't take the craft seriously. In truth, I was a perfectionist. I would labor over a single sentence for hours, trying to find the exact rhythm and color.

Calvin

What was your darkest moment?

White Male Guest

The 1930s were very difficult. Zelda’s health began to decline, and I felt my own creative spark flickering. I wrote an essay called "The Crack-Up" during that time—it was a very honest look at a man who felt he had lost his way.

Calvin

What past regrets did you carry, that you spoke about?

White Male Guest

I regretted not being more disciplined with my finances and my health. I often felt I had squandered the "gold" of my youth on things that didn't last.

Calvin

What’s something people misunderstood about your life?

White Male Guest

People often think The Great Gatsby was a huge hit when it came out. It actually had rather modest sales compared to my first book. It wasn't until much later that people realized what I was trying to say with that story.

Calvin

Tell me about a time when everything went wrong and how did you handle it?

White Male Guest

When I moved to Hollywood to write for the movies. I felt like a failure, a "hack" for hire. I handled it by putting my head down and starting work on what I hoped would be my comeback—a novel called The Last Tycoon. I worked on it until my very last breath.

Calvin

Who had the biggest influence on your life?

White Male Guest

Professionally, Ernest Hemingway—we had a complicated friendship, but he pushed me. Personally, it was always Zelda. She was my muse, my joy, and my greatest heartache.

Calvin

What was life like in your final years?

White Male Guest

It was quieter. I lived in Hollywood, working as a scriptwriter. I was trying to stay sober and focused on my craft, living a much more modest life than the one I had in France.

Calvin

What were you working on in your career before you passed away?

White Male Guest

I was deep into The Last Tycoon. I really believed it was going to be my best work—a true look at the machinery of Hollywood.

Calvin

When and where and how did you pass away and how old were you?

White Male Guest

I passed away on December 21, 1940, in Hollywood. It was a heart attack. I was only 44 years old.

Calvin

Far too young! What’s a random fact about you most people have never heard?

White Male Guest

I kept incredibly detailed ledgers! I recorded every penny I earned, every story I sold, and even a year-by-year summary of my life since I was a child. I was obsessed with tracking my own history.

Calvin

What’s the craziest rumor ever told about you?

White Male Guest

That Zelda and I once spent a whole night riding on top of a taxi cab through Manhattan. Actually... that one might have been true! We were quite spirited in those days.

Calvin

What was your most unique habit?

White Male Guest

I used to write on the backs of envelopes or any scrap of paper nearby if an idea hit me. I also had a habit of "boasting" about things I hadn't done yet, just to make them feel real.

Calvin

What was your favorite food?

White Male Guest

I quite enjoyed a good chicken salad and, of course, anything served at a grand dinner party. But in my later years, I lived on a lot of canned soup and crackers while I worked!

Calvin

What was your favorite book?

White Male Guest

I had a great love for Keats' poetry. As for novels, The Brothers Karamazov was a work I deeply admired.

Calvin

Did you have any known rivalries?

White Male Guest

Hemingway and I had a famous rivalry. We were "frenemies," I suppose you’d call it today. He thought I was too soft, and I thought he was a bit too obsessed with being "tough."

Calvin

Tell us a story nobody talks about.

White Male Guest

Once, in the South of France, I was so moved by a wandering musician that I gave him my watch because I had no cash on me. It was a beautiful, impulsive moment that felt like something out of a story.

Calvin

What’s your funniest behind-the-scenes moment?

White Male Guest

During my time in Hollywood, I was once fired from a film because the director didn't think I knew how to write "natural" dialogue. I was the highest-paid author in America at the time! I had to laugh at the irony.

Calvin

What advice would you give people chasing success?

White Male Guest

Don't confuse a "pleasant life" with a "creative life." Success is wonderful, but it’s the work—the actual sitting down and facing the blank page—that matters. And remember, there are no second acts in American lives... so make the first one count!

Calvin

Do you have any closing remarks about the interview or the stories you shared that you would like to share with the listeners before we sign off?

White Male Guest

Just that it has been a joy to speak again. Life is a beautiful, fleeting thing, much like a party that ends too soon. Treasure the stories you tell and the ones you live. Thank you for remembering me, Calvin.

Calvin

Thank you so much for being here, Scott. It’s been a fascinating look into the Jazz Age. And that wraps up another conversation from beyond the grave. Thanks for joining us on The Headstones and Microphones Podcast. Remember—legends may die, but their stories never do. Please help spread the word by sharing and following the pod.