Well, let's start with the 8 songs:
Sweet Child O' Mine - Guns N' Roses
Without a doubt my favorite songs of all time.
Walk This Way - Aerosmith
This song kicks major ass and has some swag.
Stairway to Heaven - Led Zeppelin
I was tempted to make all eight songs come from my favorite album, Led Zeppelin IV, but I decided to go with just this song (which I love).
All Along the Watchtower - Jimi Hendrix
Best cover ever, yada yada yada.
Strawberry Fields Forever - The Beatles
My favorite Beatles' song.
Bohemian Rhapsody - Queen
Probably my favorite songs from my favorite group.
(Sitin' On) The Dock of the Bay - Otis Redding
A great slab of soul.
(I Can't Get No) Satisfaction - The Rolling Stones
The last song was the hardest to pick, because it's the last one.

Now for the book:
1984 - George Orwell
That book is the shit.

As for the luxury item, I'm having a hard time chosing between a guitar (which I would enjoy playing) and an oven (so I could eat). Interesting choice.

This is next to impossible. There's no collection of eight songs I'd never get tired of. But away we go anyway.

The Cure - The Same Deep Water as You
Stevie Wonder - Another Star
Jeff Buckley - Forget Her
Reigning Sound - Let Yourself Go
R.E.M. - Laughing
The Smiths - Heaven Knows I'm Miserable Now
Teenage Fanclub - Your Love is the Place Where I Come From
Steely Dan - Don't Take Me Alive

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 :)