Alison Krauss
As of 2018, she has won 27 Grammy Awards from 42 nominations, tying her for the second most awarded recipient alongside Quincy Jones, second only to classical conductor Georg Solti, who holds the record for most wins with 31. She is the most awarded singer and the most awarded female artist in Grammy history.
Grammy Award for Best Rap Song
Kanye West holds the records for the most wins and nominations in this category, having won six times out of nine nominations. He is followed by Jay-Z with three wins and six nominations. Following the two, Kendrick Lamar has three wins, and Pharrell has two wins. No further songwriters have won this category more than once. T.I. (a.k.a. Clifford Harris) holds the record for most nominations without a win with four.