Digable Planets - Rebirth of Slick (Cool Like Dat)
This track is one of those immediate classics. The rest of the album, Reachin' (A New Refutation of Time and Space,) is good but this is the distinct stand out. This came out around the time A Tribe Called Quest was popular and a lot of New York rap was exploring Jazz roots. This song outdoes them all in my opinion.
Common - Sixth Sense
This is off one of Common's earlier albums, Like Water For Chocolate. This Chicago MC is one of my absolute favorites. He's got an incredible flow, wordy vocabulary and a great voice. I love most of Common's works, he's got a huge soul influence that adds that extra funk in his music. DJ Premier, from GangStarr, did the beat for this song, one of my favorites Premier has ever done.
Notorious B.I.G. - Juicy
It was all a dream! Sing these first few lyrics to any true hip hop fan and you'll both be beatboxing and rapping the lyrics to this hip hop gem for a while. This song is an absolute classic that catapulted Biggie into new heights. The beat is smooth and funky, Biggie's lyrics of rising above can relate to anybody. How can you not like a song with lyrics including "thinkin' back on my one room shack now my mom pimps a hat with minks on the back."
Nas - The World Is Yours
The whole album, Illmatic, is incredible but this is the standout gem to me. This was Nas' debut album and hit the hip hop world like a ton of bricks. His later work tends to get a little more stale as time progresses from this album. His second album It Was Written was good too, but it doesn't have the breath of fresh air that Illmatic is.