| 100% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was the first Black country artist to cohost the CMA Awards (1975) and the ACM Awards (1980): 2 wds. |
| 62% | DARIUSRUCKER | 12 | "Wagon Wheel" singer who was the second Black country artist to cohost the CMA Awards (2020): 2 wds. |
| 61% | MICKEYGUYTON | 12 | "Black Like Me" singer who was the second Black country artist to cohost the ACM Awards (2021): 2 wds. |
| 51% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was honored with the 1972 Grammy Award for Best Male Country Vocal Performance (2 wds.) |
| 48% | SIDNEYPOITIER | 13 | 15-Across, 30-Across, and "Lilies of the Field" star who was the first Black man to win an Academy Award for Best Actor (2 wds.) |
| 46% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who received the Willie Nelson Lifetime Achievement Award in 2020: 2 wds. |
| 43% | PATSYCLINE | 10 | American singer (birthday today) who was the first female solo artist inducted to the Country Music Hall of Fame: 2 wds. |
| 41% | STEPHENSTILLS | 13 | American singer and songwriter who is the first artist to be inducted twice on the same night into the Rock and Roll Hall of Fame: 2 wds. |
| 39% | MEGHANTRAINOR | 13 | "All About the Bass" And "Lips Are Movin" singer who won the 2016 Best New Artist Grammy Award (2 wds.) |
| 39% | HARLANCOBEN | 11 | 17-Across and 30-Across novelist who is the first writer to win an Anthony Award, a Shamus Award, and an Edgar Award (2 wds.) |
| 38% | LEANNRIMES | 10 | Singer who is the youngest ever individual artist to win the Grammy: 2 wds. |
| 38% | JASONALDEAN | 11 | 17-Across and 30-Across country singer who was named ACM's Artist of the Decade for the 2010s (2 wds.) |
| 38% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 37% | JELLYROLL | 9 | "Need a Favor" country singer who was nominated for Best New Artist at the 2024 Grammys: 2 wds. |
| 37% | ETHELWATERS | 11 | Harlem Renaissance singer and actress who was the first African American to star in her own TV show: 2 wds. |
| 37% | JENNIFERLOPEZ | 13 | 15-Across and 27-Across singer who was the first woman honored with a "Billboard" Icon Award (2 wds) |
| 36% | STEVIENICKS | 11 | American singer and songwriter who became the first woman to be inducted twice into the Rock and Roll Hall of Fame: 2 wds. |
| 36% | JENNIFERLOPEZ | 13 | "I'm Real" pop singer who received the 2018 MTV Video Vanguard Award, the first Latin artist to do so: 2 wds. |
| 36% | NICOLEKIDMAN | 12 | "Moulin Rouge!" and "The Hours" star who was the first Australian to win an Oscar for Best Actress and the first to be nominated in consecutive years (2 wds.) |
| 36% | SOLANGEKNOWLES | 14 | 12-Across and 28-Across singer who was the first recipient of the "Billboard" Women in Music Impact Award (2 wds.) |
| 35% | LAURYNHILL | 10 | "Everything Is Everything" singer who received the Grammys for both Album of the Year and Best New Artist in 1999: 2 wds. |
| 35% | THEWEEKND | 9 | Canadian singer with an oddly spelled stage name who was the Top R&B Male Artist at the 2019 Billboard Music Awards (2 wds.) |
| 35% | LUPITANYONGO | 12 | "12 Years a Slave," 18-Across, and 32-Across star who was the first Kenyan-Mexican actress to win an Oscar (2 wds.) |
| 35% | ALICIAKEYS | 10 | "Girl on Fire" singer/pianist who was the first woman to have an "MTV Unplugged" album debut at #1 (2 wds.) |
| 34% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |
| 34% | PHOEBEBRIDGERS | 14 | 16-Across and 31-Across singer who was nominated for a 2020 Best New Artist Grammy Award (2 wds.) |
| 34% | DOJACAT | 7 | 13-Across, 19-Across, and 38-Across singer who was named New Artist of the Year at the 2020 American Music Awards (2 wds.) |
| 34% | DOLLYPARTON | 11 | Country singer who received the Gary Haber Lifting Lives Award at the 11th Annual ACM Honors: 2 wds. |
| 34% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 34% | 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. |