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 Amy Winehouse
The Grammy Awards are awarded annually by the National Academy of Recording Arts and Sciences of the United States for outstanding achievements in the record industry. Often considered the highest music honor, the awards were established in 1958. Winehouse received six awards from eight nominations, the last of which was
received posthumously.
Note: The documentary film "Amy" (2015), won Best Music Film at the 2016 Grammy Awards. This award is credited to the director Asif Kapadia and the producer James Gay-Rees.