It's really hard, actually, to write a story around a bad guy and make him someone you can relate to. Sin City did it fairly well, and in some ways I felt Payback was a good example of it done it fairly well.
GTA has always struggled with that. At first it was basically just an arcade game. You get plopped right in, no real characterization; just take these missions and do it. You're a bad guy, it doesn't matter what happens- do what you have to to complete the mission. As time has gone on they had to characterize the person you're playing and from a writing stand point they never quite hit it right on. To make the character likable they have always gone with "I don't want to do it but I don't know anything else" or "It's part of my life, I can't escape it" and sometimes even ripping off gangster movies (Case in point GTA:SA which is remarkably like Boyz n the hood) for the characterization.
I would say it's as easy as picking the characters motivations to start- even bad guys think they're doing something that is right and you can find something in that that anyone can relate to, but putting it on paper is really hard to do and make it cohesive. Even more so to put it to interactive storytelling makes it a pretty difficult task.
I think that's why they changed direction lately... maybe. When they do anti-hero's (RDR) and full on good guys (LA Noire) the writing seems much better and makes more sense. To me anyway. I know the development teams are different, but rockstar had their hand at least a little in each so my point still stands.
Just my thoughts on it. I haven't played GTA 4 but I played all of them up to it and I have felt that way for awhile. GTA 4 was just the one where it seemed to be most obvious to everyone all of a sudden since it wasn't novel anymore I guess.
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