The Greatest "Humor, Satire, New York" 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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Humor

Humor is a category of books that is characterized by its ability to make readers laugh or feel amused. These books often contain witty dialogue, clever wordplay, and humorous situations that are designed to entertain and delight readers. Humor can be found in a variety of genres, including fiction, non-fiction, memoirs, and graphic novels, and can range from light-hearted and silly to dark and satirical. Whether you're looking for a quick laugh or a more in-depth exploration of the human condition through humor, there is something for everyone in the world of humorous books.

Satire

Satire is a genre of literature that uses humor, irony, and exaggeration to criticize and ridicule human vices, follies, and shortcomings. It is a form of social commentary that aims to expose the flaws and absurdities of society, politics, and culture. Satirical books often employ sarcasm, wit, and parody to challenge the status quo and provoke thought and reflection in readers. Satire can be both entertaining and thought-provoking, and it has been used throughout history as a powerful tool for social and political critique.

New York

The "New York" category of books typically refers to literature that is set in or explores the city of New York. These books may focus on the city's history, culture, and landmarks, or they may delve into the lives of its diverse inhabitants. From gritty crime novels to romantic comedies, the "New York" category encompasses a wide range of genres and styles, all united by their connection to one of the world's most iconic cities. Whether you're a native New Yorker or a curious outsider, these books offer a unique glimpse into the heart of the Big Apple.

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  1. 1. 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 151st Greatest Book of All Time
  2. 2. The Amazing Adventures of Kavalier and Clay by Michael Chabon

    The book follows the lives of two Jewish cousins, one a skilled escape artist and the other a talented artist, before, during, and after World War II. They create a popular comic book superhero, which brings them fame and fortune. However, their success is complicated by personal struggles, including the escape artist's attempts to rescue his family from Nazi-occupied Prague and the artist's struggle with his sexuality. The narrative explores themes of escapism, identity, and the golden age of comic books.

    The 256th Greatest Book of All Time
  3. 3. Money by Martin Amis

    "Money" is a darkly humorous novel that follows the life of John Self, a hedonistic, self-destructive director of commercials, as he navigates the excesses and depravities of 1980s New York and London. His life is filled with overindulgence in food, alcohol, drugs, and women, leading to a downward spiral of self-destruction. The novel is a satire on the excesses of capitalism and the obsession with wealth and materialism, and it also explores themes of identity, self-loathing, and the destructive power of addiction.

    The 323rd Greatest Book of All Time
  4. 4. Gentlemen Prefer Blondes: The Illuminating Diary of a Professional Lady by Anita Loos

    This book is a satirical novel that follows the adventures of a blonde flapper named Lorelei Lee, who uses her looks and charm to climb the social ladder. Lorelei, originally from Little Rock, Arkansas, is a materialistic and somewhat naive woman, who values men for their wealth and status. The story, presented as Lorelei's diary, humorously explores themes of gender, class, and the American pursuit of wealth and status in the early 20th century.

    The 700th Greatest Book of All Time
  5. 5. Pnin by Vladimir Nabokov

    The novel is about a Russian émigré, Timofey Pnin, who is a professor at an American college. Pnin struggles with the complexities of life, language, and American culture, while dealing with the traumas of his past in Russia. The book is a series of loosely connected episodes, filled with humor, pathos, and Pnin's endearing confusion. His struggles and triumphs in academia and his search for a home and identity form the crux of the story.

    The 1566th Greatest Book of All Time
  6. 6. 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 2156th Greatest Book of All Time
  7. 7. The Fan Man by William Kotzwinkle

    The book follows the life of Horse Badorties, a free-spirited, eccentric, and somewhat delusional hippie living in New York City during the 1970s. Horse is obsessed with fans and spends his days collecting them, resulting in a chaotic apartment filled with hundreds of fans. His life is a series of comedic and bizarre adventures as he interacts with a variety of outlandish characters, starts a band, and plans a concert in Central Park. The narrative is infused with a unique blend of humor, absurdity, and a touch of melancholy, capturing the spirit of an era and the eccentricities of its protagonist.

