I guess I would prefer to choose one album over any eight songs, but let's stick to the given format. For obvious reasons, longer songs get the edge with me. I'd also prefer abstract songs, because they don't tire as easily.
1. Neu! - Hallogallo
2. Boards of Canada - Happy Cycling
3. Nina Simone - Sinner Man
4. Tom Waits - Tom Traubert's Blues
5. Massive Attack - Angel
6. Autechre - Cipater
7. Radiohead - Paranoid Android
8. William Basinski - D|P 1.1 (at 63"00')
Book: Cormac McCarthy's 'The Road' or William Faulkner's 'As I Lay Dying'. Hard choice. I'd choose the first, because it would fit better to the situation. Possibly.
Luxury item: Assuming I do have a way to play my beloved songs, a computer with internet connection. Is that allowed?
Great pick with Hallogallo and I like the cheekiness of putting in The Disintegration Tapes hehe. And a quick search for the luxury items show that the celebrities pick items from a trowel, a laptop, unlimited paper, an Aston Martin DB9, pillows, pianos and unlimited mojitos. I know which of those I'd prefer :)