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Most wins in one night: In 2011, Frost won four awards, including best classical album and best choral performance, both for Verdi: Requiem. The best-selling female Gospel singer of all time, Winans - already the genre's most decorated GRAMMY-winning singer - entered the show's 64th annual ceremony Sunday ( April 3) up for three. Leah Peasall of The Peasall Sisters is the youngest ever Grammy nominee (and winner) as one of the credited artists on the O Brother, Where Art Thou? Her albums have sold over 17 million albums in the US and over 100 million worldwide. Notes: Gill, 65, has won more Grammys than any other male country artist. In 2006, they released Taking the Long Way, which took top Grammy album honors for both Album of the Year and Best Country Album. From nine nominations, she accepted awards for Best Dance/Electronic Album (Renaissance), Best Dance/Electronic Recording (Break My Soul), Best R&B Song (Cuff It) and Best Traditional R&B Performance (Plastic off the Sofa), increasing her tally since 2001 to 32 one more award than conductor/musical director Sir Georg Solti won between 1963 and 1998, and extending her lead among female artists, with bluegrass vocalist/fiddle player Alison Krauss having won 27 awards in 19912012. Shes been credited with helping renew the interest in bluegrass in the US; and at the time of her first Grammy win in 1991, she was the second-youngest winner. Her most recent win came in 2018 from her song "Loyalty," which featured Kendrick Lamar. Most Grammy Award-nominated individuals of all time | Statista Two engineer/mixers and one mastering engineer have won the award four times; Four recording artists, four record producers, two engineer/mixers and two mastering engineers have won the award three times; The record for most Record of the Year wins is four. Of the 14 artists with the most awards in Grammys history, only two of those are women. Most wins in one night: He won three awards in 2010, 2011 and 2013. Beyonce - 32 Grammy Awards As of the 2023 Grammy Awards, Queen Bey is the equal most-awarded person in the ceremony's history, with 32 awards. They are one of just three groups or duos to win record of the year twice. Beyonc smashes Grammys record for most-winning female singer - USA Today In 1981, Christopher Cross became the first artist to win all four awards, as well as the first act to win them all in a single year. Women havent always been so readily acknowledged by the Recording Academy, however.