18. Derek Jeter
Namedrop: “Ringleader set it off, rap Derek Jeter, Culprit, prince of the game wish you could see us” – Ghostface Killah, “Mighty Healthy,” Supreme Clientele
If Jay-Z could swing a baseball bat, he would be Derek Jeter. Defined by his unshakable cool and as quite possibly the greatest Yankee of all-time, “The Captain” might be the only person in New York who lives just as good as the God MC. From his legendary laundry list of dames he’s allegedly chopped down to his endless list of accolades as a shortstop for the real “America’s Team,” it’s easy to see why Hip-Hop has and always will have love for DJ.