| 100% | TIMMCGRAW | 9 | Country singer who collapsed from dehydration while onstage in Dublin: 2 wds. |
| 43% | ORVILLEPECK | 11 | Country singer who played the Emcee in "Cabaret" after 18-Across: 2 wds. |
| 41% | JAMESOTTO | 9 | "Just Got Started Lovin' You" country singer who served two years in the Navy: 2 wds. |
| 40% | JAMEYJOHNSON | 12 | "In Color" country singer who served four years in the Marine Corps Reserve: 2 wds. |
| 40% | REBAMCENTIRE | 12 | Red-haired country singer who's in her first season as a coach on "The Voice": 2 wds. |
| 40% | TAYLORSWIFT | 11 | Pop singer who pulled her entire catalog from Spotify in November 2014: 2 wds. |
| 39% | JIMIHENDRIX | 11 | "Purple Haze" singer who served in the US Army from 1961 to 1962: 2 wds. |
| 39% | TOBYKEITH | 9 | "Made in America" country singer who owns racehorses: 2 wds. |
| 39% | ELVISPRESLEY | 12 | "Blue Suede Shoes" singer who served in the US Army from 1958 to 1960: 2 wds. |
| 38% | GERIHALLIWELL | 13 | Singer who had four #1 hits in the UK from 1999 to 2001, including "It's Raining Men": 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. |
| 37% | CLINTBLACK | 10 | Country singer who's married to singer/actress Lisa Hartman: 2 wds. |
| 37% | VINCEGILL | 9 | Country singer who's married to singer Amy Grant: 2 wds. |
| 37% | FAITHHILL | 9 | Country singer who's married to singer Tim McGraw: 2 wds. |
| 36% | ZACHBRYAN | 9 | "Something in the Orange" country singer who served eight years in the Navy: 2 wds. |
| 36% | KEITHURBAN | 10 | Country singer who was an "American Idol" judge for four seasons: 2 wds. |
| 36% | CHRISTIANKANE | 13 | Country singer who portrays an art/architecture expert on 15-Across: 2 wds. |
| 36% | TANYATUCKER | 11 | "Delta Dawn" country singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 35% | DOLLYPARTON | 11 | Country singer who coauthored 2022's "Run, Rose, Run" with 31-Across: 2 wds. |
| 35% | TIMMCGRAW | 9 | American country singer and actor from "The Blind Side" who holds a pilot license and owns a Cirrus SR22: 2 wds. |
| 35% | AMBERRILEY | 10 | Singer who played Addaperle in "The Wiz Live!": 2 wds. |
| 35% | GARTHBROOKS | 11 | Country singer who has not made his music available on Spotify or iTunes: 2 wds. |
| 35% | JOHNNYCASH | 10 | Country singer who was the subject of the 2005 biopic "Walk the Line": 2 wds. |
| 35% | KEITHURBAN | 10 | Country singer who's married to actress Nicole Kidman: 2 wds. |
| 35% | QUEENLATIFAH | 12 | Singer who played the Wiz in "The Wiz Live!": 2 wds. |
| 35% | DIANAROSS | 9 | Singer who played Dorothy in 1978's "The Wiz": 2 wds. |
| 35% | TRISHAYEARWOOD | 14 | Country singer who, along with her husband, helps build houses for Habitat for Humanity: 2 wds. |
| 34% | TENDERMERCIES | 13 | 1983 movie about a washed-up country singer who finds new love: 2 wds. |
| 34% | JIMMIEALLEN | 11 | "Best Shot" country singer who came in seventh place with partner Emma Slater on season 30 of "Dancing with the Stars" (2 wds.) |
| 34% | BADBUNNY | 8 | Puerto Rican singer who acted in the film "Bullet Train": 2 wds. |