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.
Don Henley
The Eagles have sold over 150 million albums worldwide, won six Grammy Awards, had five No. 1 singles, 17 Top 40 singles, and six No. 1 albums. They were inducted into the Rock and Roll Hall of Fame in 1998 and are the biggest selling American band in history. As a solo artist, Henley has sold over 10 million albums worldwide, had eight Top 40 singles, won two Grammy Awards and five MTV Video Music Awards. Combined with the Eagles and as a solo artist, Henley has released 25 Top 40 singles on the "Billboard" Hot 100. He has also released seven studio albums with the Eagles and five as a solo artist. In 2008, he was ranked as the 87th greatest singer of all time by the "Rolling Stone" magazine.