only a one sided person would think a gangster wouldn't listen to music like that. You have a very cliched image of a gangster in your head "Rappers" Rappers aren't gangsters. Rappers take what gangsters do and put it to rhymne. Just cause its about gangsters, doesn't mean gangters listen to it.
The gangsters in Reservoir Dogs (if you can even call them gangsters, considering they are bank robbers) are also not very young. They are in their thirtees and fourtees and fifties. Rap wasn't around during their time. They didn't listen to that type of music.
Plus its personal preference. Just cause I live in an age of rap and hip hop, doesn't mean I listen to it. I prefer older stuff cause its SOUNDS better. And I think Madonna's old stuff is pretty good.
Now as for a gangster not listening to that. Do you know many gangsters? I think gangsters would listen to whatever sounds good, not what fits the situation "Oh, I'm bout to rob a bank, I gotta listen to music bout robbing banks" They listen to whats on the radio and whats right.
Get cliches stuck outta your head Stuck in the Middle. Gangsters dont' always listen to "cool" music. Tarantino made realistic characters here, he avoided most cliches.