Jay-Z (24 Grammys)
Shawn Carter, known widely as Jay-Z, won his first Grammy for Best Rap Album in 1999 with his Vol.2: Hard Knock Life. His most wins in a single night were in 2010, 2011, and 2013, where he won three awards each. The 53-year-old rapper has 88 Grammy nominations, tying with his wife Beyoncé for the most individual nominations in Grammy history. Jay-Z tied with Kanye West as the rappers with the most Grammys (24 each).
