When the Ajax made its second voyage in March 1866, Mark Twain was on board. He had persuaded the editors of the prestigious Sacramento Union to pay him to write correspondence from the islands. The trip came at an opportune time: Twain had been getting sick of California and the indigent, itinerant life he led there. Despite the success of his jumping frog story, he remained a poor freelancer. “I am tired being a beggar,” he wrote his brother, “tired being chained to this accursed homeless desert.” In Hawaii he hoped to find a new world to explore, and the chance to capitalize on his recent triumph.

In his four months in Hawaii he wrote twenty-five letters for the Union, watched a volcano erupt, saw native girls skinny-dip in the sea, ate horrifying amounts of tropical fruit, and tried and failed to surf. The contrast with San Francisco exhilarated him: here he walked on coral, not cobblestone, and smelled jasmine and oleander instead of offal and sewage. Like Stoddard, he found the balmy, beautiful setting deeply relaxing: during five weeks in Maui, he took a much-needed holiday. “I have not written a single line, & have not once thought of business, or care, or human toil or trouble or sorrow or weariness,” he wrote his sister‑in‑law. But Hawaii wasn’t purely a vacation: it also gave Twain invaluable training in travel writing, the genre that would produce his first major book, "The Innocents Abroad." He took Union readers on a galloping tour of a kingdom rife with lurid customs and costumes, rich with sugar and whales, infested with British, French, and American interlopers, and governed by the last of the great Hawaiian kings, Kamehameha V.

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In the midst of this came Twain’s first big scoop: a journalistic coup that amply repaid the Union’s investment in him. On May 3, 1866, the USS Hornet sank off the coast of South America on its way to San Francisco. On June 15, fifteen survivors washed ashore on Hawaii’s Big Island. They had spent the last forty-three days in a longboat, subsisting on dwindling rations of salt pork and sea biscuits and the occasional dolphin. At the time, Twain was in bed, recovering from a bad case of saddle sores. But when eleven of the Hornet’s sailors arrived at the Honolulu hospital, he arranged for a friend to carry him there on a stretcher. One invalid to another, he interviewed the men about their ordeal and wove their answers into a suspenseful tale. The Union published it on July 19, 1866. The first account of the shipwreck to appear in the American press, it caused a sensation. Less than a year after the jumping frog made the nation howl with laughter, Twain tried a different key—drama—and scored another hit.

He was on fire, and he knew it. As soon as he returned to San Francisco in August 1866, he set about milking the Hornet saga for everything it was worth. He traveled to the Union’s offices in Sacramento to demand $300 for the scoop, and then turned around to expand the story into a magazine-length piece that he sold to Harper’s Monthly. But by far the most important outcome of his Hawaii adventure was his debut as a public speaker: a decision that, more than any others, would eventually seal his ascent into the upper stratosphere of national stardom.

His motive, as always, was money. He recalled Artemus Ward, whose San Francisco debut on November 13, 1863, had taken in more than $1,000 at the door. Ward had leveraged his popularity as a writer into a lucrative career on the lecture circuit, and now Twain hoped to do the same. His writing gigs paid irregularly, and neither of his collaborations with Harte had panned out. He wanted to turn his Union letters into a book, but devoting himself to the manuscript would require covering his living expenses. So he started writing a lecture on his latest area of expertise: Hawaii.

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One rainy evening, Twain stopped by his old office at the Morning Call to ask for advice. He “entered in a sort of uncertain way, clad in a thin black frockcoat—his only protection from the storm,” recalled George Barnes, his former boss. He laid a damp manuscript on an editor’s desk and demanded his opinion. “I’ve been to Harte and Stoddard, and the rest of the fellows, and they say, ‘Don’t do it, Mark; it will hurt your literary reputation.’” The editor read the lecture while Twain dried his soaked clothes by the fireplace. “Mark,” the editor asked after an interval, “which do you need most at present, money or literary reputation?” “Money!” Twain replied. “Then go to Maguire, hire the Academy of Music on Pine street, and there deliver the lecture. With the prestige of your recent letters from the Hawaiian islands, you will crowd the theater.”

Happily, Twain obeyed. He booked the city’s largest venue for the night of October 2, 1866, and launched a marketing campaign complete with handbills and newspaper ads. These were vintage Twain: hoaxing, wry, sliding between sharply different registers:

A SPLENDID ORCHESTRA

Is in town, but has not been engaged.

ALSO,

A DEN OF FEROCIOUS WILD BEASTS

Will be on exhibition in the next Block.

MAGNIFICENT FIREWORKS

Were in contemplation for this occasion,

but the idea has been abandoned.

A GRAND TORCHLIGHT PROCESSION

May be expected; in fact, the public are privileged

to expect whatever they please.

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The doors opened at seven. “The Trouble to begin at 8 o’clock.”

