The Greatest "Dark Humor, Fiction" Books Since 1990

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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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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. 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
  2. 2. Trainspotting by Irvine Welsh

    This novel is a gritty, raw portrayal of a group of heroin addicts living in Edinburgh, Scotland. The narrative is non-linear and told from multiple perspectives, providing a deep dive into the minds and lives of these characters. The story explores themes of poverty, addiction, friendship, and the struggle to escape one's circumstances, all set against the backdrop of a bleak urban landscape. It is known for its strong Scottish dialect, graphic content, and dark humor.

    The 1099th Greatest Book of All Time
  3. 3. The Butcher Boy by Patrick McCabe

    The Butcher Boy is a dark and disturbing tale set in small-town Ireland, following the life of a troubled young boy who descends into madness and violence. The protagonist's life is filled with neglect, abuse and mental health issues, and his increasingly erratic behavior and gruesome fantasies lead him down a path of horrific actions. The novel provides a stark exploration of the effects of societal neglect and the failure of mental health systems.

    The 1115th Greatest Book of All Time
  4. 4. The Sellout by Paul Beatty

    This satirical novel follows the story of an African-American man living in a small, agrarian town on the outskirts of Los Angeles. After his father's death, he attempts to reinstate slavery and segregation in his town as a means of creating a sense of identity for himself and his community. The novel explores themes of racial identity and equality in America, challenging societal norms and expectations through its provocative narrative.

    The 1184th Greatest Book of All Time
  5. 5. How Late It Was, How Late by James Kelman

    The novel is a stream-of-consciousness narrative told from the perspective of Sammy, a shoplifter and ex-convict from Glasgow who wakes up in an alley after a two-day drinking binge to find he is completely blind. As Sammy struggles to navigate his new reality, he contends with bureaucratic systems, confronts his past, and grapples with his relationships, all while trying to understand and adjust to his sudden loss of sight. The story is a gritty exploration of working-class life, the human condition, and the nature of reality.

    The 1332nd Greatest Book of All Time
  6. 6. 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
  7. 7. Bad News by Edward St Aubyn

    "Bad News" is the second novel in a series that follows the life of Patrick Melrose, a man from a wealthy but deeply troubled family. In this installment, Patrick, now 22, must travel to New York to collect his father's ashes. As he navigates the city, he struggles with his addiction to drugs and alcohol, and grapples with the traumatic memories of his abusive father. The narrative provides a darkly comic and deeply poignant exploration of addiction, trauma, and the struggle for redemption.

    The 2145th Greatest Book of All Time
  8. 8. Some Hope by Edward St Aubyn

    "Some Hope" is a darkly humorous novel that delves into the life of a man who struggles to overcome his traumatic past and drug addiction. He is invited to a lavish party filled with Britain's aristocracy, where he must confront his past and deal with the pretentious and shallow society he is part of. The narrative explores themes of abuse, recovery, and the struggle to find redemption and hope amidst despair.

    The 2225th Greatest Book of All Time
  9. 9. Billy Lynn's Long Halftime Walk: A Novel by Ben Fountain

    The novel follows Billy Lynn, a 19-year-old soldier, who, along with his fellow soldiers in Bravo Squad, becomes a hero after a harrowing Iraq battle and is brought home temporarily for a victory tour. During the tour, they're honored at a Dallas Cowboys game, which exposes the commercialization and shallow appreciation of their sacrifices. Amidst the celebration, Billy grapples with his understanding of heroism, patriotism, family, and the stark contrast between the realities of war and America's perceptions.

    The 2385th Greatest Book of All Time
  10. 10. Pastoralia by George Saunders

    "Pastoralia" is a collection of six short stories, each delving into the world of weird, dystopian future and highlighting the author's satirical and surreal take on modern life. The stories are set in bizarre environments and situations, such as a couple working as cavemen in a theme park, a male stripper trying to help his mentally ill sister, and a corporate drone receiving cryptic messages from his boss. The characters in these stories struggle with their personal problems while navigating through the absurdity of their surroundings, showcasing the author's unique blend of humor, empathy, and social commentary.

    The 4088th Greatest Book of All Time
  11. 11. Vernon God Little by DBC Pierre

    The book revolves around the life of a 15-year-old boy, Vernon Little, living in a small town in Texas. After a horrific school shooting where his best friend kills 16 of their classmates before committing suicide, Vernon becomes the prime suspect. With the media and law enforcement on his tail, he attempts to escape to Mexico, resulting in a series of unfortunate events and dark comedic situations. The narrative is a biting satire of America's obsession with fame and the justice system.

    The 4821st Greatest Book of All Time
  12. 12. Do Everything in the Dark by Gary Indiana

    This book presents a disjointed narrative of a group of aging artists and intellectuals in New York City who are dealing with the aftermath of their youthful, hedonistic lives. As they grapple with issues of aging, depression, suicide, and the loss of their creative abilities, they find themselves trapped in a dark, cynical world, haunted by their pasts and facing an uncertain future. The novel offers a bleak but insightful look at the human condition, exploring themes of despair, regret, and the struggle to find meaning in life.

