| 100% | JAMESOTTO | 9 | "Just Got Started Lovin' You" country singer who served two years in the Navy: 2 wds. |
| 61% | ZACHBRYAN | 9 | "Something in the Orange" country singer who served eight years in the Navy: 2 wds. |
| 54% | JAMEYJOHNSON | 12 | "In Color" country singer who served four years in the Marine Corps Reserve: 2 wds. |
| 41% | ORVILLEPECK | 11 | Country singer who played the Emcee in "Cabaret" after 18-Across: 2 wds. |
| 40% | ELVISPRESLEY | 12 | "Blue Suede Shoes" singer who served in the US Army from 1958 to 1960: 2 wds. |
| 40% | JIMIHENDRIX | 11 | "Purple Haze" singer who served in the US Army from 1961 to 1962: 2 wds. |
| 39% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 39% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 38% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 38% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 37% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 37% | BOBDYLAN | 8 | "Blowin' in the Wind" singer-songwriter who was awarded the Nobel Prize in Literature in the year 2016: 2 wds. |
| 37% | KELLYCLARKSON | 13 | "Since U Been Gone" singer who voices Delta Dawn, leader of the Country Trolls, in "Trolls World Tour": 2 wds. |
| 36% | TEDWILLIAMS | 11 | Hall of Fame Red Sox legend who served in the US Navy and Marine Corps during World War II: 2 wds. |
| 36% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 36% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 36% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 36% | REBAMCENTIRE | 12 | Red-haired country singer who's in her first season as a coach on "The Voice": 2 wds. |
| 36% | TIMMCGRAW | 9 | Country singer who collapsed from dehydration while onstage in Dublin: 2 wds. |
| 35% | MARENMORRIS | 11 | "The Bones" country singer who won Female Vocalist of the Year at the 2020 CMAs: 2 wds. |
| 35% | LYNDONJOHNSON | 13 | 36th US president, who served in the Navy during World War II: 2 wds. |
| 35% | RICHARDNIXON | 12 | 37th US president, who served in the Navy during World War II: 2 wds. |
| 35% | TANYATUCKER | 11 | "Delta Dawn" country singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 35% | STEVIEWONDER | 12 | Singer who won the Oscar for Best Original Song, "Just Called to Say I Love You": 2 wds. |
| 35% | BLAKESHELTON | 12 | "Nobody but You" country singer who's been a coach on "The Voice" since 2011: 2 wds. |
| 35% | ARIANAGRANDE | 12 | "Yes, And?" singer who had two songs reach #1 on the Billboard Hot 100 in 2024: 2 wds. |
| 35% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 35% | JOHNNYCASH | 10 | Country singer who was the subject of the 2005 biopic "Walk the Line": 2 wds. |
| 35% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 34% | QUEENLATIFAH | 12 | Singer who played the Wiz in "The Wiz Live!": 2 wds. |