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I’ve found making playlists based on music releases from each year helps with this… for me I can almost immediately remember a year or time period just by hearing a song
Quite a few tracks - does one say that anymore? - I am convinced are 1980s are actually 1990s. I’m Gen X so I should be getting that distinction right!
You can just use the songs you listened to most in a given year too. Assuming you’re mainly listening to old music, my original suggestion probably won’t work.