Twain’s promotional push set off a wave of advance sales. “We have no doubt the house will be crowded,” declared the Call. “Those who wish to get seats will do well to go early,” counseled the Evening Bulletin, “for the indications of a grand rush are unmistakable.” The rumor mill went into high gear: Twain would talk about mermaids, or perform native dances. Nobody wanted to miss what promised to be one of the biggest premieres on the San Francisco stage.

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Several years later, Twain remembered feeling deathly afraid as the night drew near. He couldn’t sleep. He couldn’t eat. He was “the most distressed and frightened creature on the Pacific coast,” reviewing his lecture notes until all of the humor drained from them. “I grieved that I could not bring a coffin on the stage and turn the thing into a funeral.” Yet he had already committed himself to making the show a success by hyping it relentlessly. Now all that remained was to deliver a performance worthy of his promises.

On the evening of October 2, 1866, the Academy of Music swelled to capacity. From the footlights to the family circle, the house was packed. “It is perhaps fortunate that the King of Hawaii did not arrive in time to attend,” cracked a journalist, “for unless he had gone early he must have been turned away.” The fashionable men and women of “the regular opera ‘set’ ” turned out in full. The wife of the current California governor, Mrs. Frederick Low, sat in a box. Even Harte came to show his support. He arrived with “a big claque,” an observer later recalled, almost certainly with Stoddard in tow.

At eight o’clock, the crowd started stomping its feet. When Twain appeared in the wings, they broke into thunderous applause. He ambled forward with a lurching, graceless gait, his hands thrust in his pockets. “I was in the middle of the stage,” he recalled, “staring at a sea of faces, bewildered by the fierce glare of the lights, and quaking in every limb with a terror that seemed like to take my life away.” For several moments he stood silently staring, as the energy in the house ripened to an unbearable pitch. Then the words came: slow and deliberate, quirky and crude—the voice of the frontier, drawing its listeners under.

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For seventy-five minutes, they laughed, clapped, and cheered. A “brilliant success,” raved the next day’s Evening Bulletin. Twain met the demands of a “serious” lecture by covering the islands’ economy, politics, history—yet he deftly interwove these with a current of comic tension that kept his audience on a hair trigger, primed to ignite at any moment. An absurdity might slip discreetly into the stream of his story, and then another, sparking laughter that rose and crested just as he suddenly shifted gears, delivering a passage of such heartfelt eloquence that the house fell solemn and silent. This was more than humor: it was “word painting,” said a reporter, a tapestry of anecdotes and images recorded by Twain’s all-seeing eye. He didn’t just make people laugh. As with “Jim Smiley and His Jumping Frog,” he brought a faraway place to life.

Ever since Twain first began writing, he had tried to give his words the flavor of living speech. Dashes, italics, phonetically transcribed dialect—these were meant to make readers hear a speaker’s special vibrations, the glottal tics of different tongues. Onstage, he could do this directly, breaking free of the filter that confined his written voice. He could feel out his audience, refine his rhythms. Unlike the spiritualists, suffragists, and fake scientists then sweeping lyceum halls across the country, he didn’t declaim in the usual authoritative style. He took a more intimate tone. He wanted to connect. He gazed at people’s faces. He played with his hair, kneaded his hands. He looked nervous, and dressed carelessly. He wasn’t a smooth performer, and this was the key to his peculiar charm. He didn’t hold himself apart; he talked plainly, unpretentiously. He brought people inside the joke. He made them feel like he belonged to them.

Even Harte came away impressed. He had warned his friend not to degrade himself by perpetrating an act of popular entertainment, and been proved wrong. At least he had the honesty to admit his mistake. In a glowing review for a prominent eastern paper, the Springfield Republican, Harte said Twain “took his audience by storm.” He couldn’t resist offering a few criticisms, faulting the lecture’s “crudeness,” “coarseness,” and “plainness of statement.” But he also discerned a deeper virtue in Twain’s performance: its Americanness. Twain’s humor belonged to “the western character of ludicrous exaggeration and audacious statement,” Harte wrote, “which perhaps is more thoroughly national and American than even the Yankee delineations of Lowell.” James Russell Lowell, the former editor of the Atlantic Monthly, had depicted the dialect of rural New England in a famous book called "The Biglow Papers"—yet it paled in comparison to Twain, who achieved a much richer rendering of the American vernacular.

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He captured not only the patterns of everyday speech but their spirit: not only how Americans talked but how they thought. That night at the Academy of Music, he premiered a personality that, by the end of the century, would be enshrined in the national psyche. It was especially well suited for the modernizing nation that emerged after the Civil War: quotable, photogenic, endlessly self-aggrandizing. It would flourish in the first age of mass media, live perpetually in the public eye. It wasn’t entirely the man himself but an amplified, embroidered version—and on October 2, 1866, this character took its first step into the spotlight. “I think I recognize a new star rising in this western horizon,” observed Harte, with a tinge of envy.

