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.
Al Schmitt
He has won more Grammy Awards, more than any other engineer or mixer. He was the first person to win both the Grammy and Latin Grammy for Album of the Year. He won his first Grammy in 1963 for engineering the "Hatari!" soundtrack by Henry Mancini. The song "Moon River" and its won two Grammy awards in 1961 as well as an Academy Award for Best Song with its appearance in the film "Breakfast at Tiffany's". He was awarded two Latin Grammy Awards in 2000 including Album of the Year. In 2005 he won five Grammys for his work on Ray Charles' "Genius Loves Company", including Album of the Year, setting the record for most Grammys won by an engineer or mixer in one night. In 2006, he was given the Grammy Trustees Lifetime Achievement Award.