| 100% | ALISONKRAUSS | 12 | "When You Say Nothing At All" singer who collaborated with Brad Paisley on the 2004 country hit "Whiskey Lullaby": 2 wds. |
| 60% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 57% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 49% | ALISONKRAUSS | 12 | "When You Say Nothing at All" country singer who has won 27 Grammys: 2 wds. |
| 41% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 40% | REGINABELLE | 11 | "Baby Come to Me" singer who collaborated with 44-Across on the R&B hits "Without You" and 34-Across (2 wds.) |
| 39% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 39% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 39% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 39% | THOMASRHETT | 11 | Singer/songwriter who collaborated with 17-Across, 28-Across, Reba McEntire, and Keith Urban on the country hit "Be a Light" (2 wds.) |
| 34% | SHERYLCROW | 10 | "All I Wanna Do" singer who collaborated with Kid Rock on his biggest pop hit, "Picture," in 2002: 2 wds. |
| 34% | RONAN | 5 | "When You Say Nothing at All" singer Keating |
| 34% | SEANPAUL | 8 | Rapper who collaborated with Beyoncé on the 2003 #1 hit "Baby Boy": 2 wds. |
| 34% | EMMYLOUHARRIS | 13 | Country Music Hall of Fame singer who collaborated with 28-Across and 43-Across on the Grammy-winning 1987 album "Trio" (2 wds.) |
| 33% | STEVIEWONDER | 12 | Singer who signed with record company Motown when he was 11 and gave his first number-one hit at 13: 2 wds. |
| 32% | ESTELLE | 7 | British singer who collaborated with Kanye West on the 2008 hit "American Boy" |
| 31% | THEWEEKND | 9 | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| 31% | CHRISSTAPLETON | 14 | "Tennessee Whiskey" country singer who sang the National Anthem at the 2023 Super Bowl: 2 wds. |
| 31% | ERIC | 4 | Singer Church who duetted with Keith Urban on the #1 country hit "Raise 'Em Up" |
| 30% | DOLLYPARTON | 11 | Country Music Hall of Fame singer who collaborated with 15-Across and 43-Across on "Trio" (2 wds.) |
| 30% | MEGANTHEE | 9 | With 46-Across, rapper who collaborated with Beyoncé on the 2020 #1 hit "Savage (Remix)": 2 wds. |
| 30% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 30% | TODDRUNDGREN | 12 | Singer who came up with "Bang the Drum All Day" in his sleep: 2 wds. |
| 30% | SHEENAEASTON | 12 | "Strut" singer who Prince encouraged and collaborated with in the 1980s: 2 wds. |
| 30% | ATALL | 5 | "When You Say Nothing ___" (Ronan Keating's 1999 hit song): 2 wds. |
| 30% | REBA | 4 | Country singer McEntire with the hit "I Keep On Loving You" |
| 30% | SHAWNMENDES | 11 | "Treat You Better" folk-pop singer who partnered with Justin Bieber on the 2020 top 10 song "Monster": 2 wds. |
| 30% | BRETTELDREDGE | 13 | "Somethin' I'm Good At" singer who topped the Billboard Country Albums chart with his latest LP: 2 wds. |
| 30% | PAULSIMON | 9 | Singer who performed "Still Crazy After All These Years" on the SNL40 anniversary special: 2 wds. |
| 30% | RAVISHANKAR | 11 | Sitar maestro who collaborated with "The Beatles" and who is the father of multiple Grammy-winning singer Norah Jones: 2 wds. |