Twain’s total take, after expenses, came to $400. Not bad for a night’s work, but he hoped to do better. So he took his show on the road, embarking on a hastily organized tour of California and Nevada. He stormed Sacramento, and then cut deep into mining country, conquering a string of one-horse hamlets in quick succession: Marysville, Grass Valley, Red Dog, You Bet—former boomtowns in slow-motion busts, desperate for theatrical distraction. Twain kept expectations high, plastering each town with advance publicity and indulging in offstage antics that enhanced his personal myth. Papers ran reports of the performer guzzling gallons of beer in a single sitting, preparing for lectures with gin and relaxing afterward with whiskey, smoking cigars and telling stories in his trademark drawl until dawn.

The climax came in Virginia City, where Twain staged a glorious homecoming. On October 31, 1866, he played to eight hundred people at Maguire’s Opera House— the same place where he had seen Artemus Ward perform a few years earlier—and won them over before saying a word. A “hurricane of applause” greeted him as soon as the curtain lifted, recalled Steve Gillis, who came to cheer for his old roommate. The Territorial Enterprise embraced its native son, hastening to take credit for his triumph: after all, Twain’s famous pen name first appeared in its pages. If Twain inspired pride among his friends, he also found forgiveness among his enemies. During his stay in Virginia City, he received an invitation to lecture in nearby Carson City. The letter was signed by more than a hundred leading citizens—including two husbands of the Sanitary Commission ladies whom Twain had wounded with his miscegenation hoax back in 1864. He heartily accepted, and atoned for his past wickedness before a roaring crowd at the Carson Theater.

Back in San Francisco on November 13, Twain was as popular as ever—and as poor. He wanted to go East but couldn’t afford to. His creditors claimed most of his profits from the tour, and when he performed at Platt’s Music Hall on November 16, the city courts demanded a share of the proceeds in payment of an old debt: the bail bond he had signed for Steve Gillis two years earlier. Adding to his frustration, his second lecture fizzled. He incorporated new material that pushed the bounds of propriety, and told jokes too vulgar to “be heartily laughed at by ladies,” observed the Dramatic Chronicle. That “coarseness” noted by Harte had gotten out of hand; if he wasn’t careful, he might squander his soaring reputation.

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Fortunately, he soon found the solution to his financial woes. While never a brilliant businessman, he had a knack for negotiation. He had convinced the Sacramento Union to send him to Hawaii, and now he persuaded another big paper, the Alta California, to give him an even broader assignment. He would be its “traveling correspondent,” a commission he hoped would carry him through Europe, Asia, and beyond. He would take a steamer to New York, pitch his Hawaii book to a publisher, ride his rising star to greater fame in the East, and plan his pilgrimage around the world. But first, he would say good-bye to San Francisco.

On the evening of December 10, Twain delivered one last lecture. This time he repeated his original talk from October, and met with vociferous approval. He concluded with a sincere farewell to the city he loved. He praised its generosity, its “good-fellowship.” After five years in the Far West, he confessed his qualms about returning East. The country he once knew had become an “unknown land,” wasted by war, dotted with premature graves. Time never stood still, and it wouldn’t in California either. In his absence, he expected the state to continue its rapid ascent. Channeling the rhetoric of Thomas Hart Benton and legions of local boosters, Twain waxed lyrical about California’s prospects. “She stands in the center of the grand highway of the nations,” he declared. “[S]he stands midway between the Old World and the New, and both shall pay her tribute.” The approaching transcontinental railroad would unite East with West, connect the traders of Europe with the raw riches of Asia, and bless California with a boundless prosperity and population. “Has any other State so brilliant a future? Has any other city a future like San Francisco?”

Five days later, he departed for New York aboard the steamship America. He left behind more friends “than any newspaper man that ever sailed out of the Golden Gate,” he wrote his family wistfully. Never again would he find such a “fraternity” of young writers like Harte and Stoddard—yet he would remain close to both men, and indissolubly linked to the city that had lifted him to literary greatness. In a few short years, San Francisco had honed the Washoe Giant into a writer of exceptional intensity. By the time he went East in 1866, all the colors of his palette were in place: the slashing wit, the moral urgency, the comic realism. He would be returning to a nation in desperate need of new voices. The country was in flux. The Civil War had unglued it from its past; in the years that followed, a fast-growing industrial economy sped it toward a bewildering future. In the midst of this came an outsider from the West to help America find its footing, a folk artist of improbable talent and originality who became, in the words of William Dean Howells, the “Lincoln of our literature.”

Excerpted from "The Bohemians: Mark Twain and the San Francisco Writers Who Reinvented American Literature." Reprinted by arrangement with The Penguin Press, a member of Penguin Group (USA) LLC, A Penguin Random House Company. Copyright © 2014, Ben Tarnoff.