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Clearly a man who likes his twist endings.
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William Sydney Porter (September 11, 1862 – June 5, 1910), Pen Name O. Henry, is an American writer of chiefly short fiction (the most famous piece being "The Gift of the Magi") and one novel (Cabbages and Kings). His stories are famous for their Mandatory Twist Endings, warm characterization and wit.

For some inexplicable reason—at least partially having to do with two film adaptations, which are quite good—he is most popular in the former USSR republics, where phrases such as "Bolivar cannot carry double" have become stock quotes.

The "Oh Henry!" candy bar (later associated with Hank Aaron) was partly named in homage to him. (And partly named for a boy who flirted with the girls at the candy factory.)


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Works by O. Henry with their own trope pages include:

Other works by O. Henry provide examples of:

  • Ambiguously Gay: In "The Last Leaf," it's implied about as strongly as possible for a 1907 story that Sue and Johnsy are lesbian lovers. They are artists in Greenwich Village (even then a Gayborhood), they have affectionate nicknames for each other (and Joanna has the masculine nickname of "Johnsy"), they call each other "darling", and Sue snorts with derision when the doctor suggests that a man might be the cause of Johnsy's despair.
    • The film version inserts a failed love affair as part of the reason for Johnsy's collapse, probably so people wouldn't think they were together (good luck with that).
  • Asshole Victim: Wentworth Caswell in "A Municipal Report", Mr Conyers in "The Atavism of John Tom Little Bear", and Rob Chandler in "The Marionettes", all of whom are abusive husbands. Played with in "The Last of the Troubadours", as King James had actually changed his mind on finding out that Ellison was related to him and was willing to go into business with Ellison, but Sam - the troubadour - isn't aware of this and shoots him dead.
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  • Balloon Belly: Poor Stuffy Pete in "Two Thanksgiving Day Gentlemen," after he guilt-trips himself into eating two huge Thanksgiving dinners in immediate succession provided by mutually unaware benefactors:
    "Around the first corner Stuffy turned, and stood for one minute. Then he seemed to puff out his rags as an owl puffs out his feathers, and fell to the sidewalk like a sunstricken horse."
  • Banana Republic: Cabbages and Kings is the Trope Namer. Its stories are set in the fictitious Latin American country of Anchuria. The phrase "banana republic" appears in the story "The Admiral" and soon after acquired its catch-all term status for such countries.
  • Beleaguered Childhood Friend: In "After 20 Years," two childhood friends Jimmy Wells and Bob part ways and agree to meet at the same spot two decades on. Jimmy, who is now a wanted criminal, arrives at the same spot only to be questioned by a policeman, who moves along. Another detective shows up shortly after, passes himself off as Bob, and arrests Jimmy; in a twist, it is revealed that the first policeman was actually Bob, who didn't have the heart to arrest Jimmy and sent a colleague to do so instead.
  • Big Applesauce: A popular setting of many of his stories; the short story collections The Four Million and The Trimmed Lamp are set there.
  • Bittersweet Ending: "The Last Leaf" ends with Johnsy recovering from pneumonia, as seeing the titular leaf remain in place despite a raging storm gave her the will to pull through. However, said leaf was actually painted on by the elderly Behrman during the night, and he contracted - and eventually passed - from pneumonia himself, having finally painted his "masterpiece" that saved Johnsy's life.
  • Braids, Beads and Buckskins: John Tom Little Bear, a Native American who goes into business with Jeff Peters in "The Atavism of John Tom Little Bear". He plays the role of a stereotypical mystic Native American chief, but is actually a college graduate and a fluent English speaker. He reverts to type when the little boy they've been looking after is kidnapped by his abusive dad, not only reverting to broken English, but also hunting the dad down and scalping him.
  • Bratty Half-Pint: Johnny Dorset from "The Ransom of Red Chief." He makes his kidnappers strongly regret abducting him. The two crooks have to pay Johnny's parents to take him off their hands.
  • Can't Get in Trouble for Nuthin': In "The Cop and the Anthem," the protagonist Soapy tries to get himself arrested so he can spend the winter in a warm jail cell. He tries everything from vandalism to petty theft to disturbing the peace with no success. The Twist Ending of this short story shows Soapy deciding to reform and find a job, only to be arrested for vagrancy right when he decides on his Heel–Face Turn.
  • Chekhov's Gun: Two in "A Municipal Report", a taxi driver's coat and a torn dollar bill. They allow the narrator to make the connection between the taxi driver, the writer he has come to interview, and the irritating drunk man he meets in the hotel, who turns out to be the writer's husband - and is abusive and steals her money.
  • Con Man: Jeff Peters and Andy Tucker, protagonists in several stories, make their living this way. They appear most notably in the collection The Gentle Grafter.
  • Cowboy: Normally of the working cowboy variety, protagonists in many stories.
  • Corrupt Corporate Executive: An early example in "Shark" Dodson from "The Roads We Take."
