| 100% | KENNYCHESNEY | 12 | Country singer whose marriage to Renée Zellweger was annulled after just four months: 2 wds. |
| 40% | MARIO | 5 | With 33-Across, "Access Hollywood" host whose marriage to Ali Landry was annulled after just 18 days |
| 38% | DOLLYPARTON | 11 | Country singer whose latest album, "I Believe In You," is geared toward children: 2 wds. |
| 36% | LUKECOMBS | 9 | Country singer whose cover of 27-Across's "Fast Car" was a #2 hit in 2023: 2 wds. |
| 36% | CHADKROEGER | 11 | Nickelback lead singer whose first name is an African country: 2 wds. |
| 35% | SINEADOCONNOR | 13 | Singer whose "Nothing Compares 2 U" was a #1 song for four weeks in 1990 (2 wds.) |
| 35% | PAULACOLE | 9 | Singer whose "I Don't Want to Wait" was the theme song for "Dawson's Creek": 2 wds. |
| 33% | KEITHURBAN | 10 | Country singer who was an "American Idol" judge for four seasons: 2 wds. |
| 33% | FAITHHILL | 9 | Country singer whose song "Breathe" was named the #1 single on Billboard's year-end countdown in 2000 (2 wds.) |
| 32% | HARRYSTYLES | 11 | "As It Was" singer whose 2022 album generated four simultaneous top 10 hits: 2 wds. |
| 32% | RANDYNEWMAN | 11 | Singer whose song "I Love L.A." is played after home victories at Dodgers Stadium (2 wds.) |
| 32% | ELTONJOHN | 9 | Singer whose "Farewell Yellow Brick Road" tour is the third highest-grossing concert tour of all time, after Coldplay's "Music of the Spheres": 2 wds. |
| 32% | FAITHHILL | 9 | "Speak to a Girl" singer whose first name is a positive virtue (belief): 2 wds. |
| 32% | THOMASRHETT | 11 | Country singer whose album "Life Changes" topped the Billboard 200 in 2017: 2 wds. |
| 31% | LUKECOMBS | 9 | "Forever After All" country singer whose "The Kind of Love We Make" hit the Billboard Top 10 in 2022: 2 wds. |
| 31% | VINCEGILL | 9 | Country singer who's married to singer Amy Grant: 2 wds. |
| 31% | FAITHHILL | 9 | Country singer who's married to singer Tim McGraw: 2 wds. |
| 31% | KEITHURBAN | 10 | Country singer who's married to actress Nicole Kidman: 2 wds. |
| 31% | JASONALDEAN | 11 | Country singer whose album "They Don't Know" topped the Billboard 200 in 2016: 2 wds. |
| 31% | CLINTBLACK | 10 | Country singer who's married to singer/actress Lisa Hartman: 2 wds. |
| 31% | ALGREEN | 7 | Singer whose name is an anagram of the word "general": 2 wds. |
| 31% | BRETTELDREDGE | 13 | Country singer whose "Baby, It's Cold Outside" topped the Adult Contemporary chart in 2017: 2 wds. |
| 31% | DENNISRODMAN | 12 | Former NBA player who was divorced from Carmen Electra after just five months: 2 wds. |
| 30% | HARRYSTYLES | 11 | Singer whose "As It Was" was the best-selling global single of 2022: 2 wds. |
| 30% | CHRISSTAPLETON | 14 | Singer whose "Starting Over" won the Grammy for Best Country Album in 2022: 2 wds. |
| 30% | JOHNNYCASH | 10 | Country singer who was the subject of the 2005 biopic "Walk the Line": 2 wds. |
| 30% | EDSHEERAN | 9 | Singer whose "÷ Tour" is the fourth highest-grossing concert tour of all time: 2 wds. |
| 30% | TAYLORSWIFT | 11 | Singer whose "Eras Tour" is the highest-grossing concert tour of all time: 2 wds. |
| 30% | MILEYCYRUS | 10 | Singer whose 2008 album "Breakout" hit #1 when she was 15: 2 wds. |
| 30% | PATSYCLINE | 10 | Country singer with the 1961 crossover hit "I Fall to Pieces": 2 wds. |