The Greatest Fiction Books of All Time on Failure

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This list represents a comprehensive and trusted collection of the greatest books. Developed through a specialized algorithm, it brings together 401 'best of' book lists to form a definitive guide to the world's most acclaimed books. For those interested in how these books are chosen, additional details can be found on the rankings page.

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Failure

The "Failure" category in literature encompasses a diverse range of books that delve into the multifaceted concept of failure, exploring its implications, causes, and consequences across various contexts. These works may include personal memoirs recounting individual setbacks, business and entrepreneurial narratives detailing corporate collapses, and philosophical or psychological treatises examining the nature of failure and its role in human growth and resilience. Additionally, this genre often highlights stories of redemption and lessons learned, offering readers insights into how failure can serve as a catalyst for innovation, self-discovery, and ultimately, success. By confronting the often stigmatized and misunderstood notion of failure, these books provide a nuanced perspective that encourages readers to embrace and learn from their own missteps.

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  1. 1. A Confederacy of Dunces by John Kennedy Toole

    The novel is a comedic satire set in New Orleans in the early 1960s, centered around Ignatius J. Reilly, a lazy, eccentric, highly educated, and socially inept man who still lives with his mother. Ignatius spends his time writing a lengthy philosophical work while working various jobs and avoiding the responsibilities of adulthood. The story follows his misadventures and interactions with a colorful cast of characters in the city, including his long-suffering mother, a flamboyant nightclub owner, a beleaguered factory worker, and a frustrated hot dog vendor.

    The 200th Greatest Book of All Time
  2. 2. Of Human Bondage by W. Somerset Maugham

    The novel follows the life of Philip Carey, a club-footed orphan who struggles with his disability and his passionate and unrequited love for a destructive woman. His journey takes him from a strict religious upbringing in England to an adventurous life in Paris where he attempts to become an artist before finally settling into a career in medicine. The story is a powerful exploration of human desire, ambition, and the search for meaning in life.

    The 220th Greatest Book of All Time
  3. 3. The Fountainhead by Ayn Rand

    The novel presents the story of an innovative architect, who values his individualism and creativity above all else. He refuses to conform to traditional architectural designs, which leads to his struggle against a system that rewards mediocrity and conformity. Despite numerous setbacks and rejections, he remains true to his unique vision and principles. The book explores themes of objectivism, individualism, and capitalism, challenging the reader to consider the value of standing alone against the collective.

    The 417th Greatest Book of All Time
  4. 4. Bouvard et Pécuchet by Gustave Flaubert

    "Bouvard et Pécuchet" is a satirical novel that chronicles the lives of two Parisian copy clerks, Bouvard and Pécuchet, who decide to retire in the countryside after unexpectedly inheriting a fortune. Their attempts to become gentlemen farmers are thwarted by a series of comical failures. The pair then embarks on a quest for knowledge in various fields such as medicine, literature, politics, and religion, but their efforts lead to more confusion and absurdity. The novel is a critique of intellectual pretensions and a commentary on the futility of human endeavor.

    The 428th Greatest Book of All Time
  5. 5. The Day of the Locust by Nathanael West

    "The Day of the Locust" is a novel set in 1930s Hollywood, portraying the dark side of the American dream through the lives of its desperate characters. The protagonist, a young artist from the East Coast, finds himself disillusioned by the superficiality and decay of Hollywood society, which is filled with failed actors, charlatans, and lost souls. The narrative culminates in a violent riot, symbolizing the destructive power of frustrated dreams and the harsh reality of the American dream.

    The 464th Greatest Book of All Time
  6. 6. New Grub Street by George Gissing

    "New Grub Street" is a novel set in the literary and journalistic circles of 1880s London. The story revolves around two writers, one who seeks wealth and status and the other who values artistic integrity over material success. It provides a stark and realistic portrayal of the struggles faced by writers, including financial hardship, the pressure to compromise artistic integrity for commercial success, and the destructive effects of these pressures on personal relationships and mental health. The book is a critique of the commercialization of literature and journalism during the period, and a commentary on the conflict between art and commerce.

    The 516th Greatest Book of All Time
  7. 7. Lost Illusions by Honoré de Balzac

    The Two Poets

    "Lost Illusions" is a sweeping narrative that focuses on the life of a young, ambitious poet from the provinces who moves to Paris in hopes of making a name for himself. Over time, he becomes disillusioned with the corruption and moral decay of the city's literary and high society circles. The protagonist's journey is marked by his struggle to maintain his integrity and idealism in a world dominated by materialism and selfish interests. The novel is a critical commentary on the destructive power of unchecked ambition and the pitfalls of vanity.

