The Greatest American "Postmodern, Dark Humor" Books of All Time

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This list represents a comprehensive and trusted collection of the greatest books. Developed through a specialized algorithm, it brings together 305 '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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Postmodern

Postmodernism is a literary movement that emerged in the mid-20th century, characterized by a rejection of traditional narrative structures and a focus on self-reflexivity and intertextuality. Postmodern literature often features fragmented narratives, unreliable narrators, and a blurring of the lines between reality and fiction. It is a genre that challenges the notion of a single, objective truth and instead embraces the idea of multiple perspectives and interpretations. Postmodern literature is often seen as a response to the modernist movement that preceded it, and it continues to be a popular and influential category for contemporary writers.

Dark Humor

Dark humor is a genre of literature that combines humor with themes and subjects that are typically considered taboo, morbid, or controversial. It often involves making light of serious or disturbing topics such as death, violence, and mental illness. Dark humor can be used to satirize societal norms and conventions, challenge the status quo, and provide a unique perspective on the human condition. Books in this category may be unsettling or uncomfortable to read, but they offer a unique and often thought-provoking perspective on the world around us.

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  1. 1. Catch-22 by Joseph Heller

    The book is a satirical critique of military bureaucracy and the illogical nature of war, set during World War II. The story follows a U.S. Army Air Forces B-25 bombardier stationed in Italy, who is trying to maintain his sanity while fulfilling his service requirements so that he can go home. The novel explores the absurdity of war and military life through the experiences of the protagonist, who discovers that a bureaucratic rule, the "Catch-22", makes it impossible for him to escape his dangerous situation. The more he tries to avoid his military assignments, the deeper he gets sucked into the irrational world of military rule.

    The 18th Greatest Book of All Time
  2. 2. Infinite Jest by David Foster Wallace

    This novel is a complex, multi-layered narrative that explores themes of addiction, recovery, and the human condition in a near-future society. The story is set in a tennis academy and a halfway house for recovering addicts, and it intertwines the lives of its numerous characters, including a gifted but troubled teenage tennis prodigy, his filmmaker father, and a group of Quebecois separatists. The book is known for its length, intricate plot, and extensive use of footnotes.

    The 303rd Greatest Book of All Time
  3. 3. Wise Blood by Flannery O'Connor

    "Wise Blood" is a novel about a young man named Hazel Motes, who returns home to Tennessee after serving in World War II and finds his religious beliefs shaken. He becomes a street preacher, founding the Church Without Christ to preach his message of faithlessness. The book explores themes of redemption, faith, and the struggle between belief and atheism as Hazel interacts with a variety of eccentric characters and faces his own internal battles.

    The 485th Greatest Book of All Time
  4. 4. Cat's Cradle by Kurt Vonnegut

    This novel is a satirical commentary on modern man and his madness, exploring issues of science, technology, and religion. The story revolves around a narrator who becomes involved with the children of a deceased scientist, who had developed a substance capable of freezing water at room temperature. This substance, if misused, has the potential to end all life on earth. The novel is filled with strange and twisted characters, and culminates in a cataclysmic event, highlighting the dangers of uncontrolled technological advancement.

    The 506th Greatest Book of All Time
  5. 5. The Breakfast of Champions by Kurt Vonnegut

    The novel is a satirical depiction of American society, with a particular focus on its materialism, business culture, and obsession with success. It tells the story of two men: Dwayne Hoover, a wealthy businessman who is gradually losing his sanity, and Kilgore Trout, a largely unsuccessful science fiction writer. Their lives intersect in a series of absurd, tragicomic events, leading to a climax that forces the reader to question the nature of free will and the meaning of life. The narrative is punctuated by the author's own illustrations and frequent digressions on a wide range of topics.

    The 507th Greatest Book of All Time
  6. 6. Suttree by Cormac McCarthy

    Set in 1950s Knoxville, Tennessee, the novel follows the life of a man who has renounced his former existence of privilege to live among society's outcasts on the river. He is an educated man, who has chosen a life of fishing and surviving on the fringes of society. The narrative is filled with his encounters with various characters from the underbelly of the city, including criminals, prostitutes, and other outcasts. Despite his attempts to isolate himself, he finds himself drawn into the problems and tragedies of those around him.

