Looking at this cool, calm, collected portrait of F. Scott Fitzgerald one might think the young, famous author was living the good American life…

But Fitzgerald’s life was nothing short of miserable by this time. Like Fitzgerald’s own character Gatsby, he met Zelda at a young age and they fell in love, only to find their love was held back by money. She called off her engagement to Fitzgerald for his poverty. At the time he was working at an advertising agency earning a meager $90 a month. He began publishing stories in magazines on the side and going back and forth with a publishing house on his first novel. They would reject it but with notes encouraging changes and resubmission. It was finally accepted with significant revisions after his third attempt, and then he married Zelda. Even after he found decent success as a novelist (he was never nearly as famous in his lifetime as he is now) and a romancer, he still suffered at the hands of the American Dream.

Even though he’d already published "The Great Gatsby," "The Beautiful and the Damned," and many popular short stories, it was his personal life that really suffered. His wife, Zelda, struggled with extreme mental health issues and breakdowns, and she moved in and out of a sanitarium in Ashland, Georgia. She eventually died there in a tragic sanitarium fire in 1948. Meanwhile, Fitzgerald lived a raging life of excess, allegedly drinking thirty beers a day or a full quart of gin depending what he was in the mood for. Despite his decent success as a writer, they couldn’t afford their lifestyle what with the medical bills, the daily thirty packs, and the lavish parties he threw.

When F. Scott Fitzgerald commissioned David Silvette to do his portrait in 1935, it may come as no surprise that he fell through on his payment. He never actually owned the piece. That said, it’s the only portrait of Fitzgerald done from real life. Still, Silvette spent much of his long career doing portraits, many of which were quite famous (like Thomas Jefferson), and many of whom were Confederate generals…

He eventually fell prey to his own decadent lifestyle and was forced to work on screenplays in Hollywood to pay off his debts up until his death of a heart attack in 1940.