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20 Enchanting Books Like “The Great Gatsby” For Jazz Age Lovers

Step Back in Time With These Classics Similar to "The Great Gatsby"
by The Blinkist Team | Apr 3 2024

20 Enchanting Books Like The Great Gatsby - Jazz Age Reads

“The Great Gatsby” by F. Scott Fitzgerald is an iconic portrayal of the Roaring Twenties’ glitz, glamour, and the elusive American Dream. Its intricate examination of desire, obsession, and the high life of the Jazz Age has captured the imaginations of readers for generations.

If Jay Gatsby’s tragic pursuit and the decadent world of West Egg have left you yearning for more tales from a bygone era filled with complex characters and societal critiques, you’re in the perfect spot. Below, uncover a curated list of 20 books that echo the themes, setting, and allure of “The Great Gatsby”, ensuring your literary journey through the dazzling 1920s continues.

Top 20 best books to read if you liked “The Great Gatsby” by F. Scott Fitzgerald


1. “This Side of Paradise” by F. Scott Fitzgerald

Delve into Fitzgerald’s debut novel, which charts the coming of age of Amory Blaine as he navigates love and social stratification post-World War I.

Elements in common with “The Great Gatsby”:

  • A critical look at the American elite’s aspirations and moral decay.
  • Lush, evocative prose that captures the zeitgeist of the era.
  • Themes of love, wealth, and societal expectation.


2. “The Beautiful and Damned” by F. Scott Fitzgerald

Follow the story of Anthony and Gloria Patch, a couple entangled in the pursuit of happiness through wealth and status, mirroring Gatsby’s thematic preoccupations.

Elements in common with “The Great Gatsby”:

  • Exploration of the Jazz Age’s excesses and moral bankruptcy.
  • A focus on flawed characters and their tragic flaws.
  • Critique of the American Dream’s illusion.


3. “Z: A Novel of Zelda Fitzgerald” by Therese Anne Fowler

Experience the Jazz Age through the eyes of Zelda Fitzgerald, an icon of the 1920s in this vivid fictionalized account of her tumultuous life with Scott.

Elements in common with “The Great Gatsby”:

  • A portrayal of the Jazz Age’s glamour and downfall.
  • Insight into the lives of the era’s literary elite.
  • Themes of love, madness, and the price of fame.


4. “The Sun Also Rises” by Ernest Hemingway

Embark on a journey with the Lost Generation from the nightlife of 1920s Paris to the brutal bullfighting rings of Spain.

Elements in common with “The Great Gatsby”:

  • Post-war disillusionment and the search for meaning.
  • A critique of the “lost generation’s” hedonism and aimlessness.
  • Sharp, minimalist prose depicting complex emotional landscapes.


5. “Jazz” by Toni Morrison

Morrison’s novel set in Harlem during the 1920s explores themes of love, violence, and the African American experience, with jazz music flowing through its heart.

Elements in common with “The Great Gatsby”:

  • A narrative driven by passion, obsession, and tragedy.
  • Vivid portrayal of the 1920s setting.
  • Complex characters navigating societal constraints.


6. “Vile Bodies” by Evelyn Waugh

Dive into the frenetic world of young, carefree London society between the wars, chronicling their parties, romances, and eventual disillusionments.

Elements in common with “The Great Gatsby”:

  • Satire of the shallow, hedonistic lifestyle of the elite.
  • Themes of love amidst the chaos of a changing world.
  • Critical examination of the pursuit of pleasure and its pitfalls.


7. “The Paris Wife” by Paula McLain

Discover the story of Hadley Richardson, Hemingway’s first wife, set against the backdrop of Jazz Age Paris, as they navigate love and ambition.

Elements in common with “The Great Gatsby”:

  • An intimate look at the complexities of love and marriage.
  • The 1920s setting rich in artistic and cultural revolution.
  • Themes of identity and personal transformation amidst societal upheaval.


8. “Brideshead Revisited” by Evelyn Waugh

Explore the tale of Charles Ryder and his entanglement with the aristocratic Flyte family, set between the wars in England’s grand estates.

Elements in common with “The Great Gatsby”:

  • Themes of nostalgia, class, and the decline of the English aristocracy.
  • A poignant exploration of love, faith, and longing.
  • Rich, evocative descriptions of time and place.


9. “Gentlemen Prefer Blondes” by Anita Loos

Laugh along with Lorelei Lee, a beautiful, young gold-digger navigating society in pursuit of a rich husband, told through her witty diary.

Elements in common with “The Great Gatsby”:

  • A humorous look at the 1920s social and dating scenes.
  • Satirical portrayal of the era’s materialism and class obsession.
  • Sharp, witty prose highlighting societal norms and extravagance.


