Mark Twain was one of a kind. An icon in his own time, everything about his life smacked of the tall tales he frequently told. Born with the appearance of Halley’s Comet and passed away with the comet’s next appearance, Twain lived life on the edge—politically, ideologically, and personally.
Christened Samuel Langhorn Clements, he adopted his pseudonym from the insider terminology of his early career as a steamboat captain on the Mississippi River. He then used that pseudonym to craft a literary reputation that endures to this day—one of the funniest, best-travelled, and most astute critics of the American era that followed the Civil War.
Twain’s reputation has repeatedly come under fire for what today seem like regressive depictions of black Americans and Native Americans. But in his day Twain staked out a position as one of the great voices of progressive values and a champion for what would one day become the Civil Rights movement.
Twain would have been the first to admit he was not perfect, but to take him out of the ethical wasteland of post-Civil War America and drop him into 21st-Century Cancel Culture does the man a disservice. The best Mark Twain books held up a mirror to the ugliness of his surroundings—there was nothing to be gained by pretending they didn’t exist. Twain pointed a bright spotlight on some of the greatest evils of his age.
There’s no upending Twain’s legacy. He’s just too good. Here are the 18 Mark Twain books everyone should read at least once.
17- The Gilded Age
The Gilded Age (Illustrated First Edition): 100th Anniversary Collection
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Twain’s first published novel is a collaboration with Charles Dudley Warner, published in 1873. While not held up among the best Mark Twain books, its title, borrowed from Shakespeare, was widely adopted to describe the American era in which it was written—an era of big bosses, political machines, robber barons, laissez-faire politics, and deep class inequality.
The story concerns the follies of land speculation, along with the squabbles to claw from poverty to the upper class and the desperation of the upper crust to remain so. It’s also a treatise on proto-feminism, with various heiresses and wives entering the political and fiscal chess matches dominated by men ravenous for riches.
16- Tom Sawyer Abroad
Tom Sawyer Abroad: AND Tom Sawyer, Detective (Wordsworth Classics)
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While their first adventures remain the quintessential Mark Twain books, Twain returned to the characters several times. How could he not? Sequels practically sell themselves.
In Tom Sawyer Abroad, Twain executed a dream-team mashup of his two most popular, bestselling multi-volume properties—the adventures of Tom and Huck, and the series of travel memoirs he published under titles like The Innocents Abroad and A Tramp Abroad.
Tom Sawyer abroad drops our favorite antebellum bad boys, along with Huck’s freed-slave companion Jim, onto the African continent by a steampunk-ready hot air balloon inspired by the writings of Jules Verne. Tom, Huck, and Jim see the Pyramids and the Sphinx, while contending with lions, bandits, and deadly fleas.
Africa is notably missing from Twain’s other travel writings. In this book, Twain seems to live vicariously through Tom, Huck, and Jim (although he writes Africa like someone who has never been there).
Despite being named after its better-selling hero, Twain, mindful of his bolstered literary reputation, revives his most celebrated conceit by continuing the tradition of first-person narration through Huck Finn’s eyes.
15- The Man That Corrupted Hadleyburg and Other Stories and Essays
The Man That Corrupted Hadleyburg and Other Stories and Essays
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The central story of this anthology is one of Twain’s most biting and one that rings true in an era where self-righteousness and demagoguery sometimes upset actual virtue.
The titular town of Hadleyburg is proud of its reputation as an honest and upright place, but when the residents offend a passing stranger, he devises a fiendish trap to expose the residents of Hadleyburg for the venal sinners they are.
He deposits a bag of gold in the town square with a note that it is a reward to the resident who gave him a great piece of advice. He invites the citizens to guess what that advice was. Initially proud of their altruism, the residents of Hadleyburg predictably succumb to greed, squabbling over the fortune with mounting self-importance until the truth is inevitably exposed in an escalating series of misadventures that drags Hadleyburg through the dirt.
14- Fenimore Cooper’s Literary Offenses
Fenimore Cooper's Literary Offenses
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Want to read Twain as he rips one of his contemporaries a new one? This short read finds Twain taking author James Fenimore Cooper to the woodshed, lambasting him for violating eighteen separate literary “commandments” and committing 114 (of 115) literary offenses. Examples: “The tale shall arrive somewhere and accomplish something.” Or … “The author shall use the right word and not its second cousin.”
