The Greatest Books of All Time on Sexuality

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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. Ulysses by James Joyce

    Set in Dublin, the novel follows a day in the life of Leopold Bloom, an advertising salesman, as he navigates the city. The narrative, heavily influenced by Homer's Odyssey, explores themes of identity, heroism, and the complexities of everyday life. It is renowned for its stream-of-consciousness style and complex structure, making it a challenging but rewarding read.

    The 2nd Greatest Book of All Time
  2. 2. Leaves of Grass by Walt Whitman

    A Collection of Poems

    "Leaves of Grass" is a collection of poetry that celebrates the human form and condition, while also exploring themes of democracy, nature, love, and friendship. The book, known for its departure from traditional poetic form, features a free verse style and the use of everyday language. The poet presents himself as both an individual and a universal figure, representing the collective American experience and identity. The collection is also notable for its controversial content at the time of its publication, including candid depictions of sexuality.

    The 67th Greatest Book of All Time
  3. 3. The Golden Notebook by Doris May Lessing

    The novel centers around a woman named Anna Wulf, a writer who keeps four notebooks, each representing a different aspect of her life: her experiences in Africa, her current life in London, a novel she is writing, and her personal experiences. As Anna's mental state deteriorates, she attempts to unify her fragmented self in a fifth notebook, the golden notebook. The novel explores themes of mental breakdown, communism, the changing role of women, and the fear of nuclear war.

    The 85th Greatest Book of All Time
  4. 4. 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
  5. 5. The Second Sex by Simone de Beauvoir

    This influential work explores the treatment and perception of women throughout history, arguing that women have been repressed and defined only in relation to men. The author presents a detailed analysis of women's roles in society, family, work, and in the creation of their own identities. She discusses the concept of 'the other' and how this has been used to suppress women, while also examining the biological, psychological, and societal impacts of this oppression. The book is a seminal text in feminist theory, challenging traditional notions of femininity and calling for equality and freedom for women.

    The 107th Greatest Book of All Time
  6. 6. The Unbearable Lightness of Being by Milan Kundera

    Set against the backdrop of the Prague Spring period of Czechoslovak history, the novel explores the philosophical concept of Nietzsche's eternal return through the intertwined lives of four characters: a womanizing surgeon, his intellectual wife, his naïve mistress, and her stoic lover. The narrative delves into their personal struggles with lightness and heaviness, freedom and fate, love and betrayal, and the complexities of human relationships, all while offering a profound meditation on the nature of existence and the paradoxes of life.

    The 131st Greatest Book of All Time
  7. 7. Sons and Lovers by D. H. Lawrence

    "Sons and Lovers" is a semi-autobiographical novel that explores the complex relationships between a miner's wife, her husband, and their two sons. The story focuses on the intense emotional and psychological bonds between the mother and her sons, as well as the struggles they face in their romantic relationships due to their deep attachment to their mother. The novel delves into themes of class, love, sexuality, and the oedipal complex, presenting a vivid picture of working-class life in early 20th century England.

    The 150th Greatest Book of All Time
  8. 8. Portnoy's Complaint by Philip Roth

    The novel is a first-person narrative, a monologue by a young Jewish man, Alexander Portnoy, who is speaking to his psychoanalyst. He shares his struggles with his identity as a Jewish man in America, his sexual fantasies and frustrations, his complex relationship with his overbearing mother, and his experiences of guilt and shame. The book uses humor and frank language to explore themes of identity, sexuality, and the Jewish experience in America.

    The 167th Greatest Book of All Time
  9. 9. The Waste Land by T. S. Eliot

    "The Waste Land" is a long poem that presents a bleak and despairing view of the world following the devastation of World War I. The poem is divided into five parts and uses a wide range of literary and cultural references, as well as multiple narrators, to depict a world in ruins. It explores themes of disillusionment, despair, and the decline of civilization, and is often considered a seminal work of modernist literature.

