Sharing some of the diversity of hip-hop with my son

My son recently commented that all hip-hop sounded similar, and I realized immediately that I was failing him in his music education! Basically he's listening to a limited selection from mainstream sources. I enjoy a variety of hip-hop old & new, but my hip-hop education also limited. I thought I'd ask r/hiphopheads if anyone was willing to share their advice:

What songs would you recommend to give someone a quick overview of the diversity of hip-hop over time? (I think larger genre's though, not really obscure/experimental stuff. I'll ask you guys about that in a follow-up post!) What's songs should everyone know?

Really appreciate your help and I'm excited to expand my and my son's horizons!

submitted by /u/spctraveler
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