| 100% | REGINABELLE | 11 | "Baby Come to Me" singer who collaborated with 44-Across on the R&B hits "Without You" and 34-Across (2 wds.) |
| 51% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 51% | ALISONKRAUSS | 12 | "When You Say Nothing At All" singer who collaborated with Brad Paisley on the 2004 country hit "Whiskey Lullaby": 2 wds. |
| 47% | 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.) |
| 47% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 47% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 46% | LOUISARMSTRONG | 14 | Jazz singer and trumpeter who collaborated with 34-Across on three albums, including "Porgy and Bess": 2 wds. |
| 46% | SHERYLCROW | 10 | "All I Wanna Do" singer who collaborated with Kid Rock on his biggest pop hit, "Picture," in 2002: 2 wds. |
| 45% | NATALIECOLE | 11 | R&B singer with the hits "Our Love" and "Miss You Like Crazy" (1950-2015): 2 wds. |
| 45% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 45% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 44% | LANADELREY | 10 | "Doin' Time" singer who collaborates with 27-Across and 35-Across on the 2019 "Charlie's Angels" theme song "Don't Call Me Angel" (3 wds.) |
| 44% | IGGYAZALEA | 10 | "Fancy" singer featured on "Problem" who in 2014 became the second ever to be simultaneously #1 and #2 with her first two hits: 2 wds. |
| 44% | 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.) |
| 42% | SEANPAUL | 8 | Rapper who collaborated with Beyoncé on the 2003 #1 hit "Baby Boy": 2 wds. |
| 42% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 41% | THEWEEKND | 9 | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| 40% | KANEBROWN | 9 | R&B and country singer with the 2022 country hit "Thank God": 2 wds. |
| 40% | THEBEATLES | 10 | "I Want to Hold Your Hand" and "She Loves You" group who in 1964 became the first ever to be simultaneously #1 and #2 with their first two hits: 2 wds. |
| 40% | MEGANTHEE | 9 | With 46-Across, rapper who collaborated with Beyoncé on the 2020 #1 hit "Savage (Remix)": 2 wds. |
| 40% | DOLLYPARTON | 11 | Country Music Hall of Fame singer who collaborated with 15-Across and 43-Across on "Trio" (2 wds.) |
| 40% | LINDARONSTADT | 13 | Rock and Roll Hall of Fame singer who collaborated with 15-Across and 28-Across on "Trio" (2 wds.) |
| 40% | THEWEEKND | 9 | "The Hills" R&B singer who got his seventh #1 hit with 38-Across: 2 wds. |
| 40% | PETERFRAMPTON | 13 | "I'm in You" singer with the hit single "Baby, I Love Your Way": 2 wds. |
| 39% | SHAWNMENDES | 11 | "Treat You Better" folk-pop singer who partnered with Justin Bieber on the 2020 top 10 song "Monster": 2 wds. |
| 39% | SUMMERSIXTEEN | 13 | 2016 Drake hit that went to #1 on the Billboard R&B and Rap charts: 2 wds. |
| 39% | HOTLINEBLING | 12 | 2015 Drake hit that went to #1 on the Billboard R&B and Rap charts: 2 wds. |
| 39% | MICHAELSTIPE | 12 | Singer who came up with "It's the End of the World as We Know It (And I Feel Fine)" in his sleep: 2 wds. |
| 38% | NORAHJONES | 10 | "Come Away With Me" singer who received the Grammys for both Album of the Year and Best New Artist in 2003: 2 wds. |
| 38% | MORGANWALLEN | 12 | Country singer who's also topped the Hot R&B/Hip-Hop chart, thanks to "Broadway Girls" with Lil Durk: 2 wds. |