Allright, I never joined in this thread because I have TOO Much music.
I let winamp scan my archive now and I will now try to add all my tracks (26433), 74 days of music) to a playlist to see what happens...
This could take a while...
Oh, that went surprisingly fast

I should ask that I have quite some discographies so in some cases I haven't heard every song that's in the list

*Randomize*
1. Jethro Tull - We Five Kings
2. The Doors - When the Music is Over
3. Susan Cadogan - Nice and Easy (by Lee Perry)
4. Jethro Tull - Sossity you're a Woman
5. Lee Perry - Inspector Gadget 2004
6. King Tubby - Dubbing my Way
7. Bob Dylan - 10.000 men
8. Beirut - A Sunday Smile
9. zZz - Majeur
10. Fleetwood Mac - Angel
Haha, I can't believe how ****ed up it randomised.
I actually know just two of these songs

.
I have heard some of them before, but I never really went and played any of these songs or albums they come from. That's incredible.
Ah well, here you go.
As I have never done this before, I'll give it another go rightaway.
I scrolled down and now will go from 31 to 40:
1. Django Reinhardt - Viper's Dream
2. John Scofield - Beckon Call
3. Babylon Circus - Lorenzo
4. The Levellers - I have no answers
5. Paolo Conte - Le Scapolo
6. Trampled by Turtles - Seperate
7. The Grateful Dead - Walkin' Blues
8. Tim Armstrong - Lady Demeter
9. The Bees - Sweet like a Champion
10. Jethro Tull - Velvet Green
That's better. I know 7 of those tracks

.