The Greatest Picaresque Books of All Time

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Genres

Picaresque

Picaresque is a genre of literature that typically features a rogue or anti-hero as the protagonist, who travels through various adventures and misadventures, often encountering a diverse cast of characters along the way. These stories are often humorous and satirical, and are known for their episodic structure and lack of a traditional plot. Picaresque novels are often set in the lower classes of society and provide a commentary on social issues of the time.

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  1. 76. 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 1089th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  2. 77. Fanny Hill by John Cleland

    Memoirs of a Woman of Pleasure

    This novel tells the story of a young girl named Fanny Hill who is orphaned at 15 and moves to London where she gets involved in a life of prostitution. The narrative is a series of letters to an unknown woman, detailing her experiences and adventures in explicit detail. Despite the hardships she endures, including exploitation, imprisonment, and heartbreak, Fanny remains optimistic and maintains a sense of innocence throughout the novel.

    The 1132nd Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  3. 78. The Water Margin by Shi Naian

    Outlaws of the Marsh

    "The Water Margin: Outlaws of the Marsh" is a classic Chinese novel set during the Song dynasty, revolving around 108 outlaws who gather at Mount Liang to form a sizable army. The narrative explores themes of rebellion, loyalty, and justice, as these bandits challenge the corrupt and oppressive government. Despite their status as outlaws, they follow a strict code of honor and righteousness, often assisting the poor and the weak. The book is a blend of history, folklore, and mythology, offering a vivid portrayal of the political and social dynamics of the era.

    The 1151st Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  4. 79. True History of the Kelly Gang by Peter Carey

    This historical novel is a fictionalized account of the life of Australian outlaw Ned Kelly, told in the form of a journal written to his daughter. The narrative explores Kelly's life from childhood, his family's struggles with poverty and the law, his involvement in horse thievery, and his eventual formation of the Kelly Gang. The story culminates with the gang's infamous standoff with the police at Glenrowan, providing a humanizing perspective on a figure often portrayed as a ruthless criminal.

    The 1154th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  5. 80. The Twelve Chairs by Ilya Ilf, Evgeniy Petrov

    In this satirical novel, a former nobleman and a con artist form an unlikely partnership in pursuit of hidden treasure. After the Russian Revolution, fortunes are overturned, and the nobleman learns that his family jewels were sewn into one of the twelve chairs from a dining room set. As the chairs have been scattered by the new Soviet regime, the duo embarks on a wild chase across the USSR, encountering a colorful cast of characters and navigating the absurdities of the communist system. Their quest for wealth is a humorous reflection on human greed and the ironies of fate in a society undergoing radical change.

    The 1161st Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  6. 81. The Horse's Mouth by Joyce Cary

    The novel follows the life of Gulley Jimson, a boisterous, eccentric, and impoverished painter in London who is constantly in search of the perfect canvas to express his artistic vision. Despite his numerous struggles with society's norms, financial difficulties, and his own physical health, Jimson remains unflinchingly dedicated to his craft. His relentless pursuit of artistic truth and beauty, often at the expense of personal relationships and societal expectations, paints a vivid picture of the passionate, self-destructive artist archetype.

    The 1165th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  7. 82. The Demons by Heimito von Doderer

    The Suburb of Women

    The novel explores the intricate lives and psychological depths of a vast array of characters in interwar Vienna, focusing on the transformative experiences and moral dilemmas they face. Through a richly woven narrative, the book delves into themes of power, guilt, and redemption, set against the backdrop of a society on the brink of monumental change. The story masterfully intertwines the personal and political, revealing the complex interplay between individual desires and societal pressures. Through its detailed portrayal of Vienna and its inhabitants, the novel offers a profound commentary on the human condition, examining how the demons within and without shape our destinies.

    The 1175th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  8. 83. Carmen by Prosper Mérimée

    A Study in Temperament

    "Carmen" is a novella that tells the tragic story of the downfall of Don José, a naïve soldier who is seduced by the wiles of the fiery gypsy, Carmen. José abandons his childhood sweetheart and deserts from his military duties, yet he is unable to tame Carmen's free spirit. Carmen's lawless nature leads her to fall in love with a successful bullfighter and ultimately seals her fate.

    The 1176th Greatest Book of All Time
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  9. 84. The Inimitable Jeeves by P. G. Wodehouse

    This book is a collection of humorous short stories set in 1920s London, featuring the iconic characters of a wealthy, hapless young man and his intelligent, resourceful butler. The narrative revolves around the young man's various misadventures, often involving his eccentric friends and relatives, and the butler's ingenious solutions to save the day. The stories are characterized by their witty dialogue, slapstick humor, and satirical commentary on the British upper class.

