Back in May, which seems like ten years ago rather than ten months, I started going through all my CDs in the order that I acquired them. I don't listen every day, and some (like Bizet's Carmen) take a bit more time than others (like a 4-song mini CD of Buddy Holly songs).
I've now arrived at about the middle of my collection, with a set of four CDs I bought on 19 September 1993. Holy Alternative, Batman. I had just started doing one shift a week at WLUW-Chicago, Loyola University's radio station, having made a deal to take the unpopular Saturday 8pm to midnight shift in exchange for doing whatever I wanted. They agreed, and I started the only Alternative show on what was then an all-dance station.
So the next four I've got cued up: the Charlatans UK Some Friendly, Eno & Cale Wrong Way Up, the Cure Disintegration, and U2 Zooropa.
These really take me back. Not that I'd experience my 20s again without knowing what I know now (or, at least, without the emotional maturity I've earned since then), but I did like the music.