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Classic Retelling
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144 Pages
Grade Level: 6-12

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Subcategories: Introduction, Complete Overview, Table of Contents

Tales of O.Henry Overview
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Time Line

1862-William Sidney Porter is born.

1883-Porter goes to Texas, where he works at a series of jobs and begins writing.

1887-He marries Athol Estes.

1896-Accused of stealing money from a bank, Porter flees to Central America. He returns to the United States when he hears that his wife is dying.

1897-Athol Porter dies.

1898-Porter is convicted and goes to jail. In prison, he begins writing under the pen name O. Henry.

1901-Porter is released from prison and wins acclaim as a short-story writer.

1904-Cabbages and Kings, a book of short stories set in Central America, is published.

1906-Porter writes "The Gift of the Magi" and "The Last Leaf." Both stories are instantly popular.

1908-1909-Several O. Henry short-story collections, including The Voice of the City, The Gentle Grafter, and Roads of Destiny, are published.

1908-1909-Porter writes "The Ransom of Red Chief." Shortly afterward, he dies penniless and alone.

Prison Life

William Sidney Porter spent more than three years in prison for the crime of embezzlement (stealing funds). Although his prison years were difficult, Porter was treated well, worked as a pharmacist, and used this time to gather information for his stories. He met prisoners and heard about crimes that he found fascinating. He learned about men who were lifelong criminals and men who longed to reform themselves. His stories, written under the name of O. Henry, describe these people with humor or irony, but always with some degree of respect. Interestingly, Porter did not write about his own prison experiences, although many people urged him to do so. "I will forget that I ever breathed behind these walls," he said, shortly before he was set free. For the rest of his life, he stayed true to his promise and never once wrote or spoke about his years in prison.

O. Henry's New York City

After leaving prison, Porter became a New Yorker. He moved to New York City in 1902 and lived there for the rest of his life, basing many of his stories there. His best known works are set in New York. He used the city as the basis for a group of Arabian Nights stories and, in some of them, calls New York "Baghdad-on-the-Subway." He used this term to link modern New York in his readers' imaginations with the exotic settings of The Arabian Nights, a collection of romantic and magical stories set in ancient Baghdad, a city in Iraq.

Porter loved New York City. He was fascinated by the shops, the nightlife, and the bustle of the busy streets. He also loved the glamour. At the height of his popularity, Porter could dine in the fanciest restaurants and buy tickets for the most popular shows. Yet he never lost sight of the fact that there were thousands of working-class New Yorkers who lived very differently. Even when his life was very successful, he kept an eye on the "common folk" and wrote about the "four million" New Yorkers that other writers tended to ignore.

Later, when his expensive tastes led to bankruptcy, Porter found himself among the common folk again. Perhaps this is the reason he was able to write so effectively about both sides of New York City life. He had dined in the houses of the rich and had lived in the low-rent apartments of the working class and the poor.

Porter loved New York because it was exciting. But he also loved the city for another reason. In this huge city, with its hundreds of thousands of people, he felt safe at last. He stopped worrying that his past would catch up to him and certainly never told anyone about his time in jail. He built a reputation as O. Henry and was able to leave William Sidney Porter behind him forever.

O. Henry's Stories

Story Structure

Porter's first biographer, C. Alphonso Smith, pointed out in O. Henry Biography (1916) that O. Henry's stories had four stages. In the first stage, O. Henry gets the reader's attention with a striking opening situation, called "the arresting beginning." Exposition takes place at this stage. In the second stage, the rising action, the reader begins to guess the story's ending. In the third stage, the climax, the reader learns that he or she was wrong about the ending. In the fourth stage, the falling action, the story concludes. The ending is triumphant with a surprise involving sudden suspense. This is the story's resolution.

Story Elements

O. Henry's stories were written to help people escape from their everyday problems. The author had been a skilled storyteller since he was a teenager. He used to entertain people in his uncle's drugstore and on the Texas ranch where he lived as a young man. He wanted his stories to be entertaining and enjoyable. To achieve this, he uses lively dialogue, vivid and quickly drawn descriptions, humor, irony, chance happenings, and surprise endings.

In 1908 critic Henry James Forman wrote that "No talent could be more original or more delightful. The combination of technical excellence with whimsical, sparkling wit, abundant humor and a fertile invention is so rare that the reader is content without comparisons."

Humor and Irony

O. Henry had a good sense of humor and liked to depict ironic situations. Some of his stories, such as "The Ransom of Red Chief," are very funny throughout. Others deal with serious subjects and include only small amounts of humor.

Most of the humor in O. Henry's stories takes the form of irony. When an author uses a word or phrase to mean the exact opposite of its literal or normal meaning, it is called "irony." Sometimes, a whole situation is ironic. The author sets up a scene one way, and then the opposite of what you might expect actually happens. An example is when Plumer, the homeless man in "A Madison Square Arabian Night," discovers that he must teach some manners to a wealthy and well-respected man. "The Gift of the Magi" contains a plot twist that is a classic example of irony. Ironic coincidence best seen in "The Gift of the Magi" and "The Furnished Room."


O. Henry's plots often involve coincidence. Coincidence (chance or luck) also plays a key role in most of O. Henry's stories. Very often, the strange coincidences that the characters experience add another element of humor to the story. For example, in "After Twenty Years," two old friends make plans to meet. But one has just learned something about the other, and this leads to an unexpected event. In "A Retrieved Reformation," it is a coincidence that Ben Price happens to be watching at the exact moment that Jimmy decides to save a little girl. In these stories and others, the coincidence acts as a kind of warm-up to the story's surprise ending.

