We've always said albums not single tracks and it was five same as Raza (and greatest hits don't count). My tops are pretty easy but rounding out the five sometimes proves difficult. Anyway, here is my attempt at 5:

1. "Closing Time" - Tom Waits
2. "The Earth Sings Mi Fa Mi" - The Receiving End Of Sirens"
3. "Zeppelin (I or IV, can't decide)" - Led Zeppelin
4. "In Keeping Secrets of Silent Earth: 3" - Coheed & Cambria
5. An album that has Rachmaninoff's piano concerto 2 (and preferably something else too), performed by Rachmaninoff or Arthur Rubinstein

For a book, either Atlas Shrugged or The Fountainhead