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.
Stevie Wonder
A prominent figure in popular music during the latter half of the 20th century, Wonder has recorded more than 30 U.S. top ten hits and won 25 Grammy Awards (the most ever won by a solo artist) as well as a Lifetime Achievement Award. He has also won an Academy Award for Best Song, and been inducted into both the Rock and Roll and Songwriters halls of fame. He has also been awarded the Polar Music Prize. American music magazine "Rolling Stone" named him the ninth greatest singer of all time. In June 2009 he became the fourth artist to receive the Montreal Jazz Festival Spirit Award.