    The 1185th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  10. 85. The Enchanted Wanderer by Nikolai Leskov

    and Other Stories

    "The Enchanted Wanderer" is a collection of short stories that follow the life of a Russian serf, Ivan Flyagin, who is destined to wander forever and never die. Throughout his travels, he experiences a myriad of adventures including becoming a monk, being captured by Tartars, and falling in love. The stories are filled with folkloric elements and offer a vivid depiction of 19th-century Russian society.

    The 1205th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  11. 86. The Floating Opera by John Barth

    The novel is a first-person narrative told by an aging man who contemplates suicide on his birthday. He recounts the events of his life, including his love affairs, his law career, and his relationships with his friends and neighbors in a small Maryland town. As he reflects on the absurdity of life, he questions the value of existence and the nature of reality, resulting in a darkly humorous and philosophical exploration of the human condition.

    The 1213th Greatest Book of All Time
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  12. 87. Thank You, Jeeves by P. G. Wodehouse

    In this humorous story, a British aristocrat and his valet find themselves in a series of comedic situations. The aristocrat's banjo playing has led to his eviction from his apartment, forcing him to take refuge in the country, where he becomes embroiled in a scheme to steal a policeman's helmet for a wager. Meanwhile, his valet must navigate a complex love triangle involving a fiery-tempered opera singer, a mild-mannered poet, and a jealous fiance. The pair's quick wit and unflappable demeanor carry them through these and other predicaments, providing plenty of laughs along the way.

    The 1221st Greatest Book of All Time
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  13. 88. The Adventures of Peregrine Pickle by Tobias Smollett

    In Which Are Included Memoirs of a Lady of Quality

    "The Adventures of Peregrine Pickle" is a picaresque novel that follows the life of the titular character, a young man of wealth and status, who is known for his mischievous behavior and adventures. The novel is a satirical commentary on 18th-century British society, showcasing the protagonist's encounters with various characters, from nobility to the impoverished. Despite his numerous escapades and romantic entanglements, Peregrine's life takes a turn when he loses his fortune, leading to his imprisonment and eventual redemption.

    The 1226th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  14. 89. The History Of Gil Blas Of Santillana by Alain-René Lesage

    or, The Adventures of a Young Man

    This classic picaresque novel follows the adventures and misadventures of the young Spaniard, Gil Blas, as he navigates through the ups and downs of life, from poverty to wealth, from servant to nobleman, across the varied landscape of 17th-century Spain. Through a series of engaging episodes, the protagonist encounters a wide array of characters, from rogues and thieves to honest men and true friends, experiencing firsthand the vices and virtues of humanity. The narrative, rich in satire and social commentary, humorously critiques the corruption and folly of society, while also exploring themes of fate, ambition, and morality. Through Gil Blas' journey, the reader is offered a vivid and entertaining portrait of Spanish life and culture during the period.

    The 1233rd Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  15. 90. Something About Eve by James Branch Cabell

    A Comedy of Fig-Leaves

    "Something About Eve" is a captivating novel that delves into the complex and mysterious life of Eve, a woman who possesses an irresistible charm and allure. Set in a small town, the story follows Eve's interactions with various characters, each of whom becomes infatuated with her in their own unique way. As the narrative unfolds, secrets are revealed, relationships are tested, and the true nature of Eve's enigmatic persona is gradually unveiled. With its richly developed characters and thought-provoking themes, this book offers a compelling exploration of desire, identity, and the power of seduction.

    The 1414th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  16. 91. The Path to the Nest of Spiders by Italo Calvino

    The novel is set in Italy during World War II and follows the journey of a young boy who joins the Italian resistance against the Nazis. The story is a coming-of-age tale that explores the boy's struggle to find his identity amidst the chaos of war. Along the way, he encounters various characters, each with their own stories and perspectives on the war, which further shape his understanding of the world. The title refers to a hidden nest of spiders the protagonist discovers, symbolizing the hidden complexities of life and war.

    The 1418th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  17. 92. The Sot-Weed Factor by John Barth

    "The Sot-Weed Factor" is a satirical, picaresque novel set in the late 17th century, revolving around an innocent poet from London who is tricked into becoming a tobacco sot-weed factor in Maryland. The protagonist's misadventures, filled with mistaken identities, pirates, Native Americans, and a wide array of eccentric characters, mirror the challenges and absurdities of America's early colonial period. The narrative, rich in historical detail and parody, explores themes of identity, truth, and the nature of reality.

