9. Jim Jones & Juelz Santana

Heritage: Jim: Puerto Rican; Juelz: Dominican
Hustle: Rappers

At their peak, the Diplomats basically had leeway to tell anyone on the planet, “You mad ‘cuz I’m stylin’ on you.” Cam’ron made the hood love pink, but scratch beneath the flamboyance and you’ll notice that Juelz and Jimmy were no slouches. You can almost single-handedly blame the two for getting dudes to slim down on the mountains of fabric they were used to wearing. These two were on their pretty boy shit, for sure, but we got concerned when Jimmy chopped his braids and went for the S-Curl world cup look.