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.
James Fauntleroy
The Grammy Awards are awarded annually by the National Academy of Recording Arts and Sciences of the United States for outstanding achievements in the music industry. Considered the highest music honor, the awards were established in 1958. James Fauntleroy has won 4 awards out of 5 nominations.