    The 589th Greatest Book of All Time
  8. 8. Death Of A Salesman by Arthur Miller

    This classic play explores the life of a failing salesman who, in his quest for the American Dream, struggles with his relationships and his own sense of reality. The protagonist's life spirals into despair as he grapples with his unfulfilled ambitions, strained family dynamics, and ultimately, his own mortality. The narrative delves deep into the themes of identity, illusion, and the destructive nature of the American Dream.

    The 825th Greatest Book of All Time
  9. 9. Cheese by Willem Elsschot

    A Business Novel

    The novel revolves around a Dutchman living in Antwerp, Belgium, who is persuaded by his brother to enter the cheese business. He invests in 10,000 full-cream cheeses and sets up an office, but struggles to sell any of his stock. As he grapples with the nuances of the cheese trade, his personal life and professional relationships also begin to crumble, leading to a series of comical and tragic events. The book is a satirical commentary on business, ambition, and the absurdity of life.

    The 964th Greatest Book of All Time
  10. 10. The Wapshot Chronicle by John Cheever

    "The Wapshot Chronicle" is a novel that explores the lives of the eccentric Wapshot family, who live in a quaint New England village. The story primarily focuses on the experiences of Leander Wapshot, the patriarch, and his two sons, Moses and Coverly, as they navigate through life's challenges. While Leander grapples with his advancing age and nostalgia, his sons are sent to find their own paths, dealing with their sexual identities, love, and their place in the world. This narrative is a blend of humor, tragedy, and family dynamics, showcasing the complexities of life and human nature.

    The 1329th Greatest Book of All Time
  11. 11. The Fortunes Of Richard Mahony by Henry Handel Richardson

    Australia Felix

    "The Fortunes of Richard Mahony" is a trilogy that chronicles the life of an Irish-born man who emigrates to Australia during the gold rush of the 1850s. The narrative follows his journey, detailing his struggles with mental health, the challenges of marriage, and the difficulties of raising a family in a foreign land. The story provides a deep insight into the complexities of human nature, the societal norms of the time, and the challenges faced by immigrants.

    The 1345th Greatest Book of All Time
  12. 12. Concrete by Thomas Bernhard

    The book is a darkly introspective narrative that delves into the mind of a reclusive, obsessive intellectual who is struggling to complete his scholarly work on the composer Mendelssohn. As he grapples with his own ailments and the perceived mediocrity of his surroundings, the protagonist's stream-of-consciousness monologue reveals his deep-seated anxieties, self-loathing, and profound isolation. The narrative is a relentless examination of the protagonist's psyche, showcasing his critical view of society and his own personal relationships, which are fraught with tension and dysfunction. Through this, the novel explores themes of artistic creation, intellectual elitism, and the suffocating nature of expectations and familial obligations.

    The 1675th Greatest Book of All Time
  13. 13. Spoon River Anthology by Edgar Lee Masters

    "Spoon River Anthology" is a collection of short free-form poems that tell the epitaphs of the residents of a fictional small town, Spoon River, which is modeled after the small towns of the author's youth. The poems reveal the honest, often harsh realities of life, as each deceased citizen tells their own tale of love, despair, success, failure, and the human condition. The book is a commentary on the hypocrisy, moral corruption, and societal constraints of early 20th century rural America.

    The 3763rd Greatest Book of All Time
  14. 14. Uncle Petros and Goldbach's Conjecture by Apostolos Doxiadis

    A Novel of Mathematical Obsession

    The novel follows the story of a young man who becomes fascinated by his reclusive and eccentric Uncle Petros. As he delves into his uncle's past, he uncovers Petros' obsession with proving Goldbach's Conjecture, a famous unsolved problem in number theory. This obsession led to Petros' alienation from society and ultimately his downfall. The book explores themes of mathematical obsession, family relationships, and the fine line between genius and madness.

    The 4026th Greatest Book of All Time
  15. 15. Home Land by Sam Lipsyte

    The novel is a darkly humorous account of a man named Lewis Miner, aka "Teabag," who is living a less-than-successful life. Lewis, who is in his thirties, writes hilariously bitter and sarcastic updates to his high school alumni newsletter, detailing his various failures in love, work, and life in general. The book is a biting satire of American life and the concept of success, filled with black humor and sharp, witty writing.

    The 4211th Greatest Book of All Time
  16. 16. The Emperor's Children by Claire Messud

    This novel follows the lives of three friends in their thirties living in New York City in the months leading up to and following the September 11 attacks. All children of privilege, they struggle with their careers, love lives, and identities against the backdrop of a changing world. The narrative explores themes of entitlement, disillusionment, and the often complicated nature of adult friendships.

    The 4250th Greatest Book of All Time
  17. 17. The Complete Works of Nathanael West by Nathanael West

    This collection features the complete works of a renowned American author, known for his dark humor and social criticism. The book includes four novels and various other writings that depict the disillusionment and despair of the Great Depression era. His stories often revolve around aspiring artists and Hollywood dreamers, exploring themes of fame, illusion, and the American Dream. The author's unique style blends satire and tragedy, creating a distinct voice in 20th-century American literature.