    The 760th Greatest Book of All Time
  7. 7. Lincoln in the Bardo by George Saunders

    The novel is set in a graveyard over the course of a single night and is narrated by a dazzling chorus of voices. The story is centered around the death of President Lincoln's 11-year-old son Willie, who resides in the Bardo, a transitional state between life and rebirth in Tibetan tradition. As Willie interacts with the other spirits stuck in this realm, his father visits the crypt to mourn, causing a struggle among the ghosts over the boy's soul. The narrative explores themes of grief, the impermanence of life, and the unresolved issues that keep us from moving on.

    The 1585th Greatest Book of All Time
  8. 8. The Living End by Stanley Elkin

    "The Living End" is a darkly comedic and surreal exploration of the afterlife, where the protagonist, a liquor store owner, finds himself navigating the absurdities and injustices of heaven and hell following a violent robbery that leads to his untimely death. The narrative delves into themes of divine justice, eternal punishment, and the whims of a capricious God, as the protagonist encounters a cast of bizarre characters and experiences the ultimate existential crisis. Through sharp wit and biting satire, the story critiques religious conventions and the human quest for meaning in the face of an often indifferent universe.

    The 3011th Greatest Book of All Time
  9. 9. Going Native by Stephen Wright

    "Going Native" is a darkly surreal journey through the underbelly of late 20th-century American life. The protagonist, a seemingly ordinary suburban man, abandons his life to embark on a disturbing cross-country odyssey. The narrative unfolds through a series of interconnected vignettes, each exploring a different aspect of American society from the perspective of various eccentric and often dangerous characters. The novel is a disturbing exploration of identity, alienation, and the dark side of the American dream.

    The 5417th Greatest Book of All Time
  10. 10. Take It Or Leave It by Raymond Federman

    "Take It Or Leave It" is a unique narrative that blends fiction and autobiography. The story is about a French-American man who is drafted into the U.S. Army during the Korean War. The narrative is non-linear and fragmented, often digressing into side stories and anecdotes. The protagonist shares his experiences of growing up in France during World War II, his immigration to the United States, and his experiences in the army. The book plays with the conventions of storytelling and is known for its postmodern style.

    The 5732nd Greatest Book of All Time
  11. 11. Ray by Barry Hannah

    "Ray" is a darkly comedic and deeply moving novel about a Vietnam War veteran and former pilot who is grappling with his past and his own self-destructive tendencies. The protagonist's candid, often rambling monologues reveal his struggles with alcoholism, his failed marriages, and his complicated relationships with women, as well as his reflections on life, death, and the human condition. Set in the American South, the novel is a raw and poignant exploration of a flawed man's search for meaning and redemption.

    The 6379th Greatest Book of All Time
  12. 12. Chronic City by Jonathan Lethem

    "Chronic City" is a novel by Jonathan Lethem that follows the life of Chase Insteadman, a former child actor who has become a socialite in Manhattan. The story takes place in a surreal version of New York City where a mysterious fog has settled over the city and strange events occur. Along with a cast of eccentric characters, including a cultural critic, a reclusive author, and a giant tiger, Chase navigates the complexities of love, friendship, and the meaning of reality in a world that seems to be constantly shifting.

    The 7925th Greatest Book of All Time
  13. 13. Memories Of My Father Watching Tv by Curtis White

    The book presents a unique blend of autobiography and cultural criticism, exploring the impact of television on the American psyche through the lens of personal experience. It delves into the author's childhood memories of watching TV with his father, using this intimate framework to critique the medium's role in shaping family dynamics, politics, and social values. The narrative weaves together anecdotes and analysis, offering a poignant reflection on the pervasive influence of television and its power to mold our perceptions of reality, history, and identity.

    The 8139th Greatest Book of All Time
  14. 14. Something Happened by Joseph Heller

    In "Something Happened," the narrative delves into the mind of Bob Slocum, a successful yet disillusioned corporate executive navigating the complexities of his personal and professional life in post-war America. The novel, characterized by its stream-of-consciousness style, explores themes of anxiety, isolation, and the mundane horrors of everyday existence as Slocum grapples with his relationships with his family, his colleagues, and himself. Through a series of introspective and often disjointed reflections, the protagonist reveals his deep-seated fears and desires, painting a stark and unsettling portrait of a man overwhelmed by the banalities and moral ambiguities of American middle-class life.

    The 8730th Greatest Book of All Time

Reading Statistics

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