Discover 11 Timeless Books like The Great Gatsby

Imagine stepping into an era of timeless elegance, where glitz, glamour, and human drama collide in a symphony of storytelling. That’s the magic of F. Scott Fitzgerald’s masterpiece, ‘The Great Gatsby.’ If you’ve ever been entranced by the opulent parties, mysterious characters, and the exploration of the American Dream within those pages, you’re about to embark on a literary journey you won’t want to miss.

Books Like the Great Gatsby

In this carefully curated selection, we’re about to introduce you to novels that will spirit you away to different times and places, all while exploring themes of wealth, ambition, and societal transformation. Whether you’re a die-hard Gatsby fan or someone seeking the enchantment of the Roaring Twenties for the first time, these recommendations for books like the Great Gatsby promise to ignite your imagination and immerse you in stories that have captivated hearts for generations.

Nick (2021)

by Michael Farris Smith (prequel)

If you loved reading ‘The Great Gatsby,’ I believe that the perfect book to start this list with would be its prequel, written by Michael F. Smith.

In the midst of World War I, a young Nick Carraway envisions his beloved Ella in Paris and reminisces about his wholesome upbringing in the Midwest with his Minnesota parents.

However, alongside these thoughts, a darker sense of disconnection plagues him. “A life torn apart. A mind torn apart.” This is the version of Nick we meet during his leave in Paris, struggling and mostly failing to reconcile the horrors of war with what is commonly referred to as reality.

If you want to know who Nick was before ‘Gatsby’ this book is an absolute must-read.

The Chosen and the Beautiful (2021)

by Nghi Vo

In ‘The Chosen and the Beautiful’ by Nghi Vo, you’ll find a remarkable reimagining of F. Scott Fitzgerald’s beloved classic, ‘The Great Gatsby.’ What sets this book apart is its narrative perspective, as it’s told from the viewpoint of Jordan Baker, a character we know from the original story.

In case you’re wondering why this book and the previous one were both published in 2021, well, the authors had to basically wait till the copyright on ‘The Great Gatsby’ expired.

Jordan, an adopted Vietnamese American, takes center stage and invites readers into the dazzling world of 1920s America.

Amid the glamour, lavish parties, and intricate societal norms of the Jazz Age, the novel breathes new life into well-known characters like Jay Gatsby and Daisy Buchanan. As we follow Jordan’s journey, the story explores deep themes such as identity, race, privilege, and the relentless pursuit of the American Dream—all set against the backdrop of the exhilarating Roaring Twenties.

What makes ‘The Chosen and the Beautiful’ truly stand out is its infusion of magical and mystical elements, adding an extra layer of intrigue to the narrative. For those in search of books reminiscent of ‘The Great Gatsby,’ Nghi Vo’s reimagining offers a fresh and captivating take on familiar characters and themes, making it a must-read for anyone who holds a special place in their heart for Fitzgerald’s classic.

The Sun Also Rises (1926)

by Ernest Hemingway

Set in the aftermath of World War I, ‘The Sun Also Rises’ follows a group of expatriates who gather in Paris and later travel to Pamplona, Spain, to witness the running of the bulls and participate in the fiesta. The story is narrated by Jake Barnes, a wounded American veteran and journalist, and revolves around his complex relationships with Lady Brett Ashley, a beautiful but promiscuous Englishwoman, and his expatriate friends, including Robert Cohn, an aspiring writer, and Mike Campbell, a Scottish war veteran.

Through the characters’ hedonistic lifestyle, the novel portrays the emptiness and moral decay of post-war society. As they seek solace in parties, alcohol, and bullfighting, they struggle to find meaning and purpose in a world that seems devoid of values.

This novel portrays the extravagant and lavish lifestyle of the characters, and if that is one of the reasons why you loved reading ‘The Great Gatsby,’ you’ll love reading this novel, too.

Tender is the Night (1934)

by F. Scott Fitzgerald

Set in the 1920s, ‘Tender is the Night’ follows the lives of Dick and Nicole Diver, a glamorous and seemingly perfect couple living in the wealthy expatriate community of the French Riviera. The story unfolds through the eyes of Rosemary Hoyt, a young actress who becomes infatuated with Dick and gradually becomes entangled in their marriage.

