open up a new smart playlist in iTunes (it's what i use), and enter
Name > Contains > ?
(you could try 'who', 'what', 'when', 'where', or 'why' in place of '?' if it's not yielding enough results)
then shuffle the list and use the first 15 song titles as your questions. write them down. then, finally, shuffle through your whole library to answer your questions (you did write them down didn't you?) Oh, and no cheating to make your answers better... sinner.
Q: What is Fight Club?
A: Like Toy Soldiers
fight club is like toy soldiers? umm, i don't get it.
Q: What About Me?
A: Twist & Bend
apparently i like to twist and bend... it's much quieter than twist and shout, but sadly not as much fun.