| 100% | GEORGEJONES | 11 | "He Stopped Loving Her Today" country singer recognized by the Kennedy Center Honors in 2008 (2 wds.) |
| 63% | REBAMCENTIRE | 12 | "Consider Me Gone" country singer recognized by the Kennedy Center Honors in 2018 (2 wds.) |
| 62% | WILLIENELSON | 12 | "Always on My Mind" country singer recognized by the Kennedy Center Honors in 1998 (2 wds.) |
| 49% | JUSTINODIAZ | 11 | Puerto Rican opera singer celebrated by the Kennedy Center Honors in 2021 (2 wds.) |
| 48% | JONIMITCHELL | 12 | Canadian singer/songwriter celebrated by the Kennedy Center Honors in 2021 (2 wds.) |
| 44% | DIONNEWARWICK | 13 | "Walk on By" singer honored by the Kennedy Center in 2023 (2 wds.) |
| 40% | BETTEMIDLER | 11 | American star of stage and screen celebrated by the Kennedy Center Honors in 2021 (2 wds.) |
| 39% | QUEENLATIFAH | 12 | "Chicago" Oscar nominee honored by the Kennedy Center in 2023 (2 wds.) |
| 36% | YEHUD | 5 | Violinist recognized at the Kennedy Center Honors in 1986 |
| 36% | LORETTALYNN | 11 | Country singer played by 44-Across in the 1980 biopic "Coal Miner's Daughter": 2 wds. |
| 36% | RENEEFLEMING | 12 | "Signatures - Great Opera Scenes" soprano honored by the Kennedy Center in 2023 (2 wds.) |
| 34% | LINDARONSTADT | 13 | 15-Across and 48-Across singer recognized at the 2019 Kennedy Center Honors (2 wds.) |
| 34% | GARTHBROOKS | 11 | "The Thunder Rolls" country singer who received a 2020 Kennedy Center Honor: 2 wds. |
| 33% | PAULMCCARTNEY | 13 | "My Love" singer who received a 2010 Kennedy Center Honor: 2 wds. |
| 33% | REBAMCENTIRE | 12 | Red-haired country singer who's in her first season as a coach on "The Voice": 2 wds. |
| 33% | LIBERTYMEDAL | 12 | Annual award bestowed by the National Constitution Center to recognize leadership in the pursuit of freedom (2 wds.) |
| 32% | ORVILLEPECK | 11 | Country singer who played the Emcee in "Cabaret" after 18-Across: 2 wds. |
| 32% | TINATURNER | 10 | Singer played by Angela Bassett in the 1993 musical biopic "What's Love Got to Do with It" (2 wds.) |
| 31% | TAYLORSWIFT | 11 | Country singer who had a crossover hit with her 2008 pop song "Love Story" (2 wds.) |
| 31% | ALEXANDRADANILOVA | 17 | Prima ballerina who received the Kennedy Center Honors in 1989 |
| 31% | REBAMCENTIRE | 12 | "My Kind of Country" singer who made her film debut playing Burt's wife Heather in the first "Tremors" film (2 wds.) |
| 31% | JAMESOTTO | 9 | "Just Got Started Lovin' You" country singer who served two years in the Navy: 2 wds. |
| 30% | JAMEYJOHNSON | 12 | "In Color" country singer who served four years in the Marine Corps Reserve: 2 wds. |
| 30% | HUMANRIGHTS | 11 | Cause advanced by the nonprofit center 44-Across founded in 1982: 2 wds. |
| 30% | DOLLYPARTON | 11 | Country singer who received the Gary Haber Lifting Lives Award at the 11th Annual ACM Honors: 2 wds. |
| 30% | BRIANWILSON | 11 | Singer played by Paul Dano and John Cusack in the music biopic "Love & Mercy" (2 wds.) |
| 30% | JANETJACKSON | 12 | "Rhythm Nation" singer who received the GLAAD Vanguard Award in 2008: 2 wds. |
| 30% | LUKECOMBS | 9 | "Forever After All" country singer whose "The Kind of Love We Make" hit the Billboard Top 10 in 2022: 2 wds. |
| 30% | GEORGESTRAIT | 12 | "Love Without End, Amen" singer in the Country Music Hall of Fame (2 wds.) |
| 29% | CHRISSTAPLETON | 14 | Country singer whose album "Traveller" topped the Billboard 200 in 2015: 2 wds. |