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.
Christopher Mario Testa
In 2007 the Dixie Chicks won 5 Grammy's at the 49th Grammy Awards. The record won every coveted award including Album of the Year, Record of the Year, Song of the Year, Country Album of the Year, and Best Country Performance by a Duo or Group with Vocal. This marked the first time any band has won that many Grammy awards in the same year. Chris won Grammy's for 3 of the 5 including Album of the Year and Record of the Year. The record went on to sell almost 4 million copies worldwide and was #1 on Billboards Top 200 albums for 2 weeks in a row reaching gold status in the first week.