1. He was named after a famous ancestor.

Francis Scott Key Fitzgerald was born in St. Paul Minnesota on September 24, 1896. He was named for Francis Scott Key, the lawyer and writer who penned the lyrics to “The Star Spangled Banner” during the War of 1812. The two were only distantly related—Key was a second cousin three times removed—but Fitzgerald was known to play up the family connection. While driving past a statue of Key in an alcoholic haze in 1934, he supposedly hopped from the car and hid in the bushes, yelling to a friend, “Don’t let Frank see me drunk!”

2. He was a poor student and an atrocious speller.

Fitzgerald read widely and demonstrated an early talent for writing, but he was a lousy student who struggled to achieve passing marks in both grade school and college. He had a penchant for cutting classes during his time at Princeton University and nearly failed out before abandoning his studies to join the military. Despite his legendary command of the written word, Fitzgerald was also a poor speller and may have suffered from dyslexia. After reading a typo-filled version of “This Side of Paradise,” literary critic Edmund Wilson—a classmate of Fitzgerald’s during his Princeton days—declared it “one of the most illiterate books of any merit ever published…full of English words misused with the most reckless abandon.”

3. He narrowly missed out on serving in World War I.

When the United States entered World War I in 1917, Fitzgerald dropped out of Princeton and took a commission as a second lieutenant in the army. Worried he might die in battle, he began frantically writing in his off-hours in the hopes of leaving behind a literary legacy. While he never made it to the battlegrounds of World War I—the November 1918 armistice was signed shortly before he was to be shipped overseas—Fitzgerald did complete a draft of an unpublished novel called “The Romantic Egotist,” which he later reworked into his smash hit debut “This Side of Paradise.”

4. His wife Zelda was considered the quintessential 1920s “flapper.”

Shortly after the publication of “This Side of Paradise,” Fitzgerald married Zelda Sayre, the daughter of an Alabama judge. Beautiful and unpredictable, Zelda was a major inspiration for the new generation of liberated “flapper” girls Fitzgerald often wrote about in his novels and stories. She smoked and drank in public, cracked risqué jokes and was an accomplished painter, dancer and writer. The couple’s fashionable clothes and booze-fueled antics made them the toast of the literary world—writer Ring Lardner even called them “the prince and princess of their generation”—but their glamorous lives were later visited by tragedy in the 1930s. Fitzgerald sank into alcoholism and struggled to write, and Zelda suffered a mental breakdown and spent the latter part of her life in and out of sanitariums.

5. He kept an extraordinarily detailed record of his life.

Between 1919 and 1937, Fitzgerald obsessively recorded the progress of his life and career in a large, leather-bound business ledger. Much of the ledger is dedicated to recording his published works as a writer and his income, but one section, titled “Outline Chart of My Life,” provides a month-by-month account of his activities since birth. Fitzgerald documented everything from his first word (“up”), to his height at age 13 (5’3’), to the date he fell in love with Zelda (September 7, 1918). Many years also include a brief summary sentence. Age 14 is described as “A Year of Much Activity but Dangerous,” while the headline for 1920—the year he first found fame—reads “Revelry and Marriage. The rewards of the year before.”

6. He never lived in the same place for more than a few years.

Despite earning a small fortune as a writer, Fitzgerald never owned a home and spent most of his life living out of rented houses, apartments and high-class hotels. Between 1920 and 1940, he lived variously in New York City, Connecticut, Minnesota, Long Island, Paris, the French Riviera, Rome, Los Angeles, Delaware, Switzerland, Baltimore and North Carolina. Fitzgerald’s itinerant nature was due in part to his attempts to escape his hard-partying lifestyle and find peace and quiet to write, but he also occasionally moved to cities where his mentally ill wife Zelda was being hospitalized.

7. He had a rocky friendship with Ernest Hemingway.

The macho Hemingway and the urbane Fitzgerald might seem like an odd pairing, but the two authors struck up a fast friendship after meeting in Paris in 1925. Their relationship was complicated by Hemingway’s intense dislike of Zelda Fitzgerald, whom he described as “crazy” and a distraction to her husband’s writing. The literary titans drifted apart during the late-1920s, and Hemingway later bashed Fitzgerald in print on more than one occasion. By 1937, Fitzgerald lamented that their friendship was as good as finished. “I talk with the authority of failure,” he wrote. “Ernest with the authority of success. We could never sit across the table again.”

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8. His most famous work was considered a flop upon its release.

Despite winning rave reviews from the likes of T.S. Eliot and Edith Wharton, Fitzgerald’s 1925 masterpiece “The Great Gatsby” was never a bestseller in his lifetime. It performed poorly compared to his first two novels, selling just over 20,000 copies and only turning a meager profit for its publisher. Popular interest in the book didn’t spike until World War II when some 150,000 copies were shipped to U.S. servicemen overseas. Combined with other posthumous re-releases of his work, this “Armed Services Edition” helped revive Fitzgerald’s literary reputation and secure “The Great Gatsby” a place among the most beloved American novels. The book now sells some 500,000 copies each year.

9. He worked as a Hollywood screenwriter.

Following a series of career setbacks and repeated attempts to quit drinking, Fitzgerald moved to Los Angeles in 1937 and took a job as a screenwriter with the film studio MGM. He spent over two years working as an uncredited script doctor on such films as “Gone with the Wind” and “A Yank at Oxford,” but his own scripts—including proposed projects for Greta Garbo and Joan Crawford—were almost universally rejected. In the end, the famous novelist achieved just one Hollywood credit for writing on a 1938 film called “Three Comrades.” “I just couldn’t make the grade as a hack,” Fitzgerald quipped after one of his studio contracts was terminated. “That, like everything else, requires a certain practiced excellence.”

10. He died before finishing his final novel.

In 1940, Fitzgerald began writing “The Love of the Last Tycoon,” a novel inspired by his experiences working in the trenches of Hollywood. He was in debt and still struggling to remain sober, but he believed his work-in-progress showed considerable promise. “It will, at any rate, be nothing like anything else as I’m digging it out of myself like uranium,” he wrote to Zelda in November. Only a month later, Fitzgerald suffered a heart attack and died at the age of 44, leaving his comeback novel incomplete. A version of “The Love of the Last Tycoon” was published a year later, however, and even though the book was only half-finished, many critics hailed it as Fitzgerald’s most accomplished work.