| 100% | JONIMITCHELL | 12 | "Help Me" singer/songwriter who has nine Grammys: 2 wds. |
| 53% | STEVIEWONDER | 12 | "Superstition" singer who has won 25 Grammys: 2 wds. |
| 53% | JOHNLEGEND | 10 | "All of Me" singer who has his own wine label, LVE: 2 wds. |
| 52% | DAVEMATTHEWS | 12 | "Crash Into Me" singer who has his own wine label, Dreaming Tree Wines: 2 wds. |
| 51% | MARYJBLIGE | 10 | 13-Across and 44-Across singer/songwriter who has won a total of nine Grammys in four categories, Gospel, Pop, R&B, and Rap (3 wds.) |
| 48% | TAYLORSWIFT | 11 | American singer who has made hits like "You Belong With Me," and is currently dating British actor Joe Alwyn: 2 wds. |
| 48% | TAYLORSWIFT | 11 | Singer of "Me!" who has 134 million Instagram followers: 2 wds. |
| 47% | BILLIEEILISH | 12 | Singer-songwriter who sings "What Was I Made For?" on "Barbie: The Album" (2 wds.) |
| 47% | MARIAHCAREY | 11 | Singer who has had 19 #1 hits, including "Emotions": 2 wds. |
| 46% | SELENAGOMEZ | 11 | Singer of "Lose You to Love Me" who has 179 million Instagram followers: 2 wds. |
| 46% | TAYLORSWIFT | 11 | Singer who has had 12 #1 hits, including "Blank Space": 2 wds. |
| 46% | HARRYCONNICKJR | 14 | Singer/songwriter born September 11 who has had nine #1 albums on Billboard's Jazz Albums chart (3 wds.) |
| 46% | 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. |
| 45% | RODSTEWART | 10 | British singer/songwriter who had a Top 20 hit with his version of "Forever Young" in 1988 (2 wds.) |
| 45% | ARIANAGRANDE | 12 | American singer/songwriter who sings "Rain on Me" with Lady Gaga on "Chromatica" (2 wds.) |
| 44% | JACKWAGNER | 10 | "General Hospital" star who had a top 10 hit with "All I Need" in 1984: 2 wds. |
| 44% | MARIAHCAREY | 11 | "We Belong Together" singer who has Venezuelan roots: 2 wds. |
| 44% | NORAHJONES | 10 | "Don't Know Why" singer who has won nine Grammy Awards (2 wds.) |
| 43% | SELENAGOMEZ | 11 | "Come & Get It" singer who has Mexican roots: 2 wds. |
| 43% | MAXSCHERZER | 11 | Cy Young-winning Nationals pitcher who has recorded two "immaculate" innings (three strikeouts on nine total pitches): 2 wds. |
| 43% | MANN | 4 | Singer Aimee who has two Grammys |
| 43% | SINEADOCONNOR | 13 | Irish singer who had the #1 hit "Nothing Compares 2 U": 2 wds. |
| 43% | CHARLIEPUTH | 11 | "Attention" singer who has a song named after Marvin Gaye: 2 wds. |
| 43% | LIAMPAYNE | 9 | One Direction singer who has a fear of spoons: 2 wds. |
| 43% | ALISONKRAUSS | 12 | "When You Say Nothing at All" country singer who has won 27 Grammys: 2 wds. |
| 42% | NICKIMINAJ | 10 | "Anaconda" singer who has lived in both Trinidad and the US: 2 wds. |
| 42% | JOHNWILLIAMS | 12 | "Jaws" and "Star Wars" composer who has won 26 Grammys: 2 wds. |
| 42% | GARTHBROOKS | 11 | Country singer who has not made his music available on Spotify or iTunes: 2 wds. |
| 42% | ARIANAGRANDE | 12 | Singer of "7 Rings" who has 189 million Instagram followers: 2 wds. |
| 42% | GERIHALLIWELL | 13 | Singer who had four #1 hits in the UK from 1999 to 2001, including "It's Raining Men": 2 wds. |