As the narrative progresses, the facade of perfection surrounding the Divers begins to crack, revealing their inner struggles and emotional frailties. Dick’s descent into alcoholism and Nicole’s deteriorating mental health add layers of tension and tragedy to their relationship.

This novel also has that decadent feel to it, along with being plenty rich in prose, and explores themes of love, identity, and the corrupting influence of wealth and success. ‘Tender is the Night’ will definitely remind you of ‘The Great Gatsby,’ making it a must-read.

This Side of Paradise (1920)

by F. Scott Fitzgerald

The novel is divided into three sections, each representing a different phase of the protagonist, Amory’s life.

Amory Blaine is a young man born into privilege in the early 20th century. In the first section, he is a young student at Princeton University, where he indulges in intellectual pursuits and romantic relationships. He becomes disillusioned with his studies and his idealistic notions of love as he encounters the realities of the world.

The second section sees Amory struggling to find his place in society after leaving college. He moves to New York City, engaging in various jobs and relationships while grappling with his own identity and the changing social landscape of the post-World War I era.

The final section depicts Amory’s journey of self-discovery as he reflects on his past, confronts his failures and aspirations, and contemplates his future. Ultimately, the novel explores themes of love, ambition, societal expectations, and the elusive pursuit of happiness, capturing the spirit of the Jazz Age and the uncertainties of a generation seeking its place in the world.

Mrs. Dalloway (1925)

by Virginia Woolf

This book explores a single day in the life of Clarissa Dalloway, an upper-class woman in post-World War I London. The story delves into the complexities of Clarissa’s mind as she prepares to host a party in the evening.

Throughout the day, Woolf delves into Clarissa’s inner thoughts and memories, revealing her insecurities, regrets, and desires. The narrative also shifts perspectives, offering glimpses into the lives of other characters, including Septimus Warren Smith, a war veteran suffering from mental anguish.

As the day unfolds, Clarissa reflects on her past, her choices, and the constraints of societal expectations. She contemplates her relationships with her husband, Richard, her former lover, Peter Walsh, and her daughter, Elizabeth.

The novel examines themes of identity, social class, gender roles, and the effects of war on individuals, which makes it a must-read if you liked ‘The Great Gatsby.’

The Age of Innocence (1920)

by Edith Wharton

‘The Age of Innocence’ is a captivating novel set in 1870s New York City, depicting the society’s rigid rules and constraints. The story revolves around Newland Archer, a young man from a wealthy and respected family, who becomes engaged to the beautiful and conventional May Welland. However, when May’s unconventional cousin, Countess Ellen Olenska, returns from Europe seeking a divorce, Archer is drawn to her independent spirit and free thinking.

Despite their growing attraction, Archer is torn between societal expectations and his desire for personal happiness. Wharton masterfully explores themes of love, duty, tradition, and the clash between individual desires and societal pressures.

The novel is renowned for Edith Wharton’s meticulousness in capturing the intricacies of the 19th-century upper-class lifestyle on the East Coast of America. The novel stands out not only for its precise depiction of this social stratum but also for the tragic unfolding of its plot. Wharton, who was 58 years old when the book was published, possessed firsthand experience of the world she portrayed, having witnessed its profound transformation during and after World War I.

Rules of Civility (2011)

by Amor Towles

The novel begins on New Year’s Eve in 1937 when Katey and her friend Eve, both young and striving for success, encounter the enigmatic and wealthy Tinker Grey. This chance meeting sets the stage for a series of events that will change their lives forever.

As Katey navigates the upper echelons of New York society, she encounters a cast of intriguing characters, including the charming but elusive Tinker, and Wallace Wolcott, a writer with an air of mystery about him. Against the backdrop of glamorous parties and jazz-filled nights, Katey grapples with ambition, love, and the pursuit of the American Dream.

“Rules of Civility” is a story of ambition, class, and the pursuit of a better life, mirroring some of the themes found in “The Great Gatsby.” The novel explores the complexities of human relationships and the allure of the American Dream during a time of significant social change.

Brideshead Revisited (1945)

by Evelyn Waugh

“Brideshead Revisited” by Evelyn Waugh is a beautifully written novel that takes readers on a journey through the lives of the British aristocracy during the early 20th century.

The story is narrated by Charles Ryder, a young and aspiring artist who becomes enamored with the world of the wealthy and privileged after he befriends Sebastian Flyte, a charming and eccentric young man. Charles is introduced to Sebastian’s family, the Marchmains, and their magnificent ancestral home, Brideshead Castle.

