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.
Pinetop Perkins
At the age of 97, Perkins won a Grammy Award in the category Best Traditional Blues Album for "Joined at the Hip", which he recorded with Willie "Big Eyes" Smith, thus becoming the oldest winner of a Grammy Award, edging out the comedian George Burns, who had won in the spoken word category 21 years earlier.