| 100% | SHEENAEASTON | 12 | "Strut" singer who Prince encouraged and collaborated with in the 1980s: 2 wds. |
| 53% | JANELLEMONAE | 12 | "Dirty Computer" singer and "Glass Onion" actress who Prince encouraged and mentored during collaborations in the 2010s: 2 wds. |
| 52% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 50% | MARYTRAVERS | 11 | Folk singer who, in a trio with Peter and Paul, sang the 1963 hit "Puff, the Magic Dragon": 2 wds. |
| 49% | CARMENELECTRA | 13 | Singer, model, and "Scary Movie" star who Prince encouraged and produced early in her career: 2 wds. |
| 46% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 46% | LUISFONSI | 9 | Singer who hit #1 in 2017 with the Spanish/English-language "Despacito": 2 wds. |
| 46% | RAVISHANKAR | 11 | Sitar maestro who collaborated with "The Beatles" and who is the father of multiple Grammy-winning singer Norah Jones: 2 wds. |
| 46% | REGINABELLE | 11 | "Baby Come to Me" singer who collaborated with 44-Across on the R&B hits "Without You" and 34-Across (2 wds.) |
| 45% | JULIAMICHAELS | 13 | "Issues" singer who's collaborated with Pink, Britney Spears, and Gwen Stefani: 2 wds. |
| 45% | 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% | JIMMIEALLEN | 11 | "Best Shot" singer who collaborated with Brad Paisley on the 2021 country hit "Freedom Was a Highway": 2 wds. |
| 43% | LEEGREENWOOD | 12 | "I.O.U." singer who had a hit in 2001 with "God Bless the U.S.A.": 2 wds. |
| 43% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 43% | 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.) |
| 43% | NICKIMINAJ | 10 | "Anaconda" singer who has lived in both Trinidad and the US: 2 wds. |
| 43% | ALISONKRAUSS | 12 | "When You Say Nothing At All" singer who collaborated with Brad Paisley on the 2004 country hit "Whiskey Lullaby": 2 wds. |
| 43% | DOLLYPARTON | 11 | "Jolene" singer who collaborated with Brad Paisley on the 2005 country hit "When I Get Where I'm Going": 2 wds. |
| 43% | JOHNMELLENCAMP | 14 | "Jack & Diane" singer who had a hit in 1986 with "R.O.C.K. in the U.S.A.": 2 wds. |
| 42% | SELENAGOMEZ | 11 | Actress and singer who voiced Mavis Dracula in the 2012 animated film "Hotel Transylvania": 2 wds. |
| 42% | KATYPERRY | 9 | Singer who collaborated with Snoop Dogg on the 2010 No. 1 Billboard hit "California Gurls" (2 wds.) |
| 41% | BABYARIEL | 9 | TikTok star and singer who appeared in the Disney Channel movie "Zombies 2": 2 wds. |
| 41% | ELTONJOHN | 9 | "Candle in the Wind" singer who said of his upcoming farewell tour, "It's a way of going out with a bang": 2 wds. |
| 41% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 41% | KENNYROGERS | 11 | Country Music Hall of Fame singer who collaborated with 17-Across and 28-Across (2 wds.) |
| 41% | TODDRUNDGREN | 12 | Singer who came up with "Bang the Drum All Day" in his sleep: 2 wds. |
| 41% | SEANKINGSTON | 12 | "Beautiful Girls" singer who has lived in both Jamaica and the US: 2 wds. |
| 41% | NICKJONAS | 9 | "Jealous" pop singer who both hosted and was the musical act in a 2021 "SNL" episode: 2 wds. |
| 41% | FREDDIEMERCURY | 14 | Queen lead singer who shares his name with the smallest planet in the solar system (2 wds.) |
| 41% | 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.) |