| 100% | LINDARONSTADT | 13 | 15-Across and 48-Across singer recognized at the 2019 Kennedy Center Honors (2 wds.) |
| 53% | KALIUCHIS | 9 | 15-Across and 32-Across singer-songwriter who was honored as the Top Latin Female Artist at the 2022 Billboard Music Awards (2 wds.) |
| 52% | REBAMCENTIRE | 12 | "Consider Me Gone" country singer recognized by the Kennedy Center Honors in 2018 (2 wds.) |
| 50% | WILLIENELSON | 12 | "Always on My Mind" country singer recognized by the Kennedy Center Honors in 1998 (2 wds.) |
| 50% | GEORGEJONES | 11 | "He Stopped Loving Her Today" country singer recognized by the Kennedy Center Honors in 2008 (2 wds.) |
| 49% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 48% | JENNIFERLOPEZ | 13 | 15-Across and 27-Across singer who was the first woman honored with a "Billboard" Icon Award (2 wds) |
| 48% | GARTHBROOKS | 11 | "The Thunder Rolls" country singer who received a 2020 Kennedy Center Honor: 2 wds. |
| 46% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 45% | NEILDIAMOND | 11 | "Cracklin' Rosie" singer who received a 2011 Kennedy Center Honor: 2 wds. |
| 45% | PAULMCCARTNEY | 13 | "My Love" singer who received a 2010 Kennedy Center Honor: 2 wds. |
| 45% | JONIMITCHELL | 12 | Canadian singer/songwriter celebrated by the Kennedy Center Honors in 2021 (2 wds.) |
| 44% | BETTEMIDLER | 11 | American star of stage and screen celebrated by the Kennedy Center Honors in 2021 (2 wds.) |
| 44% | DIONNEWARWICK | 13 | "That's What Friends Are For" singer who received a 2023 Kennedy Center Honor: 2 wds. |
| 43% | DIONNEWARWICK | 13 | "Walk on By" singer honored by the Kennedy Center in 2023 (2 wds.) |
| 43% | DEBBIEALLEN | 11 | "Fame" actress and choreographer who received a 2020 Kennedy Center Honor: 2 wds. |
| 43% | YEHUD | 5 | Violinist recognized at the Kennedy Center Honors in 1986 |
| 43% | JUSTINODIAZ | 11 | Puerto Rican opera singer celebrated by the Kennedy Center Honors in 2021 (2 wds.) |
| 42% | BRITNEYSPEARS | 13 | Singer of 15-Across and 50-Across known as the "Princess of Pop" (2 wds.) |
| 42% | JUSTINBIEBER | 12 | "Yummy" singer with the 2021 #1 song at 16-Across and the #1 album at 44-Across: 2 wds. |
| 41% | MEGANRAPINOE | 12 | US player who won the Golden Boot and the Golden Ball at the 2019 World Cup: 2 wds. |
| 41% | NIPSEYHUSSLE | 12 | Rapper and community activist whose 2019 memorial service was held at the Staples Center in Los Angeles (2 wds.) |
| 40% | QUEENLATIFAH | 12 | "The Equalizer" star who received a 2023 Kennedy Center Honor: 2 wds. |
| 40% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |
| 40% | SUSANCHOI | 9 | 15-Across and 33-Across writer who won the 2019 National Book Award for Fiction for her novel "Trust Exercise" (2 wds.) |
| 40% | JONIMITCHELL | 12 | 15-Across and 44-Across singer-songwriter who was honored with a Gershwin Award in 2023 (2 wds.) |
| 40% | SARABAREILLES | 13 | 15-Across and 49-Across singer/songwriter whose new album "Amidst the Chaos" was released this month (2 wds.) |
| 39% | DRAKE | 5 | Singer of 15-Across, 28-Across, and 38-Across who was honored with the Artist of the Decade Award at the 2021 "Billboard" Music Awards |
| 39% | EDDIEREDMAYNE | 13 | "The Theory of Everything" star who was a schoolmate of 15-Across and 47-Across at Eton College: 2 wds. |
| 39% | DIERKSBENTLEY | 13 | Singer of "Home" and 15-Across: 2 wds. |