Source: VALERIE MACON / Getty The Rappers With the Most Grammy Wins in Hip-Hop History The GRAMMY Awards have become one of the biggest markers of success in music, and hip-hop artists have been stacking trophies for decades. Here’s a breakdown of the rappers with the most Grammy wins of all time and why each one changed the culture. His Grammy wins span production, rap, and crossover categories — proof of how far his vision pushed the genre forward. Even with a short solo catalog, her impact remains massive — and her Grammy wins solidified her place in history. As a producer, mentor, and artist, Dre’s influence reaches every corner of the genre — making his Grammy wins just one part of a massive legacy.