Marley Marl comes to mind as someone who has had contact and work with a wide swath of MCs, so I feel like he'd be interesting - possibly. I haven't ever heard an interview with him, so I'm not super sure what he's like personality-wise. I doubt he's as dynamic as Paul, but on paper it seems like he should have enough stories for multiple episodes.

The Beatnuts to me have a lot of production credits to their name in addition to their own work - all over the place in terms of connections. PLUS they seems like they have a strong sense of humor and would be fun to listen to.

Madlib could surely sustain an entire season, but obviously a different era. Beyond that, I would be interested in a lot of those semi-underground dudes from the West Coast, thinking about all the Hieros, Freestyle Fellowships, etc - if one could identify a central figure from that world.