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. 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!