F. Scott Fitzgerald’s Top 10 Short Stories | History Hit

F. Scott Fitzgerald’s Top 10 Short Stories

Image Credit: Public Domain, via Wikimedia Commons; History Hit

Essayist, novelist and short story writer F. Scott Fitzgerald (1896-1940) is considered to be one of the most important writers in American literary history. As the author of pivotal texts such as Tender is the Night (1934) and The Great Gatsby (1925), Fitzgerald was poet laureate of the ‘Jazz Age’, a term he popularised to convey rapidly changing consumerist, economic and sexual attitudes of 1920s America.

Fitzgerald first rose to fame aged 23 with the publication of This Side of Paradise (1920), and by the age of 30 had published his most famous work, The Great Gatsby. However, his own life was marred by alcoholism, financial problems and his wife’s mental illness, and half a decade later, the Great Depression had all but overshadowed his works.

When he died in 1940, he was largely considered a failure, despite publishing over 160 short stories in addition to his other works, many of which are still read and celebrated now.

Here’s our pick of F. Scott Fitzgerald’s 10 best short stories.


Bernice Bobs Her Hair

A scathing satire on the cruel gatekeeping of privileged young American women, Bernice Bobs Her Hair centres on a young woman who cuts her hair to make herself more popular amongst men. Bernice’s hair represents changing attitudes towards femininity during the flapper era, which prized more ‘boyish’ figures and haircuts, rather than the more traditionally ‘feminine’ styles worn by the older generation. Shorter hair styles were associated with more freedom. This is emphasised when a character mentions Louisa May Alcott, to which the character Marjorie Harvey responds: ‘Oh, please don’t quote Little Women! What modern girl could live like those inane females?’

An illustration of F. Scott Fitzgerald’s short story, ‘Bernice Bobs Her Hair.’ The artist is May Wilson Preston

Image Credit: May Wilson Preston, Public domain, via Wikimedia Commons

The Ice Palace

The Ice Palace is based upon a real ice palace that appeared at the 1887 Winter Carnival in St Paul, Minnesota, where Fitzgerald was born. Regarded as one of Fitzgerald’s most overtly modernist works, the novel follows Sally Happer, a young woman from Georgia, who travels north to meet her fiancé’s family. While in the ice palace, Happer has an epiphany that forces her to question her attitude towards her fiancé and overcome her disillusionment with the north. Like many of Fitzgerald’s characters, The Ice Palace features a protagonist who self-consciously rebels against Victorian ideas of femininity.

The Offshore Pirate

The Offshore Pirate revolves around a wealthy young woman called Ardita’s adventure with pirates. She is described as being excited about having an adventure, because her view on life is otherwise very negative. Ardita’s affections are competed for by the pirates, mirroring Fitzgerald’s own perceived unworthiness when vying for the hand of his future wife, Zelda. The way the short story is written mirrors Ardita’s own naivety, since the reader is similarly fooled by her plan. However, she is ultimately saved from a bad match by her uncle, which emphasises that though the era witnessed the rise of a political and social change for women, Fitzgerald suggests that certain new attitudes were short-sighted and selfish.

May Day

May Day is partly based on some events that Fitzgerald experienced in New York City. The story features themes of lost youth, wealth and two distinct but interrelated plots that the author revisited numerous times throughout his career. Set on 1 May 1919, the day on which violent protests in favour of ‘lower class’ rights took place, the short story follows a privileged group of Yale alumni who reunite for a dance. It examines the fallout of the devastation of World War One, as well as the hysteria that signalled the beginning of the Jazz Age.


The Curious Case of Benjamin Button

Probably Fitzgerald’s most famous short story, since it was adapted for the big screen in 2008 by David Fincher, The Curious Case of Benjamin Button tells the story of the titular character who is born in 1869 as a 70-year-old man and then ages backwards until he dies as a baby. He is the ultimate outsider, living life in an alternate and opposite trajectory to everyone else. The short story aims to challenge the idea that life might be better if we could erase all hurt; characters throughout deliver philosophical messages that ultimately remind the reader to cherish every day.

Illustration by James Montgomery Flagg depicting Benjamin Button (left)

Image Credit: F. Scott Fitzgerald, Public domain, via Wikimedia Commons

Winter Dreams

Winter Dreams is widely considered to be one of Fitzgerald’s finest works. The themes of loss and youthful illusions are largely modelled on the author’s own life, because of his own inability to seduce socialite Ginevra King, who later became the basis for the character Daisy Buchanan in The Great Gatsby. The story follows a young man from Minnesota who works at a local golf club, has his heart broken and then goes to fight in World War One. It prefigures The Great Gatsby – and is more closely associated with the novel than any of Fitzgerald’s other works – in that it focuses on the central character’s romantic infatuation and social climbing.

The Diamond as Big as the Ritz

The Diamond as Big as the Ritz parodies the staggering wealth amassed by barons such as John D. Rockefeller in 1920s America. It tells the fantastical story of a man called Braddock Washington who lives on a mountain-sized diamond in the Montana Rockies, that is indeed bigger than the Ritz hotel. The irony is that Washington’s net worth is far from stable, so if the diamond were offered for sale, the market would crash. Equally, there isn’t enough wealth in the world to buy the diamond. As a result, Washington must go to extreme lengths to keep the diamond’s existence a secret. In the short story, Fitzgerald satirises those who go to great lengths to preserve their ridiculous amounts of wealth, while questioning the transitory and abstract nature of money itself.


Hot and Cold Blood

Married couple Jim and Jaqueline Mathers have saved all of their money for the imminent birth of their child. However, Jim is a generous man who always aims to support those in need; he cares for friends and strangers alike, lends money without a second thought and fails to put his family first. Jim finally listens to his wife’s implorations that he support her and their unborn child first, which pains him. However, he never realises that in giving his money away, he himself might become someone in need. Here, Fitzgerald draws attention to shallow, selfish and consumerist nature of 1920s America in contrast with the perhaps naïve generosity of the protagonist.

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Babylon Revisited

Unlike Fitzgerald’s works which depict the Jazz Age of the 1920s, this short story examines the fallout of the 1929 Wall Street Crash, though does indeed contain flashbacks to the hedonistic years from earlier in the decade. The story follows Charlie Wales, a man haunted by his past mistakes since his extravagance cost him and his family their savings, and landed him in a sanitorium. Fitzgerald uses the deteriorating relationship between Wales, his wife and daughter to draw attention to the cost of careless, extravagant living upon less tangible values such as family.


The Lost Decade

One of Fitzgerald’s shortest works, The Lost Decade examines the effects of drink and how it leads people to forget their surroundings, become isolated from reality and lose touch with themselves. Published just one year before Fitzgerald died, the short story largely parallels the author’s own struggle with alcoholism as well as his feelings of social isolation and failure to appreciate the everyday. In December 1940, Fitzgerald died, believing himself a failure, and perceived by those around him as a washed-up alcoholic, the embodiment of the former decadence of the Jazz Age.

Lucy Davidson