Rappers With the Most Grammys: Jay-Z, Kanye, Kendrick and the Rap Win Leaderboard
Rappers with the most Grammys: Jay-Z 25 wins as of 2025, Kanye West 24, Kendrick Lamar 22 plus 2026 ROTY canon, Eminem 15, Missy Elliott, Lauryn Hill, Drake snub narrative, 1989 boycott.