| 100% | TIM | 3 | "The Cowboy in Me" singer ___ McGraw |
| 66% | TIM | 3 | ___ McGraw who sang "The Cowboy in Me" |
| 59% | ROSS | 4 | "Touch Me in the Morning" singer Diana |
| 59% | SHANIA | 6 | "The Woman in Me" singer Twain |
| 59% | SHANIA | 6 | “The Woman in Me” singer Twain |
| 58% | KIKIDEE | 7 | "I've Got the Music in Me" singer, 1974 |
| 56% | DESTINY | 7 | "Je me casse" singer who represented Malta in the 2021 Eurovision |
| 55% | GLENCAMPBELL | 12 | "Rhinestone Cowboy" singer in the Country Music Hall of Fame (2 wds.) |
| 54% | RAYCHARLES | 10 | "What'd I Say" singer whose sunglasses are in the Smithsonian (2 wds.) |
| 53% | JOHNLEGEND | 10 | "All of Me" singer who wrote a song in "SpongeBob SquarePants: The Broadway Musical": 2 wds. |
| 52% | REBAMCENTIRE | 12 | "Consider Me Gone" country singer recognized by the Kennedy Center Honors in 2018 (2 wds.) |
| 52% | TODDRUNDGREN | 12 | "Hello It's Me" singer inducted into the Rock and Roll Hall of Fame in 2021: 2 wds. |
| 52% | ANNEMURRAY | 10 | "You Needed Me" singer who was made a Companion of the Order of Canada in 1984: 2 wds. |
| 51% | SHANIA | 6 | ___ Twain, "Man! I Feel Like a Woman" country singer who made her breakthrough in the '90s |
| 51% | ETTA | 4 | "Trust in Me" singer James |
| 51% | ELSA | 4 | "The cold never bothered me anyway" singer in "Frozen" |
| 51% | ROMO | 4 | Quarterback Tony who joined the Cowboys in 2003 |
| 51% | PETESEEGER | 10 | "If I Had a Hammer" folk singer who received the Woody Guthrie Prize in 2014: 2 wds. |
| 50% | PETERFRAMPTON | 13 | "I'm in You" singer with the hit single "Baby, I Love Your Way": 2 wds. |
| 50% | WOODY | 5 | Cowboy in the "Toy Story" films |
| 50% | MITSKI | 6 | Be the Cowboy singer |
| 50% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 50% | LEANNRIMES | 10 | Singer whose "How Do I Live" spent 32 weeks in the Billboard Top 10 in 1997 and 1998: 2 wds. |
| 50% | ELVISPRESLEY | 12 | "Love Me Tender" singer who was inducted into the Gospel Music Hall of Fame in 2001: 2 wds. |
| 50% | LIZZO | 5 | "I put the sing in single" singer |
| 49% | TIMBERLAKE | 10 | Justin ___, "Cry Me a River" singer who starred in the variety TV show "The All New Mickey Mouse Club" |
| 49% | HIATT | 5 | "Have a Little Faith in Me" singer John |
| 49% | MAC | 3 | "Here Comes the Cowboy" singer DeMarco |
| 48% | SIREN | 5 | Singer in the "Odyssey" |
| 48% | RAT | 3 | Singer in the family? |