If you’re looking for a comprehensive guide to pop music, from the 1950s to around 2010, Bob Stanley’s “Yeah Yeah Yeah” is it [affiliate link]. It’s roughly chronological and covers everything from the introduction of vinyl (the “official” start of pop music) to downloads (the end).
Every page leaves you with a list of songs you want to listen to. The volume is such that you’ll never get around to finding all of them but I did end up listening to a bunch of stuff that I wouldn’t ordinarily have thought to. Ironically, by being published in 2014 it misses the mainstreaming of the very streaming services that allowed me to do that!