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.
List of awards and nominations received by Frank Sinatra
Nominated – Academy Award for Best Original SongThe Grammy Awards began in 1958, after two peaks of Sinatra's recording career had already happened, but Sinatra still won eleven Grammy Awards – his work was nominated over 30 times – in his career and has been presented with the Grammy Hall of Fame Award along with the Academy's highest honours, their Lifetime, and Legend Awards. With three wins he is one of only five artists and groups who have won the Grammy Award for Album of the Year more than once as the main credited artist.