The Longest Mixtape
https://www.youtube.com/playlist?list=PL4lEESSgxM_5O81EvKCmBIm_JT5Q7JeaI Caribou, aka Dan Snaith, has put together "The Longest Mixtape," a collection of 1000 songs important to him. You can check it out below. (Because of YouTube's coding, only 200 of the tracks are cycled in the embed—you'll have to click through for the full 1000.) It includes tracks from Kanye West, Arthur Russell, Madvillain, the Zombies, Pusha T, Wire, Missy Elliott... and too many others to list.
Listen to them in order, because there is no order.