This is a tough one, but in no particular order...well maybe sorta
1. Slick Rick - His charisma is unparalleled and the greatest storyteller Hip-Hop has ever had
2. Big Daddy Kane - The prototype! He was the guy every dude wanted to be and the guy every girl wanted to be with. Unmatched versatility
3. Grand Puba - A fashion icon beyond his time. He truly embodies swagger
4. Jay-Z - Quite possibly the greatest contributor to current Hip-Hop. He is truly the ambassador, plus he mastered & redefined the conversational flow.
5. Black Thought - Rhythmically the best. Very few can control their flow as well as he does, and he does one hell of an impersonation of my favorites.
5. Nas - when he is on, he is brilliant
6. Common - Some may argue that # 5 holds the title, but I'd argue that Comm is the greatest pure poet in Hip-Hop. His transition from thought to thought is out of this world!!
7. 2Pac - no one showed as much vulnerability and touched our hearts in the way he could. He gets the award for most conviction & passion.
8. B.I.G - In 1 word; charming. In 2 words; captivating. He also laid the blueprint for commercial success
9. Ghostface - A great storyteller and the king of incoherent thoughts. Easily one of the most entertaining to just listen to.
10. Ludacris - before you get your panties in a bunch, dude is deceptively ILL. He can literally out-rhyme the best, but you would never know based on how popular he is, and how big his songs are. In 1 word; underrated!!!
It should also be noted that this list is based on "MY" current taste and is relative to time. I obviously have favorites like Eminem, Pun, Redman, & Andre that I didn't include. These are my favorites as of today. The true school crowd are so influential, they'll always be a staple but the others could change in a few months. Anyway...DEBATE!!!!!