| 100% | JONIMITCHELL | 12 | Singer-songwriter who sang "Both Sides Now" at the 2024 Grammy Awards in her first-ever Grammy performance (2 wds.) |
| 66% | TRACYCHAPMAN | 12 | Singer-songwriter who sang "Fast Car" at the 2024 Grammy Awards in a rare public performance (2 wds.) |
| 53% | MILEY | 5 | With 32-Across, singer-songwriter who exclaimed "I just won my first Grammy!" during her performance of "Flowers" at the 2024 Grammy Awards |
| 48% | LAINEYWILSON | 12 | "Bell Bottom Country" singer who won Best Country Album at the 2024 Grammy Awards (2 wds.) |
| 46% | VICTORIAMONET | 13 | "Jaguar II" singer who won Best R&B album and Best New Artist at the 2024 Grammy Awards (2 wds.) |
| 46% | ARETHAFRANKLIN | 14 | "Queen of Soul" who sang the National Anthem at the 2006 Super Bowl in her hometown of Detroit: 2 wds. |
| 45% | LAURIEANDERSON | 14 | "O Superman" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 45% | BILLIEEILISH | 12 | "What Was I Made For?" singer/co-songwriter who won Song of the Year at the 2024 Grammy Awards (2 wds.) |
| 45% | JONIMITCHELL | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2001 Vocal Jazz Album of the Year Juno Award for "Both Sides Now" (2 wds.) |
| 45% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 45% | TAMMYWYNETTE | 12 | "Stand by Your Man" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 45% | GLADYSKNIGHT | 12 | Leader of the Pips who sang the National Anthem at the 2019 Super Bowl in her hometown of Atlanta: 2 wds. |
| 45% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 44% | JORDINSPARKS | 12 | Season 6 "American Idol" winner who sang the National Anthem at the 2008 Super Bowl in her hometown of Phoenix: 2 wds. |
| 44% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 44% | WILLIENELSON | 12 | "Always on My Mind" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 44% | TAYLORSWIFT | 11 | Multiple Grammy-winning singer-songwriter who is the first-ever recipient of Billboard's Woman of the Decade Award: 2 wds. |
| 44% | IGGYAZALEA | 10 | "Fancy" singer featured on "Problem" who in 2014 became the second ever to be simultaneously #1 and #2 with her first two hits: 2 wds. |
| 44% | JONIMITCHELL | 12 | "Both Sides Now" singer who was MusiCares Person of the Year in 2022: 2 wds. |
| 43% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 41% | SARABAREILLES | 13 | "Love Song" singer/pianist who performed a duet with 18-Across at the Grammy Awards in 2014 (2 wds.) |
| 41% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 41% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 40% | ADELEADKINS | 11 | British singer whose third studio album fetched her the Album of the Year in the 2017 Grammy Awards : 2 wds. |
| 40% | ETHELWATERS | 11 | Harlem Renaissance singer and actress who was the first African American to star in her own TV show: 2 wds. |
| 40% | RENEEFLEMING | 12 | Opera singer who sang the national anthem at the Super Bowl in 2014 and received the National Medal of Arts in 2012: 2 wds. |
| 40% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was honored with the 1972 Grammy Award for Best Male Country Vocal Performance (2 wds.) |
| 40% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 40% | KYLIEMINOGUE | 12 | "Padam Padam" singer who received the Billboard Women in Music Icon Award in 2024: 2 wds. |
| 39% | ALICIAKEYS | 10 | "Songs in A Minor" singer/songwriter who won the 2021 Audie Award for Narration by the Author for her memoir "More Myself" (2 wds.) |