    The 2452nd Greatest Book of All Time
  8. 8. Psmith, Journalist by P. G. Wodehouse

    In this humorous novel, the protagonist, Psmith, takes over a friend's newspaper while he is away. Psmith transforms the paper from a mundane health advice column into a platform for social justice, exposing the corrupt practices of landlords and politicians in New York City. The novel follows his adventures and misadventures in journalism, complete with thrilling chases, gangsters, and witty banter.

    The 2944th Greatest Book of All Time
  9. 9. The Midnight Examiner by William Kotzwinkle

    The novel follows the life of a former serious novelist turned tabloid editor in New York City. The protagonist's life takes a turn when he gets involved with a B-movie actress and a gangster who wants to finance his own movie. The story is a mix of adventure, comedy, and satire, offering a humorous and insightful look into the world of tabloid journalism.

    The 3430th Greatest Book of All Time
  10. 10. A Frolic of His Own by William Gaddis

    The novel explores the complex and often absurd world of American law and litigation. The protagonist is a retired law professor who is embroiled in multiple lawsuits, including one against himself. The narrative is filled with legal documents, depositions, and court transcripts, which serve to critique the convoluted and often nonsensical nature of the legal system. The book also satirizes the American obsession with wealth and property, and the lengths people will go to protect their own interests.

    The 6924th Greatest Book of All Time
  11. 11. A Cool Million by Nathanael West

    The book satirizes the American Dream through the misadventures of its protagonist, a young man who leaves his rural home to seek fortune and success in the big city. Despite his unwavering optimism and adherence to traditional values, he faces a series of increasingly absurd and unfortunate events that strip him of his possessions, dignity, and illusions. The narrative unfolds as a darkly comedic critique of the socio-economic landscape of the time, exposing the harsh realities of capitalism and the myth of equal opportunity.

    The 7180th Greatest Book of All Time
  12. 12. The Extra Man by Jonathan Ames

    The novel follows the story of a young aspiring playwright who moves to New York City with dreams of making it on Broadway. He becomes the protégé of an eccentric older gentleman, a self-styled "extra man" who escorts wealthy widows in the Upper East Side's high society. As the protagonist navigates his new life, he is drawn into a world of old-world manners, transgender escapades, and odd human connections, all while grappling with his own identity and aspirations. The narrative is a comedic and poignant exploration of loneliness, friendship, and the quest for personal authenticity in a city that often feels overwhelming and surreal.

    The 8147th Greatest Book of All Time
  13. 13. All Grown Up by Jami Attenberg

    The novel follows the life of a 39-year-old single, childfree woman living in New York City who is dealing with the societal pressures and expectations of adulthood. Her journey is marked by her struggle to find happiness and fulfillment in her own terms, despite her unconventional lifestyle. The protagonist grapples with her relationships, career, and the looming presence of her family's tragedies, all while trying to understand what it truly means to be "all grown up".

    The 9365th Greatest Book of All Time
  14. 14. The Bear Comes Home by Rafi Zabor

    "The Bear Comes Home" is a unique tale about a talking, saxophone-playing bear who navigates the human world while yearning for true freedom. The bear, who is also the protagonist, struggles with the complexities of human life, including love, art, and the search for self-identity. As he explores the jazz scene, he is caught between his bear nature and his human-like consciousness, leading to a profound exploration of what it means to be free and to be oneself.

    The 10574th Greatest Book of All Time
  15. 15. Less by Andrew Sean Greer

    The novel follows a failing writer about to turn 50, who receives an invitation to his ex-boyfriend's wedding. In order to avoid the event, he decides to accept every literary invitation he's been given and embarks on an around-the-world journey. As he travels from Paris to India, Berlin to Japan, he finds himself facing the big questions about love, aging, and how to live a life that matters.

    The 10787th Greatest Book of All Time
  16. 16. Mister Monkey by Francine Prose

    The novel revolves around the interconnected lives of an eclectic cast of characters, all linked by a lackluster children's musical based on a beloved fictional character, Mister Monkey. Through a series of vignettes, the narrative explores the personal dramas, comedic mishaps, and poignant reflections of the play's actors, the audience members, and even the author of the book on which the play is based. The story delves into themes of art, reality, the impact of small actions, and the human search for meaning, all the while painting a satirical yet sympathetic portrait of the theater world and the varied individuals who find their lives touched by this seemingly trivial production.

    The 11012th Greatest Book of All Time

Reading Statistics

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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.

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