On Playing Evil - "So you want to be chaotic evil do you?"

One of the challenges which every GM will face is permitting his players to align themselves to darker forces.  Sometimes players have a romanticized version of what it would be like to be cut free from moral responsibility and go on a romp down darker paths.

I tend to look at playing evil a little differently in my campaigns.  It takes just as much; if not more work to truly roleplay an evil character and it should.  Consider the following;

1. Evil often can only achieve power in a vacuum of a greater evil. If you are a "lesser" evil your presence unless you are subservient will not be tolerated so your first opposition may be others of your ilk who simply do not play by the rules.

2. If there IS an absence of evil; then there usually is a well-entrenched force for good keeping it at bay.  Someone is taking a vested interest in keeping evil out and have systems in place to warn of their approach.  If evil is a weed then "good" is a gardner which leads to;

3. For evil to survive it must be subtle at the onset; anyone can wear their evil on a sleeve. That usually ends with you dying to the angry mob with pitchforks or tied to a post in the center of town surrounded by kindling. There is usually a reason evil moves by shadow or in the dark of night; it's to prevent the overzealous good majoirty from pummeling you.

It will take time for evil to sow corruption within this garden.  There are no lesser evil minions for you to exploit (good has plucked them before they could take seed as larger evil) so you often are on your own at first until you can foster small bits of corruption beneath the watchful eye of the tenders.

4. Corruption and power are two sides of the same coin. While simple power grab may be fun; corrupting good and turning it evil over time may be more satisfying and long lasting. Beat down that paladin and take his lands; you may simply make a martyr. Turn that paladin evil and creating a Lord Soth to take his place; now you have truly corrupted the landscape and made your mark and gained a powerful servant vice a resolute enemy (in the case where the paladin is simply driven away vice slain.)

5. Everyone is valuable in some way. Look at the mob; or warlords in Africa...Evil has a very extended family; You don't have to walk through town shooting old ladies and burning orphanages to be evil. True evil funds the orphanage, makes it the most recommend and well cared for in all the land, so you have an endless supply of children to experiment upon. True evil dines with the ladies auxiliary, paying for their meals, so they may use their bodies for cover when the righteous come with guns blazing to try and put you in the ground.

My advice;

Ask your players what are their vice; what is the "cardinal sin" that their character worships at the altar of; gluttony, lust, avarice, pride, despair, wrath, envy or sloth.

Challenge them to take each to new levels but make them fear the enemy as much as any first level fears an ogre.

Make "good" a palpable threat. Do not simply create a playground where evil goes unopposed and they will have a great time overcoming the challenges and creating their fiefdoms or lives of infamy.

When they cross the country side murdering, pillaging and conducting all sorts of villainy without fear; that loses one of the principle elements of evil.  Fear.

There is always someone stronger.  There is always someone who replace you.  You cannot trust your lover, your ally, your henchmen, your servant, your guard, your bloodbeast chained to the eternal stone of damnation in the well of suffering awaiting your virgin sacrfice to complete the ritual of transformation to abyssal godhood... oh and you definitly cannot trust the virgin either.

Like any game you want the players to have fun, too easy however, is not fun; make the players aware that alignment or morality does not make the world easier; it simply changes the opposition and the source of challenge.

For me this is when the fun begins.