10. “The Age of Innocence” by Edith Wharton

Step into New York’s high society of the 1870s, where Newland Archer must choose between duty and passion in this Pulitzer Prize-winning novel.

Elements in common with “The Great Gatsby”:

  • A critical view of upper-class society and its unwritten rules.
  • Richly detailed descriptions of the setting and era.
  • Themes of passion, duty, and societal constraints.


11. “Mrs. Dalloway” by Virginia Woolf

Spend a day with Clarissa Dalloway as she prepares for a high-society party in post-war London, exploring the complexities of life and love.

Elements in common with “The Great Gatsby”:

  • A deep dive into the psyche of complex characters.
  • The backdrop of a society reeling from the effects of war.
  • Stream-of-consciousness narrative capturing the fleeting nature of time.


12. “An American Tragedy” by Theodore Dreiser

Traverse the dark side of the American Dream through Clyde Griffiths, who seeks wealth and status but finds tragedy in his immoral pursuits.

Elements in common with “The Great Gatsby”:

  • Themes exploring the destructive pursuit of the American Dream.
  • A focus on the social divide and its implications.
  • A tragic narrative examining the consequences of ambition and desire.


13. “The Razor’s Edge” by W. Somerset Maugham

Follow Larry Darrell’s quest for spiritual meaning, leading him from Chicago’s high society to the ashrams of India post-World War I.

Elements in common with “The Great Gatsby”:

  • Characters disillusioned by the materialism of their society.
  • A journey of self-discovery against the backdrop of changing times.
  • Philosophical exploration of life’s deeper meanings beyond wealth.


14. “Save Me the Waltz” by Zelda Fitzgerald

Experience the Jazz Age’s excitement and excess through Alabama Beggs’ eyes, reflecting Zelda Fitzgerald’s own ambitions and struggles.

Elements in common with “The Great Gatsby”:

  • A vivid portrayal of the 1920s and its defining characteristics.
  • Themes of ambition, love, and the quest for identity.
  • Insight into the highs and lows of the creative and destructive lifestyle of the era.


15. “Passing” by Nella Larsen

Delve into the lives of two African American women who can “pass” as white but choose different paths in 1920s New York, exploring themes of identity and race.

Elements in common with “The Great Gatsby”:

  • Examination of societal norms and the consequences of challenging them.
  • A 1920s setting that influences the characters’ lives and choices.
  • Complex characters dealing with issues of identity and belonging.


16. “Manhattan Transfer” by John Dos Passos

Get lost in the interwoven stories of New Yorkers in the early 20th century as they chase success, survival, and meaning in a changing city.

Elements in common with “The Great Gatsby”:

  • A mosaic narrative capturing the essence of an era.
  • Characters striving for success in a rapidly evolving society.
  • Critique of the American Dream and its many dimensions.


17. “The Diviners” by Libba Bray

Immerse yourself in a supernatural twist on the 1920s, where a group of teenagers with peculiar abilities confront a malevolent force amidst the Jazz Age glitz.

Elements in common with “The Great Gatsby”:

  • The 1920s setting filled with glamour and darkness.
  • Themes of desire, ambition, and the supernatural.
  • A richly drawn world that blends historical detail with fantasy.


18. “The Chaperone” by Laura Moriarty

Follow the story of a Kansas woman who chaperones a young Louise Brooks to New York City in the 1920s, embarking on a journey of self-discovery.

Elements in common with “The Great Gatsby”:

  • Exploration of societal changes and personal freedoms in the 1920s.
  • Rich historical detail that paints a vivid picture of the era.
  • Themes of identity, morality, and the impact of the past on the present.


19. “Rules of Civility” by Amor Towles

Navigate the twists of fate and fortune that take Katey Kontent from the secretarial pool to high society in late 1930s New York.

Elements in common with “The Great Gatsby”:

  • An exploration of social climbing and the allure of wealth.
  • Vibrant descriptions of New York life and the era’s extravagances.
  • Complex characters navigating love, ambition, and societal norms.


20. “The Paying Guests” by Sarah Waters

Experience the post-war 1920s in London through the lives of Frances Wray and her mother, who take in lodgers, leading to forbidden love and unforeseen consequences.

Elements in common with “The Great Gatsby”:

  • A detailed portrayal of the period bringing historical and social context.
  • Themes of love, desire, and the breaking of societal conventions.
  • A narrative that builds tension and explores moral complexities.

In conclusion, the enduring allure of “The Great Gatsby” lies in its timeless critique of the American Dream, its complex characters, and the lush depiction of the Jazz Age. The books on this list offer a similar journey into the realms of luxury, societal critique, and the pursuit of meaning amid the chaos of changing times.

Whether you’re longing for more tales of romance, ambition, or a deep dive into the socio-political landscapes of the 1920s, these selections promise to carry you away to another era. Happy reading!


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