As I said, roleplaying is very easy in Oblivion and other like single-player games, as long as you can project and transform your own thinking into thinking like your character. To me, it's no more difficult than roleplaying in MMORPGs, with the added benefit of never having to come upon gold scammers, RP griefers, atrocious leet speak, or anything else that hinders you from staying in character.

Oblivion begins with your character in prison, and an event sets in motion your escape and gives you a quest, which you may or may not undertake. I've created four solid characters who have all gone through that event, and immediately after finding freedom, I stop and think, why were they in prison in the first place? Once I have that in mind, I then ask myself, what if any bearing does that fact have on what I will do next? Those two questions have been more than enough for me to create a distinct and different personality for each, thereby allowing me to play through the very same game, yet experience it in four unique ways. Remember, Oblivion is a two-year-old game, yet not once has it ever been old or boring for me. Safe to say I've gotten my money's worth.