A "woobie" is a name for any type of characters who make you feel extremely sorry for them. Basically, the first thing you think to say when you see the woobie is: "Aw, poor baby!" Woobification of a character is a curious, audience-driven phenomenon, sometimes divorced from the character's canonical morality. And while it's technically a YMMV trope, it's hardly tough to spot the guy the writers intend them to be, considering all the bad stuff that tends to happen to them.
A story with the Woobie allows the audience to vicariously experience relief from some pain by fantasizing about relieving the Woobie's pain. (No, not that way! Well, okay, sometimes.) Woobification can also tie into a disturbing hurt/comfort dynamic, in which fans enjoy seeing the Woobie tortured so they can wish the hurt away. This is often explored in Hurt/Comfort Fic.
An important aspect of the Woobie is that their suffering must be caused by external sources. A character who suffers as the result of their own actions is a Tragic Hero and does not qualify.
The difference between the Woobie and such Sickeningly Sweet characters as the Littlest Cancer Patient is that the audience actually finds the Woobie compelling rather than pathetic. Where you draw the line is sometimes a matter of opinion.
Sometimes a Woobie goes Omnicidal Maniac and seeks to destroy the world in a bid to make the pain stop, in which case you're dealing with a Woobie, Destroyer of Worlds. Sometimes it's possible to bring such a woobie back from the edge, but other times, only his or her destruction in a Shoot the Dog moment will stop things.
In many versions there is also something about the Woobie's suffering that is notably heroic or noble. In this case the character is an Iron Woobie. When the Woobie does not show much outward emotion about their hurts (or anything else, for that matter), they are a Stoic Woobie.
In anime, the Woobie makes up a large part of Moe characters. Part of their appeal can come from them constantly striving against their chains. Can be taken to the point of Break the Cutie, and if the amount of misfortune seems too great it may result in Deus Angst Machina.
If the character is The Chew Toy, a Jerkass, or a Hate Sink, he is not the Woobie (unless the character is also meant to be sympathetic). If the character doesn't let bad events faze him, he is not the Woobie. A small, one-off bad event does not make the character the Woobie, though it may qualify as a Tear Jerker.
If in your opinion the character desperately needs to die, that's likely Damsel Scrappy. Should not ever be confused with Butt-Monkey. However, a Butt Monkey can often become a Woobie if abused too mercilessly.
For the curious, the fanspeak term "woobie" is ultimately derived from a word for a blanket, stuffed animal, or other soft object that a child keeps for its comforting properties (hence the name—some of these characters really could use a snuggling!).
Check out our analysis page on this trope if you're looking to write a Woobie of your own.
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