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.
List of awards and nominations received by Justin Timberlake
The Grammy Awards are awarded annually by The Recording Academy of the United States for outstanding achievements in the music industry. Considered the highest music honor, the awards were established in 1958. Justin Timberlake has won 10 awards out of 39 nominations. His wins include categories on the pop, dance and R&B fields. 8 nominations as part of NSYNC are counted. Two of Timberlake's studio albums have been nominated for Album of the Year so far: "Justified" in 2004, and "FutureSex/LoveSounds" in 2007.