The Greatest Books of All Time on Guilt

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This list represents a comprehensive and trusted collection of the greatest books. Developed through a specialized algorithm, it brings together 366 '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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  1. 1. Lolita by Vladimir Nabokov

    or, The Confession of a White Widowed Male

    The novel tells the story of Humbert Humbert, a man with a disturbing obsession for young girls, or "nymphets" as he calls them. His obsession leads him to engage in a manipulative and destructive relationship with his 12-year-old stepdaughter, Lolita. The narrative is a controversial exploration of manipulation, obsession, and unreliable narration, as Humbert attempts to justify his actions and feelings throughout the story.

    The 6th Greatest Book of All Time
  2. 2. Crime and Punishment by Fyodor Dostoevsky

    A young, impoverished former student in Saint Petersburg, Russia, formulates a plan to kill an unscrupulous pawnbroker to redistribute her wealth among the needy. However, after carrying out the act, he is consumed by guilt and paranoia, leading to a psychological battle within himself. As he grapples with his actions, he also navigates complex relationships with a variety of characters, including a virtuous prostitute, his sister, and a relentless detective. The narrative explores themes of morality, redemption, and the psychological impacts of crime.

    The 13th Greatest Book of All Time
  3. 3. The Sound and the Fury by William Faulkner

    The novel is a complex exploration of the tragic Compson family from the American South. Told from four distinct perspectives, the story unfolds through stream of consciousness narratives, each revealing their own understanding of the family's decline. The characters grapple with post-Civil War societal changes, personal loss, and their own mental instability. The narrative is marked by themes of time, innocence, and the burdens of the past.

    The 19th Greatest Book of All Time
  4. 4. The Brothers Karamazov by Fyodor Dostoevsky

    A Novel in Four Parts With Epilogue

    This classic novel explores the complex, passionate, and troubled relationship between four brothers and their father in 19th century Russia. The narrative delves into the themes of faith, doubt, morality, and redemption, as each brother grapples with personal dilemmas and family conflicts. The story culminates in a dramatic trial following a murder, which serves as a microcosm of the moral and philosophical struggles faced by each character, and by extension, humanity itself.

    The 21st Greatest Book of All Time
  5. 5. Great Expectations by Charles Dickens

    A young orphan boy, living with his cruel older sister and her kind blacksmith husband, has an encounter with an escaped convict that changes his life. Later, he becomes the protégé of a wealthy but reclusive woman and falls in love with her adopted daughter. He then learns that an anonymous benefactor has left him a fortune, leading him to believe that his benefactor is the reclusive woman and that she intends for him to marry her adopted daughter. He moves to London to become a gentleman, but his great expectations are ultimately shattered when he learns the true identity of his benefactor and the reality of his love interest.

    The 30th Greatest Book of All Time
  6. 6. The Trial by Franz Kafka

    The book revolves around a bank clerk who wakes one morning to find himself under arrest for an unspecified crime. Despite not being detained, he is subjected to the psychological torment of a bizarre and nightmarish judicial process. The story is a critique of bureaucracy, exploring themes of guilt, alienation and the inefficiency of the justice system.

    The 31st Greatest Book of All Time
  7. 7. Frankenstein by Mary Shelley

    The Modern Prometheus

    This classic novel tells the story of a young scientist who creates a grotesque but sentient creature in an unorthodox scientific experiment. The scientist, horrified by his creation, abandons it, leading the creature to seek revenge. The novel explores themes of ambition, responsibility, guilt, and the potential consequences of playing God.

    The 38th Greatest Book of All Time
  8. 8. Absalom, Absalom! by William Faulkner

    This novel is a complex narrative about Thomas Sutpen, a poor white man who rises to power in the South, aiming to create a dynasty that would rival the old aristocratic families. However, his ambitions are thwarted by his own flawed decisions and the overarching racial and societal tensions of the era. The story is not told in a linear fashion but rather through a series of interconnected flashbacks and narratives, offering different perspectives on the same events. The book explores themes of family, class, race, and the destructive power of obsession.

