Find what you like and then deep dive into that genre. Learn the history about it, look up the producers, the stories behind the albums, the songwriters, the studios that they were recorded at even.

A lot of historical context can be built from that. And you also find more artists that way. Also if you really want to get into it, look up the instruments that are influential in the process of the albums you find. For example, J Dilla's MPC was one of the most important tools of the 90s Neo-Soul and Hip Hop scene (it's actually in the Smithsonian). But other producers have mastered it and its decedents... like Araab Musik, Pete Rock, or Kanye.

If you want to be a person who respects all different genres of music, look into the history of genres as you explore them and find the most influential albums in that genre (usually this correlates to albums sells for "popular" music, influential is usually tied to the network of artists someone has influenced, worked with, produced for, etc).

Hopefully that helps. I'm a huge music buff, so I'd be happy to discuss.