As silly as it sounds, I have a hard time enjoying mob movies for similar reasons. How am I supposed to feel bad when someone who steals, threatens and kills for a living gets robbed, threatened and killed?
Sometimes I think people feel like they're sticking it to the man, the same man that is holding them down and preventing them from being successful.
But a fascinating experiment is giving a game like Animal Crossing to a non-gamer. My mother and a friend of mine, upon being dropped into my Animal Crossing city, both did the same thing: run around and trample flowers. It is the easiest thing to do that has an immediate effect on the world, with a visual component to it. Since it doesn't hurt anything "real" they don't have any connection to it or understanding of it, it's like they're reliving their childhood.
Fast forward a month or so and my mother has gone out and bought her own Gamecube, has multiple cities and characters with themes/personalities for all of them.
It's very interesting to see that process, that progress from a child that knows only shiny colors and loud noises to an adult that appreciates and influences their place in the greater scheme of things.