Fenimore Cooper was well respected in his day. His defenders found Twain’s essay out of line and way off-base, but they acknowledged that it was hilarious.
13- The Jumping Frog
The Jumping Frog: A Fantastic Story of Action & Adventure (Annotated) By Mark Twain.
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As pure of a lark as any of Twain’s books, The Jumping Frog (aka The Celebrated Jumping Frog of Calaveras County) is required Twain reading because it represented his earliest publishing success.
The popular story concerns Jim Smiley and his champion jumping frog Dan’l Webster, tricked into losing a bet by a cheating drifter. The story unfurls from the point of view of a storyteller named Simon, whose rambling interaction with the narrator satirizes the very pointlessness of the tall tales we regale each other with—quite an admission for one of America’s great tall-tale tellers.
12- Letters from the Earth
Letters from the Earth
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Twain wrote nonfiction throughout his career, much of it travel memoirs. However, this posthumously-published collection of essays is the most illuminating glimpse into his mind out of any of Mark Twain’s books.
It’s also a glimpse of Twain at a low point in his life—aging, having just become a widower, outlived two of his four children (he would ultimately outlive a third), and fallen deeply into debt, Twain’s musings on religion, politics, and morality are sarcastic bordering on bitter. The humorous and humane voice we know and love has lost none of its spark, though. Twain’s latter-day essays are a treasured time capsule of early-20th century progressive values.
11- Roughing It
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The wry humor and narrative flair that characterize books by Mark Twain are on full display here—albeit in nascent form–in this early travel-lit memoir, a prequel to his wildly successful Mark Twain book Innocents Abroad. Rather than let loose on Europe and the Holy Land, in Roughing It Twain takes on the byways of his own vast country.
Like an antebellum Anthony Bourdain, Twain bustles through a series of adventures, including a stint in the Wild West, a disastrous and short career as a reluctant Confederate soldier, a stagecoach journey with his brother to Nevada, followed by a freewheeling adventure to Salt Lake City, and a cruise all the way to the Kingdom of Hawaii.
On the way, he prospects for gold, speculates in real estate, and takes up the pen for the first time. No wonder Twain’s prose is so engrossing throughout his career—the man got out there and lived.
10- The Mysterious Stranger and Other Stories
The Mysterious Stranger and Other Stories
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Sometimes even Twain was defeated by one of his creations. He tried, unsuccessfully, on several occasions to write a book with Satan as the protagonist. Several of the fragmentary versions of this unfinished Mark Twain book are set in Twain’s fictional town of St. Petersburg, Missouri; one of them even partners Satan (referred to euphemistically as “No. 44”) with Tom Sawyer and Huck Finn!
The Mysterious Stranger, the most complete but still arguably unfinished version of the concept, is a crown jewel of Twain apocrypha. It’s a fascinating misfire that rambles through 15th-century Austria in the early days of the printing press, while musing on the duality of the “Waking Self” and the “Dream Self.”
9- Diaries of Adam and Eve
Diaries of Adam and Eve
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Whereas the Devil flummoxed him, Twain found in Adam and Eve Biblical characters much more in his wheelhouse. This collection of short stories, written late in Twain’s life, are often seen as a love letter to Twain’s wife Livy, with Adam modeled after himself and Eve after Livy.
Adam’s diary expresses perplexity at his newfound female companion, her confidence and idiosyncrasy, which he struggles to parse with his analytic mind. He is even more baffled with the offspring that Eve inexplicably produces, at first mistaking baby Cain for a kind of fish or bear.
Eve’s voice, by contrast, takes a lighter approach to her own creation and later her death, with the fall from grace and expulsion from the Garden thrown into the mix. It’s an endearing look at the “battle of the sexes” with a decidedly Twainian spin.