    The 4409th Greatest Book of All Time
  18. 18. The Art of Fielding by Chad Harbach

    "The Art of Fielding" is a tale centered around a college baseball star who seems destined for the big leagues but abruptly loses his ability to throw accurately. The story explores the aftermath of his downfall, the impact on his relationships with his teammates, roommates, and a college president, and the struggle of self-discovery and acceptance. It's a tale of friendship, ambition, and the pressures of expectation, all set against the backdrop of America's beloved pastime.

    The 4437th Greatest Book of All Time
  19. 19. The Pat Hobby Stories by F. Scott Fitzgerald

    This collection of short stories revolves around the character Pat Hobby, a down-and-out screenwriter in Hollywood during the 1930s. Once successful during the silent film era, Hobby struggles to adapt to the changing landscape of the film industry and to find work in the talkies era. The stories humorously and sometimes poignantly depict his various misadventures, schemes, and attempts to regain his lost prestige within the studio system. Through Hobby's experiences, the narrative offers a satirical glimpse into the Hollywood film industry, highlighting the fickleness of fame and the desperation that often accompanies creative endeavors.

    The 4595th Greatest Book of All Time
  20. 20. Rich Man, Poor Man by Irwin Shaw

    The novel chronicles the divergent paths of two brothers from a working-class family over several decades, starting in the years following World War II. The elder brother amasses wealth and power by building a successful business empire, embodying the American Dream, while the younger brother struggles with personal demons and a life of hardship, often living on the fringes of society. Their contrasting fortunes and the choices they make shape not only their own destinies but also the lives of those around them, painting a complex portrait of family dynamics, ambition, and the pursuit of success in mid-20th century America.

    The 5145th Greatest Book of All Time
  21. 21. Broken Glass by Alain Mabanckou

    "Broken Glass" is a satirical novel that takes place in a seedy bar in the Congo. The narrator, a disgraced schoolteacher known as Broken Glass, has been commissioned by the bar's owner to write about the bar and its regulars. The story is a chaotic, humorous, and poignant exploration of the lives of these characters, their histories, and their relationships, all told in a single, run-on sentence without any full stops.

    The 5610th Greatest Book of All Time
  22. 22. The Information by Martin Amis

    This book delves into the complexities of friendship, rivalry, and the pursuit of success within the literary world. It centers around two friends, one who has achieved fame and fortune as a novelist and the other who struggles with his own writing career, feeling overshadowed and envious. The narrative explores the darker sides of ambition, betrayal, and the quest for recognition, weaving a tale that examines the personal and professional dynamics between the two men. As the story unfolds, it reveals the lengths to which the struggling writer will go to reclaim a sense of self-worth and success, setting the stage for a compelling exploration of the human psyche and the often tumultuous world of literary fame.

    The 5966th Greatest Book of All Time
  23. 23. A Hologram For The King by Dave Eggers

    "A Hologram For The King" by Dave Eggers follows the story of Alan Clay, a washed-up salesman who is sent to Saudi Arabia to pitch a holographic teleconferencing system to the king. Struggling with personal and professional setbacks, Alan navigates cultural differences and the challenges of doing business in a foreign country while also reflecting on his own life and regrets. Along the way, he forms unexpected connections with the locals and learns valuable lessons about the meaning of success and the importance of human connection.

    The 7007th Greatest Book of All Time
  24. 24. Small Fry by Lisa Brennan-Jobs

    A Memoir

    "Small Fry" is a memoir by Lisa Brennan-Jobs, the daughter of Apple co-founder Steve Jobs. The book details her complicated relationship with her father, who denied paternity for several years before finally acknowledging her as his daughter. Brennan-Jobs describes the emotional abuse she endured at the hands of her father, who alternated between neglect and intense attention. The memoir also explores her own journey towards self-acceptance and forgiveness, as she grapples with the legacy of her famous and flawed parent.

    The 7119th Greatest Book of All Time
  25. 25. Raymond Carver by Carol Sklenicka

    A Writer's Life

    "Raymond Carver: A Writer’s Life" is a comprehensive biography of the renowned American short story writer. The book follows Carver's life from his childhood in rural Oregon to his rise to literary fame in the 1980s. Sklenicka delves into Carver's personal struggles with alcoholism and his complicated relationships with his family, friends, and fellow writers. She also examines his writing process and the evolution of his style. Through extensive research and interviews with those closest to Carver, Sklenicka paints a vivid portrait of a complex and influential writer.

    The 7119th Greatest Book of All Time

Reading Statistics

Click the button below to see how many of these books you've read!

Download

If you're interested in downloading this list as a CSV file for use in a spreadsheet application, you can easily do so by clicking the button below. Please note that to ensure a manageable file size and faster download, the CSV will include details for only the first 500 books.

Download