As Charles becomes increasingly intertwined with the lives of the Marchmain family, he is drawn into their complex web of relationships and their opulent lifestyle. He becomes captivated not only by Sebastian but also by Sebastian’s sister, Julia, with whom he forms a deep and complicated connection.

Against the backdrop of the grandeur and decadence of the British upper class, “Brideshead Revisited” explores themes of love, class, religion, and the passage of time. The novel delves into the lives of its characters as they grapple with their desires, responsibilities, and the inevitable changes that come with the passage of time

The Beautiful and Damned (1922)

by F. Scott Fitzgerald

“The Beautiful and Damned” by F. Scott Fitzgerald is a captivating exploration of the Jazz Age and the pursuit of the American Dream during the early 20th century.

The novel revolves around the lives of Anthony Patch and his wife, Gloria Gilbert, a young and glamorous couple living in New York City. Anthony is an heir to a substantial fortune, and the couple leads a life of decadence, partying, and extravagance. They are beautiful and seemingly destined for a life of leisure.

However, their recklessness, lack of purpose, and dependence on inherited wealth lead to their gradual moral and financial decline.

As their marriage deteriorates, Anthony struggles to find a meaningful purpose in life, and Gloria seeks escape in the arms of other men. Their self-destructive behaviour eventually leads to financial ruin and a sense of emptiness.

The protagonist in this novel, like in ‘The Great Gatsby’ is an ambitious individual who strives for success and recognition in society. They’re both driven by their desires but ultimately face personal and moral failures. If that part of ‘The Great Gatsby’ intrigued you, you definitely must give this novel a read.

Day of the Locust (1939)

by Nathanael West

Like ‘The Great Gatsby,’ this novel also presents a critique to the American dream. A dark and satirical novel, ‘Day of the Locust’ revolves around a cast of eccentric and disillusioned characters who are consumed by the shallow and artificial world of the entertainment industry.

The protagonist, Tod Hackett, is a young artist working as a set designer in the film industry. He becomes infatuated with Faye Greener, an aspiring actress and object of desire for many men. As Tod immerses himself in the glitz and glamour of Hollywood, he witnesses the emptiness and corruption beneath the surface.

The novel explores themes of failed dreams, desperation, and the dehumanizing effects of a society driven by greed and ambition. As tensions rise, the narrative reaches a climactic and chaotic finale during a riot at a film premiere, symbolizing the destructive nature of the Hollywood dream.

Conclusion to Books Like the Great Gatsby

And there you have it, 11 Books Like the Great Gatsby!

As we wrap up our literary journey through these captivating novels, we hope you’ve discovered a treasure trove of stories that capture the essence of ‘The Great Gatsby’ in their own unique ways. These 11 books like the Great Gatsby have taken us on diverse journeys, from the glitz and glamour of the 1920s to modern tales of ambition, love, and the human condition.

Whether you’re searching for more mysterious characters, opulent settings, or reflections on the American Dream, these recommendations cater to all lovers of F. Scott Fitzgerald’s timeless masterpiece. So, pick up one of these novels, let their words transport you to different times and places, and immerse yourself in stories that continue to touch our hearts. May your reading adventures be as rich and rewarding as the one we’ve shared here. Happy reading!

However, if you want even more books like the Great Gatsby you should consider-

1. The Amazing Adventures of Kavalier and Clay by Michael Chabon
2. The Mysteries of Pittsburgh by Michael Chabon
3. The Rum Diary by Hunter S. Thompson
4. Appointment in Samarra by John O’Hara
5. Play It as It Lays by Joan Didion
6. The Picture of Dorian Gray by Oscar Wilde
7. Garden by the Sea by Mercè Rodoreda
8. Passing by Nella Larsen
9. Catcher in the Rye by J. D. Salinger
10. Bel Canto by Ann Patchett
11. Beautiful Little Fools by Jillian Cantor
12.  The Green Hat by Michael Arlen
13. The House of Mirth by Edith Wharton
14. My Summer Friend by Ophelia Rue
15. The Razor’s Edge by Somerset Maugham
16. A Prayer for Owen Meany by John Irving
17. Miss Lonelyhearts by Nathanael West
18. The Dream Merchants by Robbins