| 100% | LOUISARMSTRONG | 14 | Jazz singer and trumpeter who collaborated with 34-Across on three albums, including "Porgy and Bess": 2 wds. |
| 47% | REGINABELLE | 11 | "Baby Come to Me" singer who collaborated with 44-Across on the R&B hits "Without You" and 34-Across (2 wds.) |
| 46% | 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.) |
| 43% | DOLLYPARTON | 11 | Country Music Hall of Fame singer who collaborated with 15-Across and 43-Across on "Trio" (2 wds.) |
| 42% | LINDARONSTADT | 13 | Rock and Roll Hall of Fame singer who collaborated with 15-Across and 28-Across on "Trio" (2 wds.) |
| 42% | 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.) |
| 41% | BEBEREXHA | 9 | Singer who performed on 15-, 27-, and 34-Across: 2 wds. |
| 40% | THENATIONAL | 11 | "Fake Empire" indie rock band who collaborated with 19-Across, 32-Across, and Sufjan Stevens on the 2023 album "First Two Pages of Frankenstein" (2 wds.) |
| 40% | BILLYPRESTON | 12 | Singer who sang with Nat King Cole on a TV show at 11 and released his first album at 16: 2 wds. |
| 39% | THEWEEKND | 9 | Singer who collaborated with Ariana Grande on their 2014 top 10 song "Love Me Harder": 2 wds. |
| 39% | CIARA | 5 | One-named singer who collaborated with Missy Elliott on "1, 2 Step" and "Lose Control" |
| 38% | KENNYROGERS | 11 | Country Music Hall of Fame singer who collaborated with 17-Across and 28-Across (2 wds.) |
| 38% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 38% | ALISONKRAUSS | 12 | "When You Say Nothing At All" singer who collaborated with Brad Paisley on the 2004 country hit "Whiskey Lullaby": 2 wds. |
| 38% | JULIAMICHAELS | 13 | "Issues" singer who's collaborated with Pink, Britney Spears, and Gwen Stefani: 2 wds. |
| 37% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 37% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 37% | 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.) |
| 37% | SHERYLCROW | 10 | "All I Wanna Do" singer who collaborated with Kid Rock on his biggest pop hit, "Picture," in 2002: 2 wds. |
| 37% | KENDRICKLAMAR | 13 | "To Pimp a Butterfly" rapper, who collaborated with Taylor Swift on "Bad Blood", a song from her fifth album: 2 wds. |
| 37% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 37% | SHEENAEASTON | 12 | "Strut" singer who Prince encouraged and collaborated with in the 1980s: 2 wds. |
| 37% | SHEILAE | 7 | Singer/percussionist who collaborated with Prince on "Purple Rain" (2 wds.) |
| 36% | BILLYIDOL | 9 | 15-Across, 21-Across, and 34-Across singer who turns 65 on November 30 (2 wds.) |
| 36% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 36% | RAVISHANKAR | 11 | Sitar maestro who collaborated with "The Beatles" and who is the father of multiple Grammy-winning singer Norah Jones: 2 wds. |
| 35% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 35% | EMMYLOUHARRIS | 13 | "Blue Kentucky Girl" singer who's one of the three women on the 1987 album "Trio": 2 wds. |
| 35% | DOLLYPARTON | 11 | "9 to 5" singer who's one of the three women on the 1987 album "Trio": 2 wds. |
| 35% | DEBBIEGIBSON | 12 | "Electric Youth" singer who sings "Heartbreak Holiday" with 18-Across and "White Christmas" with her father on 30-Across (2 wds.) |