What makes The Woobie work
There are a variety of factors that lead to a character we consider The Woobie.
- Frequent or Continuous Suffering: It's clear that the suffering the character goes through should be one of these, the former more commonly for serial and the latter more commonly for standalone works. Characters who are one-shot or infrequent recurring characters in serial works would more likely follow the "continuous" rule. Basically, frequency is when you add up all the events or even all the major bad events, and they add up to something huge, while continuity is where the suffering is the status quo. It is certainly possible to have both at once. Of course, this alone is not very different from a regular Butt-Monkey.
- External Circumstances: A character who suffers as a result of their own actions is not a Woobie. So, for example, if a character has to live with the consequences of doing something bad (such as cheating) or stupid, provided they were warned, (such as charging right into a dangerous battle), they are not a Woobie.
- Important Note: Being too afraid, weak, or self-defeating to prevent someone from hurting you is different from causing your own problems. Not only are all of these flaws sympathetic enough that they add to Woobie status rather than subtracting from it, but the flaws themselves may have been caused by the same or other attackers in the first place indirectly, especially if they are highly influential like Abusive Parents.
- Powerlessness: The best Woobies tend to be characters without any power, such as someone discriminated against by everyone else, children in abusive families, underlings always on the edge of losing their job, or characters who always fall victim to bad luck no matter what they do. Too much power (such as being a strong matriarch, or able to outwit authority figures) diminishes the sympathy since the audience is sure they can take care of themselves. Sympathetic flaws like weakness (physical or emotional), self-defeating behavior, and proneness to emotions such as sadness and anxiety over ones like excitement and anger will not usually make the status on their own, but can be hugely beneficial in pushing a questionable character over the line (think of them like condiments; they don't themselves make a meal, but they can add flavor to one). A character who is extremely virtuous—kind, honest, loyal, etc.—who also suffers heavily is also a more likely Woobie than one who isn't.
- For Jerkass Woobies: The "Just Deserts" Test: A character who is actively cruel to others cannot be a regular Woobie by default. What differentiates a Jerkass Woobie from a regular Jerkass is how well their suffering justifies their actions or vice versa. This is often a matter of opinion, especially when the Designated Monkey reaction is involved. If the suffering does not justify the actions ("Just because X happened to you doesn't mean you can do Y!") or the actions justify the suffering ("You deserve to have X happen to you because you did Y!"), the character in question is probably not a Jerkass Woobie. On the other hand, if the actions do not justify the suffering ("They may have done Y, but don't you think X happening to them are a little harsh?") or the suffering justifies the actions ("X happened to them, and they were so unhappy about it that they started doing Y."), they probably are. The suffering chart◊ meme can be useful here. Generally if a character's "deserve it" is between 40-80 and their suffering is a 60 or higher they qualify, but if a character is a 90 or above they can risk being so terrible that their suffering is outweighed by their heinousness.
Audience Reaction side
What seems a little tricky about this is the idea that the fandom feels sorry for the character. Now, unless the show is a Sugar Bowl (or, for a particularly unlucky Woobie, a Sugar Bowl except for this one guy's bad life), and sometimes even then, the audience will feel sorry for most if not all of the characters at one point or another. People have specified feeling sorry for the resident Jerkass in the episode they were watching only. Clearly, this alone is not enough to make the character a Woobie. So what is the difference?
The answer lies mainly in whether or not the suffering and/or the toll it takes is tough to undo or even outright unfixable.
Consider the following scenario: Alice has lots of great friends, while Bob has never had any despite trying to make them for years. Then, one day, Alice loses all her friends due to a misunderstanding. Seeing an opportunity, Bob tries to befriend Alice's friends himself, but they are put off by his poor social skills and long history of having no friends. The end result is that while Alice eventually reconciles with her friends at the end of the episode, Bob still doesn't get any friends of his own.
Now, when the audience is watching Alice, they would likely say something to the effect of "I felt bad for Alice when..." When the topic turns to Bob, the audience members would likely say something closer to "I feel sorry for Bob because..."
The main difference between these two is the conditionality of the sympathy, exemplified in the different tenses for "feel". For Alice, the tense is past, meaning the sympathy is conditional—it's fleeting, temporal, in the moment; their sympathy for her lasts only as long as her situation is negative, and it ends when she returns to the more positive status quo. Conversely, for Bob, the tense is present, meaning ongoing and unconditional—consistent, steadfast, forever; his situation was negative from the get-go and remains that way throughout the story thanks to both a character flaw that can't be easily fixed and a history that can't be changed at all, thus ensuring the audience continues to feel for him.
Another important factor is whether it's personalized. Suppose your show takes place during a great war and plenty of hardships are had by everyone. They can't all be Woobies, but what about the one who went through a succession of abusive parents and then nearly died due to ostracism? This is heavy suffering even for the universe (think Crapsack Only by Comparison, but with characters instead of worlds), and so the character stands out even in one of the bleaker worlds. This can also be apparent in a Crapsack World wherein only a limited number of characters are sympathetic.
Uses for a Woobie
One potential use for a Woobie is making other characters look evil. Villains who attack the hero are just trying to win their fight. Villains who attack The Woobie are cowards at best, and bullying monsters at worst. Oh, and if the character is the primary reason another is The Woobie? They'll most likely be hated, perhaps in a good way, though this is often the intended response.
Another is to provide a tragic contrast; kind of a weird opposite of comic relief. And of course, sometimes they're used just to show how messed up the world is as a whole. Some are intended to be in-universe Woobies, particularly Littlest Cancer Patients like Tiny Tim (who, in a surprisingly effective way, had a curable illness), in order to tug at the heartstrings of other characters as well as the audience. Unfortunately, sometimes, this will lead to the character becoming a Sympathetic Sue, or just to Too Bleak, Stopped Caring.
Avoiding Too Bleak, Stopped Caring
Generally speaking, piling loads of crap onto the character will turn them into The Woobie, particularly if they have traits such as kindness, a large number of sympathetic flaws, and powerlessness. But at some point, there's just too much. So how do we find that balance of creating a good Woobie without also getting Too Bleak, Stopped Caring and Sympathetic Sue accusations?
The most important rule is Show, Don't Tell. It's practically Rule #1 of writing in general, but in the specific case of the Woobie, it accomplishes a few things: Since we see bad things happen, we understand they're plausible for the universe. Another thing that's helpful is seeing how much it hurts. Another piece of advice is to use tragic backstory sparingly. Tragic backstory is great for making a character The Woobie quickly, but it has to have some lasting effects; (unfixable suffering, remember?) otherwise, it comes across as the author's refusal to put the character through hell, while insisting that they have done so anyway. Sometimes tragic backstory can be used to make a character who would have been a Woobie regardless even more of a Woobie. For instance, if your character is saying that today is the best day they're ever had, and even that day is punctuated by obviously pitiful moments, that character will almost certainly become a Woobie.
One issue with Sympathetic Sues is that they almost always violate Show, Don't Tell. At some point, whining about backstory gets old. Show some substance in the moment, and you should get the desired result.
Another potentially helpful device to avoid Too Bleak, Stopped Caring is to give your Woobie a happy ending and/or throw them a bone or two along the way. This way, despite the audience wanting to comfort this poor, innocent character, they'll be aware the writer is on the character's side, and as a result see the suffering with pure sympathy rather than frustration. This is especially helpful in serial/episodic works that last a long time.