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I am an entitled white male; I've played (and beaten) all the GTA's since 3, except "Liberty City Stories". I didn't find SA discomforting at all.
To me, the implied subtext is that his situation is uncomfortable, because either he or his friend is a racist. Maybe I'm wrong. I don't play many games, but I do love the GTA series - for me it's mostly about the driving and the flying, and to a lesser extent, the combat. Love the humour throughout.