[mushufasa]

There's the beatles, which are worth following chronologically as a sense of how pop music evolved. The "Beatles Anthology" documentary series is great.

Other than that, music is really too diverse and varied to approach systematically IMO, especially from the perspective of individual taste (as opposed to, say, academic ethnomusicology). My suggestion would be tasting assortments of artists within subgenres until you stumble upon something you love, and branching from there. The free NTS internet radio station (https://nts.live) has a lot of searchable shows curated by musicians, so I really recommend that resource for exploration.