Back in May I started listening to every CD I own, in the order that I bought them, starting with Eugen Jochum conducting Mozart's Mass in C-Major, K317 (purchased in May 1988). I'm up to July 1989 now, and as I write this, I'm playing The Mama's and the Papa's [sic] If You Can Believe Your Eyes and Ears (1967). This follows The Beatles' With The Beatles (1963) and Paul McCartney's Pipes of Peace (1983).
And then it goes sideways.
Next up: Haydn's Piano Concerto #11 (1781), and Josquin's "Missa L'Homme Armé" (ca. 1500). I bought those five CDs on 7 July 1989.
Three days later I acquired a batch of six, including a collection of English madrigals sung by the King's Singers, Oscar Levant playing Gershwin, and the soundtrack from The Breakfast Club.
There are stretches of classical and stretches of modern throughout this list, but right now I'm in summer break after my first year of college when I was expanding both sides of my collection as fast as I could afford to.
I just did some math: at the rate I'm going, I'll be out of my university years around November 17th, in the 21st Century around the beginning of April, and through all of them in the fall of 2021. (That's a moving target for obvious reasons.)
It's a little trippy. I haven't heard some of these in a long, long time.