    The 45th Greatest Book of All Time
  9. 9. Beloved by Toni Morrison

    This novel tells the story of a former African-American slave woman who, after escaping to Ohio, is haunted by the ghost of her deceased daughter. The protagonist is forced to confront her repressed memories and the horrific realities of her past, including the desperate act she committed to protect her children from a life of slavery. The narrative is a poignant exploration of the physical, emotional, and psychological scars inflicted by the institution of slavery, and the struggle for identity and self-acceptance in its aftermath.

    The 47th Greatest Book of All Time
  10. 10. Rebecca by Daphne du Maurier

    A young woman marries a wealthy widower and moves into his large English country house. She quickly realizes that the memory of her husband's first wife, Rebecca, haunts every corner of the estate. The housekeeper's obsessive devotion to Rebecca and the mysterious circumstances of her death continue to overshadow the second wife's attempts to make a happy life with her husband. As secrets about Rebecca's life and death are revealed, the new wife must grapple with her own identity and place within the household.

    The 70th Greatest Book of All Time
  11. 11. Faust by Johann Wolfgang von Goethe

    A Tragedy

    The book is a tragic play in two parts that tells the story of a scholarly man named Faust, who becomes dissatisfied with his life and makes a pact with the devil, Mephistopheles. In exchange for unlimited knowledge and worldly pleasures, Faust agrees to give his soul to Mephistopheles after death. The narrative explores themes of ambition, despair, love, and redemption, ultimately leading to Faust's salvation.

    The 74th Greatest Book of All Time
  12. 12. Oedipus the King by Sophocles

    "Oedipus the King" is a tragic play that revolves around the life of Oedipus, the king of Thebes, who is prophesied to kill his father and marry his mother. Despite his attempts to avoid this fate, Oedipus unknowingly fulfills the prophecy. When he discovers the truth about his actions, he blinds himself in despair. The play explores themes of fate, free will, and the quest for truth, highlighting the tragic consequences of human hubris and ignorance.

    The 75th Greatest Book of All Time
  13. 13. The Stories of Anton Chekhov by Anton Chekhov

    This collection of short stories explores the complexities of human nature and society in 19th-century Russia. Written by a renowned Russian author, the stories range from humorous to tragic, often focusing on the everyday lives and struggles of ordinary people. The author's keen observation and deep understanding of human nature shine through in these tales, making them timeless classics that continue to resonate with readers today.

    The 77th Greatest Book of All Time
  14. 14. The Metamorphosis by Franz Kafka

    The book tells the story of a man who wakes up one morning to find himself transformed into a giant insect. His transformation causes him to lose his job and become ostracized from his family, who are horrified and repulsed by his new form. As he grapples with his new reality, he becomes increasingly isolated and starts to lose his sense of humanity. The book explores themes of alienation, guilt, and identity, and is a profound examination of the human condition.

    The 82nd Greatest Book of All Time
  15. 15. The Picture of Dorian Gray by Oscar Wilde

    The novel follows the life of a handsome young man who, after having his portrait painted, is upset to realize that the painting will remain beautiful while he ages. After expressing a wish that the painting would age instead of him, he is shocked to find that his wish comes true. As he indulges in a life of hedonism and immoral acts, his portrait becomes increasingly grotesque, reflecting the damage his actions have on his soul. The story serves as a cautionary tale about the dangers of vanity, selfishness, and the pursuit of pleasure without regard for consequences.

    The 83rd Greatest Book of All Time
  16. 16. A Portrait of the Artist as a Young Man by James Joyce

    This novel is a semi-autobiographical account of a young man's intellectual and artistic development in late 19th-century Ireland. The protagonist struggles with issues of identity, faith, and nationality, ultimately rejecting the traditional values of his Catholic upbringing to pursue his own path as an artist. The book is renowned for its innovative narrative style and its exploration of themes such as individuality, freedom, and the nature of art.

    The 90th Greatest Book of All Time
  17. 17. The Scarlet Letter by Nathaniel Hawthorne

    A Romance

    Set in 17th-century Puritan Boston, this novel tells the story of a woman who conceives a daughter through an affair and struggles to create a new life of repentance and dignity. She is forced to wear a scarlet "A" on her dress as a sign of her adultery while her lover, a revered local minister, remains unnamed and unpunished. Throughout the book, themes of sin, legalism, and guilt are explored.

