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.
Bobby McFerrin
McFerrin has won ten Grammy Awards, ranging from the 28th ceremony for releases from 1985, and the 35th ceremony for releases from 1993, and has won a record total of four awards for Best Jazz Vocal Performance, Male, surpassing Harry Connick Jr., who has since won this accolade twice.