| 100% | GLORIAESTEFAN | 13 | "Coming Out of the Dark" singer who, with her husband Emilio, won the 2019 Gershwin Prize: 2 wds. |
| 62% | GLORIAESTEFAN | 13 | Miami Sound Machine singer/songwriter honored with her husband Emilio with the 2019 Gershwin Prize for Popular Song (2 wds.) |
| 51% | GLORIAESTEFAN | 13 | "Coming Out of the Dark" singer who's part owner of the Miami Dolphins: 2 wds. |
| 51% | ARIANAGRANDE | 12 | Singer who spells out the title of her 2019 hit "NASA": 2 wds. |
| 48% | GLORIAESTEFAN | 13 | Cuban-American singer with the 1991 #1 hit "Coming Out of the Dark": 2 wds. |
| 47% | TONYBENNETT | 11 | "Rags to Riches" singer who won the 2017 Library of Congress Gershwin Prize for Popular Song: 2 wds. |
| 44% | ARETHAFRANKLIN | 14 | Singer who spells out the title of her 1967 hit "Respect": 2 wds. |
| 44% | MICHELLEBRANCH | 14 | The Wreckers singer who appeared on "The Big Interview with Dan Rather" with her husband, Patrick Carney of the Black Keys (2 wds.) |
| 43% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 42% | GARTHBROOKS | 11 | "Friends in Low Places" singer who won the 2020 Gershwin Prize: 2 wds. |
| 42% | QUEENLATIFAH | 12 | Singer who spells out the title of her 1994 hit "U.N.I.T.Y.": 2 wds. |
| 41% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 41% | YOLANDAADAMS | 12 | "Be Blessed" gospel singer who was honored with the 2019 Soul Train Lady of Soul Award: 2 wds. |
| 41% | KANDIBURRUSS | 12 | R&B singer with Xscape who won season 3 of "The Masked Singer" as the Night Angel: 2 wds. |
| 41% | GEORGEFOREMAN | 13 | "Rumble in the Jungle" boxer who came out of retirement in 1987 and later won the heavyweight title: 2 wds. |
| 40% | 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. |
| 40% | ALISTROKER | 10 | Actress who won a Tony for her role as Ado Annie in the 2019 Broadway revival of "Oklahoma!": 2 wds. |
| 40% | SAMSMITH | 8 | "Stay With Me" singer who was a first-time Grammy nominee for Record of the Year (and won): 2 wds. |
| 40% | KELLIEPICKLER | 13 | "Best Days of Your Life" singer who won Season 16 of "Dancing With the Stars" (2 wds.) |
| 39% | ALISONKRAUSS | 12 | Singer who won her 27th Grammy for the 2011 bluegrass album "Paper Airplane": 2 wds. |
| 39% | 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. |
| 39% | MARENMORRIS | 11 | Her "Girl" won the 2019 CMA for Album of the Year: 2 wds. |
| 39% | KELLIEPICKLER | 13 | "Best Days of Your Life" singer who won "Dancing with the Stars" season 16 (2 wds.) |
| 39% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 39% | DICKSARGENT | 11 | "Bewitched" actor who came out of the closet in 1991 at age 61: 2 wds. |
| 39% | ASHLEYMCBRYDE | 13 | "Girl Going Nowhere" singer who won the 2019 CMA Award for New Artist of the Year (2 wds.) |
| 39% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 38% | GEORGETAKEI | 11 | "Star Trek" actor who came out of the closet in 2005 at age 68: 2 wds. |
| 38% | KELLYCLARKSON | 13 | Female singer who won the inaugural season of "American Idol": 2 wds. |
| 38% | TAYLORSWIFT | 11 | "Lover" singer who won three 2019 MTV Video Music Awards, including Video of the Year (2 wds.) |