Surprise Endings

O. Henry's stories are perhaps best known for their surprise endings. A surprise at the end of the story can bring an enormous amount of pleasure to readers. The key to a surprise ending-and it is one that O. Henry mastered early on-is that it has to be believable. Consider, for example, the surprise endings in "The Last Leaf" and "The Third Ingredient." These endings are probably not what you predicted, but the outcome is reasonable in view of who the characters are. In other words, you can accept the endings of the stories as the mark of a good writer and know that O. Henry tricked you once again.


O. Henry (1862-1910)

O. Henry is the pen name of William Sidney Porter. Some critics say that he is one of the greatest short-story writers in American history.

Porter was born in Greensboro, North Carolina, on September 11, 1862. His father was Algernon Sidney Porter, a doctor, and his mother was Mary Jane Virginia Swain, graduate of a women's college. When Porter was three, his mother died. His father then failed financially and became an alcoholic. Porter grew up in the home of his aunt, a schoolteacher named Evalina Porter, a strict woman who educated Porter and promoted his interest in art, literature, and writing. At 15, Porter became an apprentice pharmacist in his uncle's drugstore, which also was a soda fountain, newsstand, and saloon. Young Porter liked to draw caricatures of customers and to regale them with stories and skits that he wrote himself. In 1881 he was licensed as a pharmacist.

A family friend who was a leader of the Texas Rangers invited Porter to visit his son's Texas ranches with him. Porter happily accepted and soon settled on one of the ranches, continuing to expand his reading and to entertain his hosts with his original stories and cartoons. Moving to Austin, Porter worked as a pharmacist, bookkeeper, clerk, and draftsman. In 1887 Porter eloped with 17-year-old Athol Estes, daughter of a wealthy Texas businessman. Her parents objected to the match because both Porter and Estes had tuberculosis.

The period from 1887 to 1891 was the happiest time in Porter's life. He and his young wife rented a tiny set of rooms and began thinking about starting a family. With his wife's support, Porter began to write stories for national magazines. Athol probably was the model for Della in "The Gift of the Magi," his most famous work. But their happiness was short-lived. Their first son died shortly after his birth in 1888 and their daughter Margaret's birth the next year almost killed Athol. Porter also lost his job in 1891 and began to work as a bank teller and bookkeeper.

In 1894 Porter resigned his bank job to start a humorous weekly magazine called The Rolling Stone, which he used as a vehicle for his cartoons and stories. When the magazine failed, he joined the Houston Post as a reporter, columnist, and cartoonist. To earn extra money, he also took a job as a bank teller. In 1896 Porter was accused of stealing about $5,000 from the bank. Porter-supported by co-workers-claimed to be innocent and a grand jury had ruled that there was insufficient evidence to indict him. However, Porter ran away to Honduras, a country in Central America, to hide out. There he met others, such as the outlaw Al Jennings, who had also fled from the United States. Eventually, Porter would write about many of them in his articles and stories. Jennings later wrote about Porter in Through the Shadows with O. Henry (1921).

After a year in Central America, Porter learned that his beloved wife was dying. Desperate to see her one more time, Porter returned to the United States and remained with her until her death in 1897. Then he turned himself in to the authorities. In a controversial jury trial, Porter was sentenced to five years in an Ohio penitentiary.

During his time in jail (April 1898 to July 1901), Porter worked as a druggist in the prison hospital. He began to write in earnest, hoping to earn enough money to support his young daughter. Because he didn't want readers to know that he was in prison, he used the pen name of O. Henry. His first story signed under this pen name was "Whistling Dick's Christmas Stocking," which appeared in McClure's Magazine in 1899.

Writing as O. Henry, Porter published 12 or more stories during this period. The characters in these and later stories were based on inmates he met or heard about while in jail. The most famous was Jimmy Connors, who appears as Jimmy Valentine in "A Retrieved Reformation," one of Porter's most popular stories, later the basis for a play. He also wrote stories based on experiences he'd had in Texas.

After three years, Porter was released from prison for good behavior. After a short reunion with his daughter and his wife's family, he took a writing contract for Ainslee's in New York City, a magazine that had published some of his work while he was in prison. To hide his criminal record, Porter began writing full time under the name O. Henry. He was a prolific and skillful writer by this time, producing stories at the rate of one each week. Several major magazines published his stories and many considered him the best short-story writer in America. Some of his most famous stories, including "The Gift of the Magi" and "The Last Leaf," are set in New York City. These stories and others earned him a reputation as a gifted storyteller. He had a remarkable talent for capturing both the beauty and the ugliness of New York City life. He was known in New York as a pleasant, kind man.

With each new story that he published, Porter's popularity grew. He published collections of stories such as Cabbages and Kings (1904), which deal with revolution and adventure in Latin America. Eventually, he had a following of loyal readers who eagerly anticipated each new O. Henry story. In spite of his successes and a second marriage in 1907, Porter spent money carelessly and became an alcoholic. His second wife left him in 1909. Hounded by creditors and suffering from cirrhosis of the liver, Porter died penniless and alone in 1910.


Cabbages and Kings (1904)
The Four Million (1906)
The Trimmed Lamp (1907)
Heart of the West (1907)
The Voice of the City (1908)
The Gentle Grafter (1908)
Roads of Destiny (1909)
Options (1909)
Strictly Business (1910)
Whirligigs (1910)
Let Me Feel Your Pulse (1910)
Sixes and Sevens (1911)
Rolling Stones (1912)
Waifs and Strays (1917)
Seven Odds and Ends, Poetry and Short Stories (1920)
O. Henryana (1920)
Letters to Lithopolis (1922)
Postscripts (1923)
O. Henry Encore (1939)
The Collected Works of O. Henry (2 vols., 1953)

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