  • Deadly Doctor: "The Marionettes" features one, though in his case, it turns out to be a good thing. The doctor is also a burglar and safecracker. His patient turns out to be an abusive husband who has been depriving his wife of money, and after killing the husband, the doctor gives the safe combination to the wife, puts money he has stolen from another job in the safe and claims that the husband has left her the money inside as a parting gift.
  • Domestic Abuse: "A Harlem Tragedy," which, despite its title and its now politically-incorrect subject matter of spousal abuse presented as love, is a very light-hearted story.
  • Downer Ending: Occasionally, for example in "The Furnished Room" and "The Last of the Troubadours."
  • Driven to Suicide: A particularly dark example of this in "The Furnished Room." The woman the protagonist was looking for killed herself in said room - a fact the landlady covered up - and he also gasses himself to death there.
  • Dying Moment of Awesome: "The Last Leaf" sees old Behrman die of pneumonia, having finally painted his masterpiece - the titular ivy leaf that gave the young Sue the will to pull through her own bout of pneumonia.
  • Even Evil Has Standards: "The Tempered Wind." Two conmen, Parleyvoo Pickens (the narrator) and Buckingham Skinner, team up with a third conman and set up a business in New York selling fake bonds. However, a newspaper report exposes the business as fake, and the conmen get a nasty surprise when their customers show up at the office and are revealed to be poor factory workers, disabled war veterans, old women, and even children. One woman tells them about how she had invested all her life savings and needs the money back for her dying child, while the factory girls are losing money for missing work, and one women is in tears because she was saving for her wedding. Pickens and Skinner give all the money back. When the reporter who wrote the article interviews the conmen again, Skinner says:
    Me and Pick ain't Wall Streeters like you know 'em. We never allowed to swindle sick old women and working girls and take nickels off of kids. In the lines of graft we've worked we took money from the people the Lord made to be buncoed — sports and rounders and smart Alecks and street crowds, that always have a few dollars to throw away, and farmers that wouldn't ever be happy if the grafters didn't come around and play with 'em when they sold their crops. We never cared to fish for the kind of suckers that bite here. No, sir. We got too much respect for the profession and for ourselves.
    • A lesser-known O. Henry short story, "An Unfinished Story," used this to create the author's trademark Twist Ending. On Judgment Day, the narrator sees a long line of men waiting to go to Hell. Then the reader hears a sad story about a shop girl who only earns $5 a week. The story goes into details about her budget, how she sometimes goes hungry without anyone noticing, etc. She's about to accept a date from a rich man who has a taste for shop girls (whether he's a Romeo pimp or just likes to have kept women is not specified), but changes her mind at the last moment. The narrator says her story won't end until a night when she's feeling a little hungrier. Meanwhile, an angel tells the narrator that the long line of men are store owners who only paid their shop girls $5 a week, and asks "Do you belong with them?" "Not on your immortality," the narrator replies indignantly, "I only burned an orphanage and robbed a church!"
    • Dr James in "The Marionettes" might be a burglar, but he draws the line at beating women.
  • Exasperated Perp: In "The Ransom of Red Chief," the kidnapped Bratty Half-Pint exasperates his incompetent abductors so much that they're willing to pay the child's father a ransom to take the youngster off their hands.
  • Flash Sideways: "The Roads We Take" starts as the story of a ruthless criminal who wonders what his life would have been like if he hadn't come West — then he wakes up, and from then on it's the story of a ruthless businessman who dreamed about what his life would have been like if he hadn't come East.
  • Genre Shift: "Roads of Destiny", which is set in 18th century France and, unusually for Henry, does not contain any slang.
  • Gold Digger: Nancy and Lou in "The Trimmed Lamp." Lou works in a laundry, while Nancy works in a high-end department store with rich customers, whose style and mannerisms she imitates. Both live in hope of bagging a rich man, especially Nancy, as she earns less than Lou (which Lou keeps rubbing in her face). Lou ends up with a rich man - but her boyfriend Dan leaves her for Nancy.
  • Ill Girl: In "The Last Leaf," Johnsy is seriously ill with pneumonia, but recovers eventually.
  • Ineffectual Sympathetic Villain: "The Ransom of Red Chief." The two kidnappers are stupid small-time crooks who prove no match for the Bratty Half-Pint they abscond with.
  • The Irish Mob / Officer O'Hara: As many of the stories are set in New York in the late 19th/early 20th century, there are plenty of examples of both. "The Coming-Out of Maggie," for instance, involves an Irish-American gang and their girlfriends going to a dance. The titular Maggie's date, Terry O'Sullivan, turns out to be an Italian mobster called Tony, who she pretends is Irish as she's sick of never having a date for the dances. Unfortunately, his cover is blown when the gang leader's captain in the police force has no idea who 'Terry' is.
  • Let Off by the Detective: Happens in "A Retrieved Reformation." Wanted safecracker Jimmy Valentine, being hunted by detective Ben Price, changes his name and gives up his life of crime to marry and get a legitimate job. Eventually, Ben tracks Jimmy down, but before he can arrest him, Jimmy's niece locks herself in a bank safe. Jimmy breaks it open to rescue the girl while Ben looks on, revealing his identity — but the Twist Ending sees Ben refuse to arrest Jimmy when he turns himself over, acting as if he doesn't recognize him and letting him go.