    The 5018th Greatest Book of All Time
  13. 13. The Moscoviad by Yuri Andrukhovych

    "The Moscoviad" is a satirical novel that follows the journey of a group of Ukrainian intellectuals as they embark on a chaotic and absurd trip to Moscow. Through a series of hilarious and bizarre encounters, the author explores the complex relationship between Ukraine and Russia, while also delving into the themes of identity, history, and cultural clashes. With its sharp wit and biting commentary, the novel offers a unique perspective on the post-Soviet era and the tensions between the two neighboring countries.

    The 5150th Greatest Book of All Time
  14. 14. My Year of Rest and Relaxation by Ottessa Moshfegh

    The novel follows the life of a young, beautiful, and wealthy woman living in New York City who decides to enter a year of drug-induced sleep to escape her disillusionment with life and the world around her. Encouraged by her eccentric, unethical psychiatrist, she spends most of her time sleeping, waking only to eat, watch movies, and occasionally socialize with her best friend. The book explores themes of depression, alienation, and the search for meaning in a modern, materialistic society.

    The 5308th Greatest Book of All Time
  15. 15. 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
  16. 16. CivilWarLand in Bad Decline by George Saunders

    This book is a collection of short stories and a novella, all set in dystopian versions of America. The narratives often feature theme parks, which serve as metaphors for the cultural and moral decay of society. The characters are often trapped in low-wage jobs and are struggling to make ends meet, while also grappling with various personal issues. The stories are infused with dark humor and satire, and they provide a critique of capitalism and consumer culture.

    The 5627th Greatest Book of All Time
  17. 17. How The Dead Live by Will Self

    This novel presents a unique and imaginative exploration of the afterlife, where the protagonist, a recently deceased middle-aged American woman, finds herself in a surreal version of London. In this otherworldly place, she is accompanied by a peculiar guide and is forced to confront the successes and failures of her life, her relationships with her family, and the impact of her choices. The narrative delves into themes of mortality, the meaning of existence, and the complexities of the human condition, all while maintaining a darkly comedic tone. Through its vividly imaginative setting and introspective journey, the story offers a thought-provoking look at what might lie beyond death, challenging readers to reflect on their own lives and the nature of the afterlife.

    The 6554th Greatest Book of All Time
  18. 18. My Sister, The Serial Killer by Oyinkan Braithwaite

    In this darkly comedic novel, a nurse named Korede finds herself repeatedly cleaning up after her sister Ayoola, who has a disturbing habit of killing her boyfriends. As Ayoola's murderous tendencies escalate, Korede is torn between her loyalty to her sister and her growing concern for the next potential victim. As secrets unravel and tensions rise, the sisters' bond is put to the ultimate test, leading to a gripping and unexpected conclusion.

    The 6710th Greatest Book of All Time
  19. 19. Cruddy by Lynda Barry

    In the darkly comic and unsettling novel, a teenage girl recounts her harrowing journey through a dysfunctional childhood marked by neglect, abuse, and a road trip with her dangerously unhinged father. As she navigates the grim realities of her life, her story oscillates between the grimy, violent past and her struggle to survive in the present. The narrative, rich with vivid and disturbing imagery, explores themes of memory, trauma, and the resilience of the human spirit in the face of overwhelming adversity. The protagonist's voice, both raw and poignant, offers a stark and unflinching look at the complexities of family and the scars that our early experiences can leave on us.

    The 7870th Greatest Book of All Time
  20. 20. 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
  21. 21. The Accidental by Ali Smith

    The novel centers around a woman named Amber who unexpectedly arrives and disrupts the lives of the Smart family while they are on summer holiday in Norfolk. Each family member - Eve, a writer, Michael, a university professor, and their children Astrid and Magnus - experience unique interactions with Amber, causing them to question their own realities. The mysterious woman's influence forces the family to confront their secrets, insecurities, and the false narratives they've created about themselves.

    The 8109th Greatest Book of All Time
  22. 22. 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
  23. 23. Haunted by Chuck Palahniuk

    "Haunted" is a novel composed of 23 stories, all told by people who have answered an ad for a writer's retreat. The individuals are locked inside a theater for three months, with no connection to the outside world. As time goes on, they begin to starve, go mad, and resort to violence. Each character's story reveals their darkest secrets and fears, creating a chilling and disturbing narrative.

    The 8505th Greatest Book of All Time
  24. 24. Mailman by J. Robert Lennon

    The novel centers around the life of a seemingly ordinary mail carrier in a small American town, whose mundane existence belies a complex inner world filled with secrets, fantasies, and obsessions. As the protagonist navigates his daily routine, delivering letters and packages to the townspeople, he becomes increasingly entangled in their lives and personal affairs. His voyeuristic tendencies and the discovery of a mysterious undeliverable letter lead to a series of events that unravel his carefully constructed facade, exposing the dark undercurrents of suburban life and the fragile nature of personal identity.

    The 8513th Greatest Book of All Time
  25. 25. John Dies At The End by David Wong

    This book is a comedic horror novel that follows two college dropouts who gain psychic abilities after ingesting a mysterious drug known as "Soy Sauce." This substance opens their eyes to a bizarre and terrifying parallel universe, leading them on a surreal adventure as they confront an array of supernatural creatures, ghosts, and otherworldly threats. With a blend of humor, philosophy, and horror, the narrative takes readers on a wild ride through existential crises and the nature of reality, all while the fate of humanity hangs in the balance.

    The 9099th 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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