| 100% | HOYTAXTON | 9 | "Joy to the World" country singer born in Duncan, Oklahoma (2 wds.) |
| 57% | JOEDIFFIE | 9 | "Pickup Man" country singer born in Tulsa, Oklahoma (2 wds.) |
| 54% | TOBYKEITH | 9 | "How Do You Like Me Now?!" country singer born in Clinton, Oklahoma (2 wds.) |
| 51% | VINCEGILL | 9 | "I Still Believe in You" country singer born in Norman, Oklahoma (2 wds.) |
| 48% | DOGNIGHT | 8 | Three ___ ("Joy to the World" band): 2 wds. |
| 48% | PATSYCLINE | 10 | Country singer with the 1961 crossover hit "I Fall to Pieces": 2 wds. |
| 48% | ORVILLEPECK | 11 | Country singer who played the Emcee in "Cabaret" after 18-Across: 2 wds. |
| 48% | JLO | 3 | Pop diva born in the Bronx, to her fans: 2 wds. |
| 47% | LORETTALYNN | 11 | Country singer played by 44-Across in the 1980 biopic "Coal Miner's Daughter": 2 wds. |
| 46% | JAMESOTTO | 9 | "Just Got Started Lovin' You" country singer who served two years in the Navy: 2 wds. |
| 45% | JAMEYJOHNSON | 12 | "In Color" country singer who served four years in the Marine Corps Reserve: 2 wds. |
| 44% | MORGANWALLEN | 12 | Country singer who's also topped the Hot R&B/Hip-Hop chart, thanks to "Broadway Girls" with Lil Durk: 2 wds. |
| 43% | BERLINTRILOGY | 13 | Name given to the three consecutive studio albums by singer-songwriter David Bowie which were released in the 70s: 2 wds. |
| 43% | BILLYRAYCYRUS | 13 | Country singer who's also topped the Hot R&B/Hip-Hop chart, thanks to "Old Town Road" with Lil Nas X: 2 wds. |
| 43% | WYNONNAJUDD | 11 | "I Saw the Light" country singer born May 30, 1964 (2 wds.) |
| 43% | JASONALDEAN | 11 | Country singer named ACM's Artist of the Decade for the 2010s in 2019 (2 wds.) |
| 42% | JOAQUINPHOENIX | 14 | "Joker" actor who plays country singer Johnny Cash in "Walk the Line" (2 wds.) |
| 42% | CHRISSTAPLETON | 14 | Country singer whose album "Traveller" topped the Billboard 200 in 2015: 2 wds. |
| 42% | BRINGINTO | 9 | ___ the world (give birth to): 2 wds. |
| 42% | ZACHBRYAN | 9 | "Something in the Orange" country singer who served eight years in the Navy: 2 wds. |
| 42% | REBAMCENTIRE | 12 | "Consider Me Gone" country singer recognized by the Kennedy Center Honors in 2018 (2 wds.) |
| 41% | WILLIENELSON | 12 | "Always on My Mind" country singer recognized by the Kennedy Center Honors in 1998 (2 wds.) |
| 41% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| 41% | KENNYCHESNEY | 12 | Singer of the 2007 #1 country hit "Beer in Mexico": 2 wds. |
| 41% | LOUISARMSTRONG | 14 | Jazz trumpeter and singer born in New Orleans: 2 wds. |
| 41% | GEORGEJONES | 11 | "He Stopped Loving Her Today" country singer recognized by the Kennedy Center Honors in 2008 (2 wds.) |
| 41% | UPABOVE | 7 | "___ the world so high, like a diamond in the sky": 2 wds. |
| 41% | VINCEGILL | 9 | Country singer who's married to singer Amy Grant: 2 wds. |
| 41% | FAITHHILL | 9 | Country singer who's married to singer Tim McGraw: 2 wds. |
| 41% | KEITHURBAN | 10 | Country singer who's married to actress Nicole Kidman: 2 wds. |