I think there's nothing wrong with playing an evil character as long as others are also evil. It's quite the same as if all the party was evil except for the paladin within the group, it just doesn't fit. Everybody should give their input before the campaign/game as which type of game they want to play, and after that play accordingly with what the group has decided, with of course some personal input but not too extremely far from what has been decided...
To some extent, yes. But newbies should stick with generally heroic PC's.
Later, a group of experienced and MATURE players can try a all evil game for a break.
Been a long time since I made this thread, several months in fact. Just giving you guys an update:
He's gotten his act together, for the most part. We're starting a new campaign, in which he's playing a CN Dwarven Cleric of Gorum. While his character loves fighting, he's not overblown with it.
His attitude changed after he went to the Black Market to fence some potions he stole from an alchemist. The alchemist was selling illegal potions and drugs at the Black Market and spotted my brother's Fighter. The Alchemist happened to be a high ranking member in one of the gangs, so my brother's character 'vanished', that Fighter is currently sleeping with the fishes. I was disappointed that I had to result in doing a character death to get my point across, but he refused to listen to me up until that point.
I'm letting him play in the new campaign since I feel that he's learned his lesson and wont go overboard with his actions.
I hope you post another update after a session or two. :) Since you didn't mention it, I assume he didn't rage-quit after losing his fighter. Did he have a chance to role play the scene, or was it just flavor text for, "You're dead now."