| 100% | KENNYROGERS | 11 | Country Music Hall of Fame singer who collaborated with 17-Across and 28-Across (2 wds.) |
| 87% | EMMYLOUHARRIS | 13 | Country Music Hall of Fame singer who collaborated with 28-Across and 43-Across on the Grammy-winning 1987 album "Trio" (2 wds.) |
| 82% | DOLLYPARTON | 11 | Country Music Hall of Fame singer who collaborated with 15-Across and 43-Across on "Trio" (2 wds.) |
| 73% | LINDARONSTADT | 13 | Rock and Roll Hall of Fame singer who collaborated with 15-Across and 28-Across on "Trio" (2 wds.) |
| 69% | DOLLYPARTON | 11 | Country Music Hall of Fame singer who covers "Every Breath You Take" with Sting and "Open Arms" with Steve Perry on 48-Across (2 wds.) |
| 69% | 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.) |
| 60% | THOMASRHETT | 11 | Singer/songwriter who collaborated with 17-Across, 28-Across, Reba McEntire, and Keith Urban on the country hit "Be a Light" (2 wds.) |
| 59% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |
| 57% | LORETTALYNN | 11 | Country Music Hall of Fame singer-songwriter who passed away in 2022 (2 wds.) |
| 55% | KENNYROGERS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Country Single a record five times (2 wds.) |
| 55% | PATSYCLINE | 10 | American singer (birthday today) who was the first female solo artist inducted to the Country Music Hall of Fame: 2 wds. |
| 54% | GARTHBROOKS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Male Country Artist a record eight times (2 wds.) |
| 54% | REBAMCENTIRE | 12 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Female Country Artist a record 11 times (2 wds.) |
| 52% | DOLLYPARTON | 11 | "Jolene" singer who was inducted into the Country Music Hall of Fame in 1999: 2 wds. |
| 51% | DIERKSBENTLEY | 13 | Singer of 15-Across and 29-Across who was honored with an Academy of Country Music's Merle Haggard Spirit Award (2 wds.) |
| 51% | LORETTALYNN | 11 | "Coal Miner's Daughter" singer who was inducted into the Country Music Hall of Fame in 1988: 2 wds. |
| 51% | ANDRAECROUCH | 12 | "Soon and Very Soon" singer who was inducted into the Gospel Music Hall of Fame in 1998: 2 wds. |
| 50% | HAKEEMOLAJUWON | 14 | Hall of Fame center who signed with the Raptors in 2001 after 17 seasons with the Rockets: 2 wds. |
| 50% | JEFFBECK | 8 | 2009 Rock and Roll Hall of Fame inductee who was a guitarist with the Yardbirds: 2 wds. |
| 50% | HARLANHOWARD | 12 | Songwriter in the Nashville Songwriters, Country Music, and Songwriters Halls of Fame who wrote the songs on 40-Across's 2023 album (2 wds.) |
| 50% | TAMMYWYNETTE | 12 | "D-I-V-O-R-C-E" singer who was inducted into the Country Music Hall of Fame in 1998: 2 wds. |
| 49% | GLENCAMPBELL | 12 | "Rhinestone Cowboy" singer in the Country Music Hall of Fame (2 wds.) |
| 48% | NORAROBERTS | 11 | Romance Writers of America Hall of Fame novelist who wrote 17-Across and 29-Across (2 wds.) |
| 48% | EMMYLOUHARRIS | 13 | "Blue Kentucky Girl" singer in the Country Music Hall of Fame (2 wds.) |
| 48% | GEORGESTRAIT | 12 | "Love Without End, Amen" singer in the Country Music Hall of Fame (2 wds.) |
| 47% | PAULMCCARTNEY | 13 | 15-Across and 31-Across singer/songwriter with 18 Grammy Awards, an Academy Award, and two inductions into the Rock and Roll Hall of Fame who turns 80 years old this week (2 wds.) |
| 47% | CLYDEMCPHATTER | 14 | Singer inducted into the Rock and Roll Hall of Fame as a solo artist in 1987 and with the Drifters in 1988: 2 wds. |
| 47% | ALAN | 4 | Singer Jackson who's in the Country Music Hall of Fame |
| 46% | RAVISHANKAR | 11 | Sitar maestro who collaborated with "The Beatles" and who is the father of multiple Grammy-winning singer Norah Jones: 2 wds. |
| 46% | JASONALDEAN | 11 | 17-Across and 30-Across country singer who was named ACM's Artist of the Decade for the 2010s (2 wds.) |