| 100% | GLADYSKNIGHT | 12 | Grammy-winning singer honored by the 50-Across with a Lifetime Artistic Achievement Award in 2022 (2 wds.) |
| 86% | GEORGECLOONEY | 13 | Oscar-winning actor honored by the 50-Across with a Lifetime Artistic Achievement Award in 2022 (2 wds.) |
| 69% | DEBBIEALLEN | 11 | Dancer/choreographer/actress honored by the 32-Across with a Lifetime Artistic Achievement Award in 2021 (2 wds.) |
| 69% | GARTHBROOKS | 11 | Country music star honored by the 32-Across with a Lifetime Artistic Achievement Award in 2021 (2 wds.) |
| 51% | NINASIMONE | 10 | Blues singer honored with a Grammy Lifetime Achievement Award (2 wds.) |
| 51% | SHIRLEYCAESAR | 13 | Gospel singer honored with a Grammy Lifetime Achievement Award (2 wds.) |
| 51% | NINASIMONE | 10 | Blues singer honored with a 2017 Grammy Lifetime Achievement Award (2 wds.) |
| 51% | SHIRLEYCAESAR | 13 | Gospel singer honored with a 2017 Grammy Lifetime Achievement Award (2 wds.) |
| 50% | MAHALIAJACKSON | 14 | Gospel singer honored with a Grammy Lifetime Achievement Award in 1972 whose last name is a city in Mississippi (2 wds.) |
| 49% | KENNEDYCENTER | 13 | Where Rita Moreno (born December 11, 1931) was honored with a Lifetime Artistic Achievement Award in 2015 (2 wds.) |
| 47% | TAMMYWYNETTE | 12 | "Stand by Your Man" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 45% | ETTA | 4 | Singer James honored with a Grammy Lifetime Achievement Award in 2003 |
| 44% | TAKINGTHE | 9 | "___ Long Way," country album by The Chicks that won a Grammy Award in 2007: 2 wds. |
| 44% | LAURIEANDERSON | 14 | "O Superman" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 43% | AHMADJAMAL | 10 | Jazz pianist honored with a Grammy Lifetime Achievement Award (2 wds.) |
| 43% | ANGELALANSBURY | 14 | Actress and singer who won six Tony Awards, including a Lifetime Achievement Tony Award in 2022 (2 wds.) |
| 43% | AHMADJAMAL | 10 | Jazz pianist honored with a 2017 Grammy Lifetime Achievement Award (2 wds.) |
| 42% | LENAHORNE | 9 | Grammy-winning singer honored with a Black Heritage U.S. postage stamp in 2018 (2 wds.) |
| 42% | ARTTATUM | 8 | Arthur, a blind 20th century jazz pianist, who was honored with a posthumous Grammy Lifetime Achievement Award in 1989: 2 wds. |
| 42% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 41% | SMOKEYROBINSON | 14 | "The Tears of a Clown" singer who received the BET Lifetime Achievement Award in 2015: 2 wds. |
| 40% | GEORGSOLTI | 10 | Hungarian-British artist who holds the record for the most Grammy Awards won in a lifetime, with 31: 2 wds. |
| 40% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 38% | ANITABAKER | 10 | "Sweet Love" singer who received the BET Lifetime Achievement Award in 2018: 2 wds. |
| 38% | EARL | 4 | Banjo player Scruggs honored with a Grammy Lifetime Achievement Award in 2008 |
| 38% | BETTYWHITE | 10 | Actress honored with a Lifetime Achievement Emmy Award who turned 99 on January 17, 2021 (2 wds.) |
| 38% | WHITNEYHOUSTON | 14 | Singer played by Naomi Ackie in the 2022 musical biopic "I Wanna Dance with Somebody" (2 wds.) |
| 38% | DOLLYPARTON | 11 | "Jolene" singer who received the CMAs' Willie Nelson Lifetime Achievement Award in 2016: 2 wds. |
| 38% | LETSMAKELOVE | 12 | Duet by Faith Hill and Tim McGraw, released in 2000, that won the couple a Grammy for Best Country Collaboration with Vocals: 3 wds. |
| 38% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |