Two very good questions, Bri and well worth pondering. A third could be, "Drinks on a Monday night?"

As to the first ?, how about:

"Slanted and Enchanted" - Pavement
"Funeral" - Arcade Fire
"The Stone Roses" - The Stone Roses
"The Smiths" - The Smiths
"Is This It?" - The Strokes
"The Velvet Underground and Nico (banana) - Velvet Underground
"Unknown Pleasures" - Joy Division
"Surfer Rosa/Come On, Pilgrim" - The Pixies
"Murmur" - R.E.M.
"Debut" - Bjork