Jay Z
This Brooklynite set new rules for the industry and winning Grammys is one of them. It’s no question that this rapper has survived the test of time in the rap game for so long and put these new rappers to shame. He won his first Grammy back in 1999 for Best Rap Album, for Hard Knock Life Volume Two but refused to go to the ceremony because they didn’t televise the category. Since winning his first Grammy, he became the first rapper to win many countless Grammys alongside singer Beyonce who eventually became his wife.
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