A good compilation tape, like breaking up, is hard to do and takes ages longer than it might seem. You gotta kick off with a killer, to hold the attention. Then you have to take it up a notch, but not blow your wad, so maybe cool it off a notch, and you can't put the same artist twice on the tape, except if some subtle point or lesson or theme involved, and even then not the two of them in a row, and you can't woo somebody with Joni Mitchell's "Big Yellow Taxi" and then bash their head off with something like GBH's "City Baby Attacked by Rats," and... oh, there are a lot of rules.
High Fidelity, Nick Hornby.