These days it's all about personalised, targeted rolling. You have to find out what song your friend hates the most (say, "Africa" by Toto) and try to trick them into listening to ever-more-horrible cover versions of it.
At least, that seems to be the thing in my friend group.
I don't know if that really works though. It's a bit like gift giving: the point is arguably more to show off the effort you personally put in just to prank your friend.