    The 1422nd Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  18. 93. Cakes And Ale Or, The Skeleton In The Cupboard by W. Somerset Maugham

    The Skeleton in the Cupboard

    This novel is a satirical exploration of literary society, focusing on the life and posthumous reputation of a celebrated author. Through the eyes of the narrator, a writer named Ashenden, the story delves into themes of hypocrisy, fame, and the contrast between public image and private reality. The narrative weaves together the past and present, revealing the complexities of human relationships and the often-discrepant nature of personal versus public personas. At its core, the book critiques the literary establishment's pretensions and the way it shapes legacies, all while pondering the true nature of art and integrity.

    The 1431st Greatest Book of All Time
    Purchase from Amazon
  19. 94. Camera Obscura by Nicolaas Beets

    Bladen uit het dagboek van Hildebrand

    "Camera Obscura" is a collection of humorous and satirical sketches that provide a vivid picture of 19th-century Dutch society. It explores the social and domestic life of the middle classes, their habits, their social pretensions, their pleasures and their follies. The book also includes a series of character studies, often based on the author's acquaintances, which are presented in a light-hearted and often ironic tone.

    The 1463rd Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  20. 95. Don Juan by Lord Byron

    A Satirical Epic Poem

    This epic satirical poem tells the story of Don Juan, a handsome, charming young man from Spain who gets into various adventures and romantic escapades throughout Europe and the Ottoman Empire. Throughout his journey, he encounters a variety of characters, including pirates, sultans, and aristocrats, while also engaging in numerous love affairs. The narrative, filled with humor, irony, and social commentary, serves as a critique of societal norms and conventions, particularly those related to love and morality.

    The 1466th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  21. 96. The Little Golden Calf by Ilya Ilf, Evgeniy Petrov

    The Adventures of Ostap Bender

    The book is a satirical novel that follows the adventures of a charming con artist in the Soviet Union during the 1920s. The protagonist, with a combination of wit, luck, and audacity, navigates through the absurdities of the Soviet bureaucracy and the remnants of the pre-revolutionary elite in pursuit of a mythical treasure. His journey is marked by a series of humorous episodes that expose the contradictions and ironies of the early Soviet society, ultimately offering a sharp critique of human greed and the folly of the era's political and social systems.

    The 1481st Greatest Book of All Time
    Purchase from Bookshop.org
  22. 97. The Magician of Lublin by Isaac Bashevis Singer

    This novel tells the story of Yasha Mazur, a talented and renowned 19th-century Jewish magician living in Poland. Yasha is a complex character, torn between his own desires and the expectations of his religious community. He leads a double life, juggling his career, his marriage, and his multiple affairs. As he grapples with his conflicting identities, Yasha is forced to confront his own moral failings and the consequences of his actions. His journey is one of self-discovery and redemption, offering a nuanced exploration of faith, love, and the human condition.

    The 1501st Greatest Book of All Time
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  23. 98. Guzmán de Alfarache by Mateo Alemán

    Primera parte de la vida del pícaro Guzmán de Alfarache

    "Guzmán de Alfarache" is a picaresque novel that follows the life of the protagonist, Guzmán, a rogue who recounts his life story from his humble beginnings to his eventual downfall. Through his narrative, he provides a moralizing commentary on various aspects of Spanish society in the 16th century. The book explores themes of morality, religion, and social criticism, and is considered a precursor to the modern novel.

    The 1523rd Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  24. 99. The Late Mattia Pascal by Luigi Pirandello

    The Late Mattia Pascal (Italian: Il fu Mattia Pascal [il ˈfu mmatˈtiːa paˈskal]) is a 1904 novel by Luigi Pirandello. It is one of his best-known works and was his first major treatment of the theme of the mask.

    The 1525th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon
  25. 100. Myra Breckinridge by Gore Vidal

    This novel follows the story of Myra Breckinridge, a transgender woman who moves to Hollywood with the plan of both achieving stardom and challenging traditional gender roles and sexuality. The protagonist uses her wit, charm, and sexual appeal to manipulate those around her to further her own ambitions. The book is a satirical exploration of gender, sexuality, and the American Dream, set against the backdrop of 1960s Hollywood.

    The 1530th Greatest Book of All Time
    Purchase from Bookshop.org or Amazon

Reading Statistics

Click the button below to see how many of these books you've read!

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.

Download

To download this list as a CSV file, please log in to your account. Once logged in, you'll be able to download the data for use in spreadsheet applications.

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