| 100% | GARTHBROOKS | 11 | Country music star honored by the 32-Across with a Lifetime Artistic Achievement Award in 2021 (2 wds.) |
| 81% | DEBBIEALLEN | 11 | Dancer/choreographer/actress honored by the 32-Across with a Lifetime Artistic Achievement Award in 2021 (2 wds.) |
| 66% | GLADYSKNIGHT | 12 | Grammy-winning singer honored by the 50-Across with a Lifetime Artistic Achievement Award in 2022 (2 wds.) |
| 66% | GEORGECLOONEY | 13 | Oscar-winning actor honored by the 50-Across with a Lifetime Artistic Achievement Award in 2022 (2 wds.) |
| 48% | KENNEDYCENTER | 13 | Where Rita Moreno (born December 11, 1931) was honored with a Lifetime Artistic Achievement Award in 2015 (2 wds.) |
| 43% | DOLLYPARTON | 11 | Country music star who sang "Islands in the Stream" with 36-Across (2 wds.) |
| 42% | BETTYWHITE | 10 | Actress honored with a Lifetime Achievement Emmy Award who turned 99 on January 17, 2021 (2 wds.) |
| 38% | CONWAYTWITTY | 12 | Country Music Hall of Fame singer who shared four consecutive CMA Awards for Vocal Duo of the Year with 28-Across in the 1970s (2 wds.) |
| 38% | MAHALIAJACKSON | 14 | Gospel singer honored with a Grammy Lifetime Achievement Award in 1972 whose last name is a city in Mississippi (2 wds.) |
| 37% | LAINEYWILSON | 12 | 2021 Academy of Country Music Awards New Artist of the Year who sings 30-Across with 40-Across (2 wds.) |
| 37% | JOHNNYCASH | 10 | Country music legend honored on a postage stamp in 2013: 2 wds. |
| 36% | NINASIMONE | 10 | Blues singer honored with a Grammy Lifetime Achievement Award (2 wds.) |
| 36% | SHIRLEYCAESAR | 13 | Gospel singer honored with a Grammy Lifetime Achievement Award (2 wds.) |
| 36% | AHMADJAMAL | 10 | Jazz pianist honored with a Grammy Lifetime Achievement Award (2 wds.) |
| 36% | DOLLYPARTON | 11 | Country music star with a January birthday (2 wds.) |
| 36% | NINASIMONE | 10 | Blues singer honored with a 2017 Grammy Lifetime Achievement Award (2 wds.) |
| 36% | SHIRLEYCAESAR | 13 | Gospel singer honored with a 2017 Grammy Lifetime Achievement Award (2 wds.) |
| 36% | AHMADJAMAL | 10 | Jazz pianist honored with a 2017 Grammy Lifetime Achievement Award (2 wds.) |
| 35% | ARTTATUM | 8 | Arthur, a blind 20th century jazz pianist, who was honored with a posthumous Grammy Lifetime Achievement Award in 1989: 2 wds. |
| 35% | JOSEFELICIANO | 13 | "Feliz Navidad" singer who received the Billboard Latin Music Lifetime Achievement Award in 1996: 2 wds. |
| 35% | TAMMYWYNETTE | 12 | "Stand by Your Man" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 35% | JOHNBOYEGA | 10 | "Star Wars: The Force Awakens" actor honored with a BAFTA Rising Star Award in 2016 (2 wds.) |
| 34% | EMILIOESTEFAN | 13 | Miami Sound Machine musician who received the Billboard Latin Music Lifetime Achievement Award in 1994: 2 wds. |
| 34% | SMOKEYROBINSON | 14 | "The Tears of a Clown" singer who received the BET Lifetime Achievement Award in 2015: 2 wds. |
| 34% | CARLOSSANTANA | 13 | "Oye Como Va" musician who received the Billboard Latin Music Lifetime Achievement Award in 2009: 2 wds. |
| 34% | CRAIGT | 6 | With 32-Across, "Coach" star who played the father in the 1982 version of 18-Across: 2 wds. |
| 34% | COLESWINDELL | 12 | 2015 Academy of Country Music Awards New Artist of the Year who sings 30-Across with 18-Across (2 wds.) |
| 34% | DIANA | 5 | Ross who received a Lifetime Achievement Award at the American Music Awards, which were hosted by her daughter Tracee Ellis Ross |
| 33% | TANYATUCKER | 11 | "Delta Dawn" country singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 33% | TAKINGTHE | 9 | "___ Long Way," country album by The Chicks that won a Grammy Award in 2007: 2 wds. |