- Slick Rick
- Big Daddy Kane
- LL Cool J
- Ice Cube
Most Helpful Guy
It really comes down to what you like. I love rap, this is what I grew up on, so this is such a hard question for me, as experienced as I am with it.
Of those listed, I'd probably go with Rakim, because he was the bridge from old school rap to a newer brand and newer flow. He got deep in his lyrics, and got away from the choppy and somewhat awkward cadence of what HS preceded him, like Run DMC, for example. So he kind of changed the game, not that old school isn't dope in its own right, but it opened the door to the Golden Era.
I love Cube, I was really into West Coast gangsta rap and G funk and all that, and if you put a gun to my head and made me pick an all-time favorite song, I'd probably say "It Was A Good Day." He's a personal favorite, but for whatever reason I don't always think of him in that top, TOP echelon if I'm being technical. I actually like him a lot as an actor, minus Are We There Yet, haha. Doughboy in Boyz N The Hood was a great character, and I think his role as Fudge in Higher Learning is as underrated a performance as I can think of.
Kane, Cool J, and Slick Rick are all legends, but still, like Cube, I don't quite put them there. KRS, I actually opened for once at a local venue, I used to just fuck around a little and rap with some friends, we had a small following, it's was no big deal, but we got the call and WOW, what an experience. Nothing makes you feel more amateur than being followed by KRS-One, hahaha. But I liked all that BDP stuff, and he deserves to be in the conversation.
Pac and Biggie as you said, it's been done to death. Both great. Nuf said.
Staying on the theme of dead rappers, Big L never got off the ground, same with Big Pun, and this is just a quick honorable mention.
Where's Nas at? He's a tough call because he kind of peaked early. But Illmatic is a cover to cover classic, and not in a commercially popular kind of way, but just a hurricane of perfection. Lyrics, beats, flows, hooks... good god. I liked 80% of It Was Written too, and I Am and Stillmatic were aiiiight, but when it was hot it was hot.
I could go on all day, but I gotta go for now, so I'll leave it with no decisive answer, hahaha.