Ah, roleplaying. For some, it is THE reason they play tabletop rpgs. For others, its the complete and total BS that happens between combats. Roleplaying comes to some groups naturally, but definitely not to others. At some point, I’d like to gather every resource I’ve ever read on roleplaying at the table and distill some of the salient points into some kind of easy, quick hitting package that a GM can just pick up if he or she wants to kickstart that part of their sessions. Because I truly believe that even the most hardcore, optimizing, meta-thinking tables can be encouraged to do some sort of roleplaying. Whether its the role playing the DM wants is another question, but at least that table can be coaxed in a certain way.
The short answer to good roleplaying is that is comes from two sources: 1) somewhat developed and interesting characters in 2) well-described and interesting environments. Imagine a dungeon corridor with two doors. One door shines brightly with from all the gold and treasure behind it, while one is shaking and the screams of a damsel can be heard from behind. Which door do the characters open? An adventurer that’s basically a bag of hit points with a sword won’t really care. But for a player that’s put a hair of thought into his/ her PC, they might react one way or the other, depending on what kind of character they built. Roleplaying and player choice kind of dovetail with one another.
In terms of developing their characters, I find that a lot of players associate roleplaying with having a thick, Shakepearean backstory, and they quickly conclude that they can’t be bothered. There’s nothing wrong with the novella-length backstory, but that’s not the only way to develop a character. Back in the 3e days, Dungeon magazine ran a piece called the Seven Sentence NPC that I’ve used to this day. Just have the PCs fill it out as simply as they possibly can, and see what happens.
1) Physical Description: My PC wears a brown hunting outfit and carried a shotgun. He also has a gigantic head.
2) Attributes: He is dextrous enough to make a living as a hunter, but he’s really dumb.
3) Useful knowledge and skills: He knows about natural stuff.
4) History and/ or Occupation: He hunts wabbits.
5) Values and Motivations: He wants to get that darn wabbit.
6) Personality/ Interaction with Others: He is very focused on his job, and very shy around the ladies.
7) Distinguishing Characteristic: He stutters.
If the players can’t match the roleplaying depth of this guy, then something’s wrong.