    The 169th Greatest Book of All Time
  10. 10. Lady Chatterley's Lover by D. H. Lawrence

    "Lady Chatterley's Lover" is a controversial novel that explores themes of class, sexuality, and the human condition. The story revolves around a young, upper-class woman married to a paralyzed war veteran who, feeling emotionally and physically neglected, embarks on a passionate affair with the estate's gamekeeper. The narrative delves into the protagonist's sexual awakening and her struggle against societal norms, ultimately advocating for emotional honesty and physical intimacy as essential components of a fulfilling life.

    The 178th Greatest Book of All Time
  11. 11. Giovanni's Room by James Baldwin

    The novel explores themes of identity, sexuality, and societal norms in mid-20th century Paris. The protagonist, an American man, grapples with his homosexual identity while engaged to a woman. His life takes a turn when he becomes involved with an Italian bartender, leading to a tumultuous relationship filled with passion, guilt, and self-loathing. The story is a poignant examination of the human struggle for acceptance and the destructive consequences of denying one's true self.

    The 180th Greatest Book of All Time
  12. 12. The World According to Garp by John Irving

    The novel follows the life of T.S. Garp, the illegitimate son of a feminist mother, who becomes a writer. Garp's life is filled with unusual experiences and characters, from his unconventional conception to his untimely death. He navigates through a world filled with sexual violence, infidelity, and gender issues, and his life story is punctuated by his own literary creations. His mother's feminist ideals and the tragic events of his life deeply influence his writing and worldview.

    The 224th Greatest Book of All Time
  13. 13. The Lover by Marguerite Duras

    "The Lover" is a poignant exploration of forbidden love, power dynamics, and colonialism. Set in 1930s French Indochina, it tells the story of a tumultuous and passionate affair between a 15-year-old French girl and her wealthy, older Chinese lover. The narrative delves into the complexities of their relationship, the societal norms they defy, and the inevitable heartbreak that follows. The protagonist's struggle with her family's poverty and her mother's mental instability further complicates the story, making it a compelling exploration of love, desire, and societal constraints.

    The 252nd Greatest Book of All Time
  14. 14. Women in Love by D. H. Lawrence

    "Women in Love" is a novel that explores the complex relationships of two sisters, Ursula and Gudrun Brangwen, as they navigate their passions, desires, and connections with two men, Rupert Birkin and Gerald Crich, in post-World War I England. The novel delves deep into the psychological aspects of love, questioning traditional romantic love and proposing a more modern, individualistic approach to relationships. It also explores themes of industrialization, modernity, and the nature of human existence.

    The 275th Greatest Book of All Time
  15. 15. The Alexandria Quartet by Lawrence Durrell

    "The Alexandria Quartet" is a tetralogy of novels that explore the intricate relationships between a group of friends and lovers in Alexandria, Egypt, before and during World War II. The novels are known for their rich and evocative descriptions of the city and its diverse inhabitants, as well as their innovative narrative structure, which presents the same events from different characters' perspectives in each book. The work explores themes of love, betrayal, and the nature of reality and perception.

    The 280th Greatest Book of All Time
  16. 16. Finnegans Wake by James Joyce

    This complex and challenging novel is renowned for its experimental style and intricate, dreamlike narrative. It explores the story of a publican in Dublin, his wife, and their three children, but the plot is not linear and often veers into surreal and abstract territory. The book is dense with linguistic games, puns, and allusions to a myriad of cultural, historical, and mythological sources. The narrative is circular, ending in the middle of a sentence that is completed at the start of the book, embodying the cyclical nature of life and history.

    The 294th Greatest Book of All Time
  17. 17. Winesburg, Ohio by Sherwood Anderson

    A Group of Tales of Ohio Small-Town Life

    "Winesburg, Ohio" is a collection of interconnected short stories that paints a picture of life in a small town in the early 20th century. The book captures the hopes, dreams, and despair of the inhabitants of Winesburg, focusing on a young reporter as he interacts with the townspeople. Each character's story reveals their inner struggles, loneliness, and search for understanding and connection, providing a profound exploration of human nature and the complexities of life in a small community.