8- Pudd’nhead Wilson
Pudd'nhead Wilson, and Those extraordinary twins. By: Mark Twain: A NOVEL (World's classic's)
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Twain returns to the “switched-at-birth” conceit he toyed with in The Prince and the Pauper while leaning into the racial politics he broached in Adventures of Huckleberry Finn to create one of the bleakest Mark Twain books in print
Pudd’nhead Wilson tells the story of two baby boys who resemble each other. In this case, Tom Driscoll is born the heir of a plantation master; Chambers is born the son of a slave, but with only one black great-great-great-great grandparent, he is nearly indistinguishable from a white child, despite the mixed-race family line persisting in slavery.
Fearing being “sold down the river,” Chambers’ slave mother switches the babies at birth, so that Tom is raised a slave and Chambers is raised as Tom. Pudd’nhead Wilson is decidedly darker than some of Twain’s other work on heavy subjects. The title character is a trial attorney who proves that Tom is not only the real Tom, but also guilty of murder. Whether delivered from slavery or returned to it, there’s no real happy ending possible in the morally bankrupt world of Pudd’nhead Wilson.
7- Life On The Mississippi
It’s well-known that Sam Clements stole his pen name from “mark twain,” a vernacular used by Mississippi River steamboat pilots to indicate water that was safe to navigate. “Twain” as in “two,” or two fathoms—roughly twelve feet deep in total, deep enough to accommodate a steam boat.
Decades after his formative years as a steamboat pilot, Twain recounted his training at the hands of colorful pilot Horace E. Bixby, in the first half of the memoir Life on the Mississippi. The second half is his return to his old stomping grounds, on a recent river trip from St. Louis to New Orleans, peppered by complaints about the encroaching popularity of railroad, the decline in the beauty of the passing architecture, and various tall tales and cutting anecdotes. As with the best books by Mark Twain, this book sails on the pleasure of watching the master at his most wistful, musing, and wry.
6- The Innocents Abroad
The best-selling Mark Twain book in his lifetime was not Tom Sawyer or Huck Finn; rather, it was this early nonfiction book, the narrative equivalent of a FOMO-inducing image-crafting Instagram story. In it, he recounts his “Great Pleasure Excursion,” a river cruise through Europe and the Holy Land.
In addition to providing an early example of Twain’s knack for raucous humor and keen observation, it’s one of the all-time great travel books, a contemporaneous 19th-century snapshot of cities like Paris, Marseille, Gibraltar, Rome, Odessa, and Jerusalem. Throughout, Twain muses on the banality of the modern, juxtaposed with the grandeur of history.
5- The Prince and The Pauper
Set in Tudor-era England, Twain’s first attempt at historical fiction is a classic take on the “twins separated at birth” conceit, with an added interrogation of privilege and class consciousness. The titular prince and pauper are not actually twin brothers, but they were born on the same day and resemble each other closely.
The prince is Edward Tudor, historical son of King Henry VIII and his successor as King Edward VI (although he died a teenager after a few years’ reign. Twain’s book acknowledges his short life and reign, but downplays the historical Edward’s penchant for cruelty and misogyny.)
This more benign Edward meets and befriends Tom Canty, his street-urchin doppelganger, and for a lark they switch places like a medieval Parent Trap. Masquerading as Edward, Tom is a fish-out-of-water as the pressures of royalty hit home for him.
Masquerading as pauper Tom, Prince Edward, on the other hand, gets a harsh look at the lot of his impoverished subjects-to-be, which teaches this fictitious Edward a valuable lesson in empathy of the ruler for the ruled. If only …
4- A Connecticut Yankee in King Arthur’s Court
In a way, A Connecticut Yankee in King Arthur’s Court is Twain’s middle finger to Sir Walter Scott. Scott romanticized medieval chivalry. He ennobled its attendant wars and battles so effectively that the Confederate government borrowed his rhetoric and duped its own men into believing they were heroic and noble to die horribly in the Civil War. Twain bats back at Sir Walter’s chivalrous pretence by dropping Hank Morgan, a 19th-century arms manufacturer, into the cradle of chivalric legend—6th Century England and the court of King Arthur.
Hank wins followers with his demonstrations of modern weapons technology, presumed to be sorcerery. Next thing you know, the England of the dark ages is armed with gatling guns and electric fences against a pitifully underprepared Papal army, sent to unseat the blasphemous Hank.
