I am listing to my "purchased" playlist on itunes, in the order in which I purchased the music. It is 3283 items, spanning 11.5 days. It will take me more than that to listen to it, since I can't listen 24 hours a day. It starts out with Coleman Hawkins "Body and Soul," then skips to Feldman's "Rothko Chapel." Unfortunately it cannot ever get better than that, but it has more Morton Feldman after that, then Mozart's quartets dedicated to Haydn, some Sonny Rollins and Stan Getz and Lee Konitz. Keith Jarrett. Sinatra's wee small hours. A Tsaik symphony. Joe Pass's "Virtuoso." I'm not sure when this was, since I don't know how to figure out the exact chronology. I do know I was listening to Joe Pass while writing 1st Lorca book, which is about 2006.
Coming up is some Bach and Shakespeare.
My brother-in-law Norbie Kumagai gave me an airport express he wasn't using, so I can stream the music from my laptop to my stereo speakers. I have other music that's not purchased (downloaded from cds in instead). That would be my other 5000 songs that I'm not worried about right now.
You could do something similar if you kept track of all the books you've bought or checked out of the library.