YMMV / O. Henry

• 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.
• Heartwarming Moments: At the end of "A Retrieved Reformation", a cop is able to positively identify a notorious safecracker who he has been chasing. However, observing that said safecracker was willing to sacrifice his freedom by using his abilities to rescue a little girl, he pretends not to recognize him.
  • Also the final line of "The Last Leaf", when Sue pieces together why old Mike Behrman had caught pneumonia.
    Sue: Look out the window, dear, at the last leaf on the wall. Didn’t you wonder why it never moved when the wind was blowing? Oh, my dear, it is Behrman’s great masterpiece — he painted it there the night that the last leaf fell.
• Tear Jerker: Most of his stories are humorous, but some, most prominently The Last Leaf and The Furnished Room, are quite tragic.
• Values Dissonance:
  • A Harlem Tragedy is about a woman being proud of her abuse at her husband's hands, because it shows that he's interested in her, and that he's overpoweringly strong and masculine, and he always apologizes later and buys her things as an apology. Her friend, whose husband is much more meek and compliant, feels terribly jealous. It's clearly intended as satire, but still.
  • His racial attitudes can be sometimes particularly jarring, because they're usually not immediately relevant to the story, so they're not expected when they appear. For instance, an out-of-work match salesman in one of his minor stories talks about how gasoline is so much better for setting black people on fire (and the word he uses is not "black"). Still, his attitude towards black characters was actually quite Fair for Its Day (although with lots of patronizing attitudes and Uncle Tom Foolery - which can be genuinely jarring for today's readers.) In the above mentioned short story, the protagonist is a Snake Oil Salesman/petty Lovable Rogue who seems to be almost an Ineffectual Sympathetic Villain, when compared to the Deep South regular folks who were buying his 'patent instantaneous fire kindler' before they 'stroke oil', which got him out of his business.