So I'm sure you're familiar with ipod shuffling quizzes, where you answer questions like:
How are you doing today?
Last night was:
Will you get married?
With answers from your selected media player, which has been tactfully shuffled by the fates and dealt out, sometimes with surprisingly accurate results and sometimes with odd songs that don't make sense with the question.
So what you do here is essentially that, except you formulate questions (a variable number of questions, however many you want) for the next person, who in turn answers these questions with songs from their musical horde and asks their own questions for the next person, who etc.
So hop to it!
(Just answer the questions I put as the examples, then go from there)