Out of all the books by Mark Twain, this book is the most rife with anti-war satire, including the wizard Merlin’s cruel trick on credulous soldiers by casting a false “invisibility” spell on them to give them courage in the battle—like “The Emperor’s New Clothes” in reverse. His gunpowder-age sorcery, however, can’t protect King Arthur from the disastrous disloyalty of Sir Launcelot and Queen Guinivere, nor can it protect Hank from the heartbreak he himself will face as he adapts to medieval life.
3- The Adventures of Tom Sawyer
While he had written several popular short stories and memoirs, The Adventures of Tom Sawyer was Twain’s first crack at novel-length fiction. It flopped in its initial release, but gained traction as Twain’s career bloomed and went on to become his best-selling novel in his lifetime, a full-throated American classic and one of the best Mark Twain books.
The third-person narrative follows Tom Sawyer, a crafty “bad boy” with a good heart, who careens through a series of madcap adventures.The story also hints at things to come by introducing a peripheral character—an orphaned gutter-urchin named Huckleberry Finn whom Tom befriends.
Tom also falls for the new judge’s daughter, Becky, and runs afoul of the villainous Injun Joe as he hunts for buried treasure in McDougal’s cave. Injun Joe, irredeemably malevolent and identified by an epithet for Native Americans, remains a controversial figure, a stereotype that has not aged well.
At best, Joe’s treatment remains a teachable moment in one of the quickest reads in the American canon, a book that makes it easy for children and young adults to fall in love with reading as they live vicariously through the titular over-confident scamp. Out of all the books by Mark Twain, Tom Sawyer is still the most fun.
2- Adventures of Huckleberry Finn
Many Twain titles are classics, but Adventures of Huckleberry Finn stands alone, one of the few novels that vies with Moby-Dick and The Great Gatsby for the title of “Great American Novel.”
The Adventure of Tom Sawyer is a rip-roaring adventure story with life-and-death stakes, but Huck Finn is something else entirely. This buddy adventure story shows us the world from the first-person point-of-view of street rat Huck Finn, a minor character in Tom Sawyer. By adopting his perspective, Huck Finn also becomes a first-of-its-kind tour de force of American vernacular, a time capsule of the verbal tics of the contemporary rural poor that linguists baffle over to this day.
Crude and uneducated, Huck Finn is a product of his time—the slave-holding South, when terms we consider horrible racial epithets were in common usage. This jarring use of the N-word has caused recent generations to peg Twain as a racist, his book beyond redemption.
They are all wrong. Relative to his time period, Twain was a cutting-edge progressive, active in anti-slavery and anti-colonialist movements on a global basis with his knack for humane common sense. Huck Finn itself is an interracial buddy road story well ahead of its time.
The buddies in this case are Huck Finn and Jim, a runaway slave, as they attempt surreptitiously to navigate a river raft up the Mississippi River to the free states, encountering an indelible cast of scoundrels along the way and featuring a triumphant return of Tom Sawyer in the final act.
Unschooled but big-hearted, modern eyes peg Jim as a cipher for black stereotypes. But Twain didn’t write Huck Finn in the era of “Black Lives Matter.” He wrote it in the era of “Jim Crow,” the era of unpunished lynching, within living memory of the Civil War. Jim’s flight to freedom puts the hypocrisies of institutionalized racism up on a pillory where you can throw eggs at it—exactly where it belongs. Truly the best of the best Mark Twain books.
1- Personal Recollections of Joan of Arc
This may be the strangest Mark Twain book. Twain asked that his authorship of Recollections of Joan of Arc be kept secret and the book published anonymously. This passion project, born of his fascination with the titular subject, isn’t funny. At least, it doesn’t revel in Twain’s usual wry sense of humor. But Twain, in writing the last book that would be published in his lifetime, wanted his subject to be taken as seriously as he took it. (Of course, the authorship didn’t stay secret for long.)
While contemporary criticism has not been kind to it, Personal Recollections of Joan of Arc is the book that Twain himself considered his finest and most important, even scolding young readers that they should read it instead of his books about “bad boys.” Oops!
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