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Anvilicious: "The Guilty Party", which states that an upbringing in ghetto-type places, coupled with having parents who are abusive or just plain neglectful, will lead you down a less-than savory path.
Values Dissonance: A Harlem Tragedy is about a woman being proud of her abuse at her husband's hands, because she says it shows how he's interested in her and how he always buys her things to make up for it later. Of course, given the generally satirical tone of the story, this probably isn't meant to be taken seriously.
Also, O. Henry was racist. Really racist. So racist as to make a "comical" reference to dousing black people in gasoline and burning them to death (although the term he used wasn't "black.")
Tear Jerker: Most of his stories are humorous, but some, most prominently The Last Leaf and The Furnished Room, are quite tragic.
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