Mostly replying as a personal challenge; I doubt anyone cares about my opinion. I think this is a hard but interesting challenge and I could probably spend a lifetime perfecting it, but this is my unadulterated first pass:

“Stardust” - Willie Nelson

“Melancholy and the Infinite Sadness” - Smashing Pumpkins

“Blue Lines” - Massive Attack

“Kind of Blue” - Miles Davis

“Wildflowers” - Tom Petty

“Blind Melon” - Blind Melon

“Loaded” - The Velvet Underground

“At War with the Mystics” - The Flaming Lips

“Dire Straits” - Dire Straits

“Pretty Hate Machine” - Nine Inch Nails

Fuck. How do you make a list like this without regretting every decision you made?!