9. Ken Rosenberg (GTA: Vice City & San Andreas)
Ken Rosenberg is a rather unsubtle homage to Sean Penn's character Dave Kleinfeld in the movie Carlito's Way, meaning that he's a highly immoral, cocaine-addicted, back-stabbing lawyer, and also one of the best characters in the entire GTA franchise. His coke habit ensures that he's a motormouth during most of his interactions with Tommy throughout the game, but his sheer ballsiness to stand up to both the law and other gangsters is admirable, especially given his otherwise quite nerdy look. Though he might not seem stable, Ken proves to be one of the few mainstays during Tommy's adventure, and someone he can always come to for help. Rosenberg resurfaces in San Andreas, though soon enough picks up his cocaine addiction once again, and is basically a mere shadow of his former self. Oh, and he's voiced by William Fichtner; how about that?