    The 313th Greatest Book of All Time
  18. 18. Middlesex by Jeffrey Eugenides

    The book follows the life of Calliope Stephanides, a Greek-American hermaphrodite, who narrates her epic story starting from her grandparents' incestuous relationship in a small village in Asia Minor to her own self-discovery in 20th century America. The novel delves into themes of identity, gender, and the American dream, while also providing a detailed history of Detroit through the eyes of three generations of an immigrant family.

    The 342nd Greatest Book of All Time
  19. 19. Another Country by James Baldwin

    "Another Country" is a profound exploration of racial, sexual, and creative issues in 1950s Manhattan. The story follows the lives of various characters, including a jazz drummer, a Southern white woman, and a black playwright, among others. As the narrative unfolds, it delves into their struggles with identity, prejudice, and interpersonal relationships, offering a raw and unflinching portrayal of America's social and cultural landscape during a time of intense change and conflict.

    The 360th Greatest Book of All Time
  20. 20. Nightwood by Djuna Barnes

    "Nightwood" is a modernist novel that explores the complex relationships and sexuality of a group of Americans and Europeans living in Paris in the 1920s. The story primarily revolves around the tumultuous love affair between two women, one of whom is a married aristocrat. The narrative, known for its poetic and dense language, delves deep into the characters' psyches, exploring themes of identity, gender, and desire. The novel is also notable for its frank and groundbreaking depiction of homosexuality and transgender issues.

    The 362nd Greatest Book of All Time
  21. 21. Season of Migration to the North by Al-Tayyib Salih

    The novel is a post-colonial exploration of the complex relationship between the East and the West. It tells the story of a young man who returns to his village in Sudan after studying in Europe, only to find that a new villager, a man who has also spent time in the West, has brought back with him a very different perspective on the relationship between the two cultures. The story unfolds as a gripping psychological drama, filled with themes of identity, alienation, and the clash of cultures.

    The 380th Greatest Book of All Time
  22. 22. Stranger in a Strange Land by Robert A. Heinlein

    The novel follows the life of Valentine Michael Smith, a human who was raised on Mars and returns to Earth in early adulthood. Smith struggles to understand human culture, norms, and conventions, while also possessing extraordinary psychic abilities. As he navigates Earth society, he begins to question many of its institutions and values, ultimately creating his own religion to pass on the wisdom he gained on Mars. The book explores themes of freedom, self-reliance, and the nature of humanity, and is considered a classic of science fiction literature.

    The 381st Greatest Book of All Time
  23. 23. Ada or Ardor by Vladimir Nabokov

    A Family Chronicle

    Set in an alternate universe where Earth is known as "Antiterra," the novel follows the lives of Ada and Van, two wealthy siblings who fall into a passionate and incestuous love affair. Their relationship evolves over a span of 70 years, as they navigate through family secrets, personal tragedies, and the complex nature of time. The book is a blend of romance, science fiction, and philosophical exploration, all told through the author's signature wordplay and intricate narrative style.

    The 403rd Greatest Book of All Time
  24. 24. Rabbit Is Rich by John Updike

    The book follows the life of a former high school basketball star, who is now in his mid-forties and has inherited a Toyota dealership from his father-in-law. He is living a comfortable life with his wife and son in Brewer, Pennsylvania during the late 1970s. The story unfolds as he navigates through his midlife crisis, dealing with his rebellious son, his longing for his old mistress, and his own insecurities and dissatisfaction. The narrative provides a deep dive into the protagonist's thoughts and feelings, offering a detailed examination of middle-class American life during this era.

    The 545th Greatest Book of All Time
  25. 25. Crash by J. G. Ballard

    The novel revolves around a man who becomes sexually aroused by staging and participating in real car-crashes, a fetish that spirals further out of control when he meets a like-minded woman. It explores the disturbing intersection of technology, sexuality, and violence, pushing the boundaries of social norms and challenging the reader's perception of reality.

    The 569th Greatest Book of All Time

Reading Statistics

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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.

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