  • Love Triangle: The subject of "The Hypotheses of Failure". A divorce lawyer sees three clients in a row, who are all involved in the same case: a woman is unsatisfied with her husband and has left him in pursuit of another man. The lawyer sees the other man first, then the woman, and then the woman's husband. Or so he thinks. The first man is actually the husband, who is willing to grant his wife a divorce. The second man is the other man in the relationship, who sees the woman as an Abhorrent Admirer and is desperate to get rid of her.
    • In "The Love-Philtre of Ikey Schoenstein", both Ikey, a pharmacist, and his friend Chunk McGowan are in love with the same woman, Rosy Riddle. Chunk asks Ikey for an aphrodisiac for Rosy as he wants to elope with her and worries she might get cold feet, but Ikey gives him a sleeping powder instead and tips her father off. Unfortunately, Chunk has a change of heart, decides to woo Rosy by honest means and - to Ikey's horror - puts the sleeping powder in Rosy's father's drink instead.
  • Meaningful Echo: In "The Roads We Take", the paragraph about Dodson revealing his true nature is repeated word for word when the other Dodson turns out to be not so different.
  • Mister Muffykins: "Ulysses and the Dogman" and "Memoirs of a Yellow Dog" both feature one. In the former case, the hero is a Henpecked Husband whose wife cares more about their horrible little dog than him. After meeting an old friend from the Wild West, he ditches both his wife and the dog and heads to Colorado with his friend. In the latter case, the dog is the narrator, and he and his owner skip town and the owner renames him Pete, much to the dog's joy.
  • Mock Millionaire: "Transients In Arcadia"; "The Policeman O'Roon"; "While the Auto Waits" although the man in the story, who Henry leads us to believe is of a lower class than the woman, is actually a millionaire, or at least very rich, while she is pretending to be rich but actually works on the till of a cheap restaurant.
  • Nice Job Breaking It, Hero!: "The Last of the Troubadours."
    • In "Witches' Loaves", a woman who owns a bakery has a regular customer who buys stale bread and feels sorry for him, thinking he must be starving, so she makes a hole in a loaf of bread and puts some butter in it before selling it to him. The man is furious because he had been designing a building for a competition and using stale breadcrumbs as a type of eraser. Thanks to the buttered bread, his drawing is now ruined.
  • No Name Given: According to the writer himself, the "O" stands for "Olivier" — some of the author's early stories use the pen name "Olivier Henry." By 1902, the shortened version became his preferred pseudonym.
  • Old Retainer: Several stories feature one, usually a devoted former slave, such as Uncle Bushrod in "The Guardian of the Accolade", and Uncle Caesar in "A Municipal Report" (a particularly dark example, as he murders the abusive husband of his former mistress.)
  • Pity the Kidnapper: Trope Codifier. In "The Ransom of Red Chief," two stupid small-time criminals kidnap a Bratty Half-Pint who proves to be so insufferable that the kidnappers end up paying a ransom to his father to take him back.
  • Punny Name: William Pry and Violet Seymour, a pair of ghoulish gawkers or 'rubberers' in "A Comedy in Rubber".
  • Replacement Goldfish: In "A Double-Dyed Deceiver", the Llano Kid acts as this for a grieving mother whose son is missing, as part of a plot with the local US consul to steal a load of money from the family safe. He ends up warming to his new 'mother' so much that he ultimately decides to stay behind and live as her son, and threatens to kill the consul if he makes trouble. It also turns out to be a case of Kill and Replace, because the reason why he's in the area in the first place is because he killed a man in a bar fight and skipped town. And the man he killed? The missing son.
  • Stupid Crooks: The inept kidnappers in "The Ransom of Red Chief." They're dumb enough to kidnap an obviously evil child, and he's such a terror that they end up having to pay his father to take him back.
  • That Man Is Dead: "A Retrieved Reformation," in a way. When wanted safecracker Jimmy Valentine gives up his life of crime to go straight and get married, he changes his name to Ralph D. Spencer.
  • Title Drop: In "The Roads We Take," the protagonist wonders if he'd have turned out a different man if he'd made a key choice differently, and his colleague says "I reckon you'd have ended up about the same... It ain't the roads we take; it's what's inside of us that makes us turn out the way we do." The end of the story bears him out.
  • Tomato Surprise: "After 20 Years" has the revelation that the main character is an infamous criminal and his friend is a policeman.
  • Took a Level in Badass: Willie Robbins in "The Moment of Victory". He is so incensed at a rude comment from a woman that he signs up to fight in the Spanish-American War and goes from a meek little guy into a Blood Knight.
  • Train Job: "The Roads We Take" opens with a trio of Wild West desperados hijacking a train when it stops to take on water.
  • Twist Ending: The author used this device so often that he serves as the Trope Codifier.
  • Villain Protagonist: Because O. Henry spent time in jail, many of his stories, like "The Ransom of Red Chief," focus on (relatively) petty criminals.
  • Wild West: Another of the author's popular story settings, usually limited to Texas ranches.

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