What is it about the brooding hero struggling with addiction that draws our interest so? What makes the character battling his inner demons so much more intriguing to know about than the well-adjusted hero?

For me, there's a little niggling part of me that likes to see obviously flawed individuals perform so spectacularly. We each have our own demons and our own vices that can damage our own views of ourselves, and knowing that our flawed characters can overcome these challenges can sometimes spark the confidence within us that we, too, can overcome our own flaws to accomplish something great. These sorts of negative inclusions to our characters can take several different flavors, but they all can help you understand more about your players.

For players that tend to prefer the darker aspects of roleplaying, this can sometimes take a rebellious nature. Creating characters that are both heroic and heavily flawed is kind of like throwing the middle finger to society. "Yeah, I shoot heroin, but I'm the only one who can save us from the Zombie Invasion, and you got disemboweled in your minivan, you soccer-mom slut."

This sort of player is easy to identify. Generally grungy and constantly defying convention for the sake of defying convention, what turns him on about his character flaws is that he is reinforcing his belief that that either society is wrong about his vice of choice, or that he can succeed when many believe he can't. These characters will often have the most crippling addictions or severe character flaws, as to enhance the mental victory they provide and to highlight the fact that these sorts of topics do not make the rebel uncomfortable.

When you encounter a player like this, you have a wonderful opportunity to enhance their gaming experience by having your in-world society actually look down upon him for his choices. As long as the critical good NPCs are more tolerant of him, the hero will take great pleasure in doing the impossible with the knowledge that everyone expects him to fail.

Many otherwise virtuous heroes will inexplicably have a non-personality related vice, such as a tobacco addiction or tendency towards rambunctious alcoholism. This is often a last-ditch effort by the player to nail on some sort of interesting quirk to their character, but these sorts of players often have no clue how to express themselves or show that their characters are interesting, too.

The vice itself is not an integral part of the character. It gives him something to do when he has no hook and needs to stay relevant. The key to engaging this character is presenting him (specifically) with situations where he can make a decision that reveals more about his character.

This sort of player doesn't know how to internally flesh out his character without external stimuli. With enough gentle prods, he will quickly develop a personality and be more self-confident with his social interactions, knowing that he has created a unique individual.

Keep in mind, it's also possible that your player added the vice to their character simply because it seemed like it fit and they are indeed merely using it to create an in-depth character. Sometimes, the little things really don't mean anything at all.

An interesting spin on the vice is when it falls on the BBEG's shoulders. Does he have a crippling addiction to dragonscale extract? Is he a compulsive gambler? An incurable womanizer? The party can use these flaws against the evil guy just as well as they could use the information that his fortress has a weak eastern wall.

Consider this; an Ocean's Eleven-style ploy where the party dupes the scepter of ultimate badassery from the antagonist by luring him into a dangerous gambling situation after the hottest female member of the party gets him deliriously drunk.

Don't forget the worst character flaw of them all; Pride! In a previous Darker DM Article, we discussed how the nicest and most holy-seeming individuals often could make excellent enemies - the inclusion of their insufferable pride and honor leaves this sort of trickery wide open. Darker PCs can taunt an insufferable paladin into a bad position by calling on his honor, and a dirty politician can't help but keep a good public image - I hear blackmail is a great way to learn more about his shadow government bosses.

Think about what negative character traits drive you and your enemies. Have you had any good encounters where your flaws got the best of you?