    The 92nd Greatest Book of All Time
  18. 18. The Complete Tales and Poems of Edgar Allan Poe by Edgar Allan Poe

    This collection brings together all of the author's most famous works, including poems, short stories, and novellas. Known for his macabre and gothic storytelling, the author's works are filled with themes of death, love lost, and human frailty. Notable inclusions are the haunting poem "The Raven," the chilling stories "The Tell-Tale Heart" and "The Fall of the House of Usher," and his only complete novel, "The Narrative of Arthur Gordon Pym."

    The 100th Greatest Book of All Time
  19. 19. Under the Volcano by Malcolm Lowry

    Set in Mexico on the Day of the Dead in 1938, the novel follows the last day in the life of Geoffrey Firmin, a British consul with a severe alcohol addiction. Through his interactions with his estranged wife and half-brother, the book explores themes of despair, betrayal, and the destructive power of addiction, against the backdrop of political and social unrest. The impending eruption of the nearby volcano serves as a metaphor for Firmin's deteriorating mental state and the looming world war.

    The 104th Greatest Book of All Time
  20. 20. Tess of the d'Urbervilles by Thomas Hardy

    A Pure Woman Faithfully Presented

    This is a tragic tale of a young woman named Tess who comes from a poor family in rural England. Tess is sent to work for a wealthy family, where she is seduced by a man who abandons her after she becomes pregnant. The baby dies, and Tess is ostracized by her community. She falls in love with a kind man, but when she confesses her past, he rejects her. Desperate and heartbroken, Tess murders her former seducer and is eventually captured and executed. The novel explores themes of fate, injustice, and the oppressive sexual morals of its time.

    The 108th Greatest Book of All Time
  21. 21. Native Son by Richard Wright

    This novel tells the story of Bigger Thomas, a young African-American man living in Chicago's South Side during the 1930s. Bigger's life takes a tragic turn when he accidentally kills a young white woman. The incident leads to his arrest and trial, revealing the deep-seated racial prejudices and injustices prevalent in American society at the time. The narrative explores themes of poverty, systemic racism, fear, and the effects of oppression.

    The 112th Greatest Book of All Time
  22. 22. Lord Jim by Joseph Conrad

    A Tale

    The novel revolves around a young, idealistic British seaman, who commits a crime of cowardice at sea. He abandons his ship, leaving hundreds of passengers to their fate. He is publicly censured for this act and spends the rest of his life in shameful obscurity in the South Seas, trying to repress the guilt of his past and regain his lost honor. His quest for redemption leads him to a remote island where he gets a chance to prove his courage, but his tragic flaw ultimately leads to his downfall.

    The 128th Greatest Book of All Time
  23. 23. Pedro Páramo by Juan Rulfo

    This novel transports readers to the ghost town of Comala, where the protagonist, Juan Preciado, ventures in search of his estranged father, Pedro Páramo. Upon arrival, he encounters a realm where the living and the dead coexist, and through fragmented narratives and spectral encounters, the story of Pedro Páramo's life, his love, tyranny, and the curses that plague the town unfolds. The novel's innovative structure, blending memory and reality, has cemented its status as a pioneering work of magical realism, offering a haunting exploration of power, guilt, and the inescapable echoes of the past.

    The 141st Greatest Book of All Time
  24. 24. Macbeth by William Shakespeare

    This classic play follows the tragic tale of Macbeth, a Scottish general whose ambition is sparked by a prophecy from three witches that he will one day become King of Scotland. Consumed by ambition and spurred on by his wife, Macbeth murders King Duncan and takes the throne. However, guilt and paranoia plague him, leading to a reign of terror and further bloodshed. His desperate attempts to cling onto power lead to his downfall, illustrating the destructive power of unchecked ambition.

    The 147th Greatest Book of All Time
  25. 25. First Folio by William Shakespeare

    Mr. William Shakespeares Comedies, Histories, & Tragedies

    This collection is a compilation of 36 plays by a renowned English playwright, published seven years after his death. It includes comedies, histories, and tragedies, some of which had never been published before. Notable works in the compilation include "Macbeth," "Julius Caesar," "Twelfth Night," "The Tempest," and "As You Like It." The collection is considered one of the most influential books ever published in the English language, as it preserved many of the playwright's works that might have otherwise been lost.

    The 156th Greatest Book of All Time

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