| 100% | TONYBENNETT | 11 | "Rags to Riches" singer who won the 2017 Library of Congress Gershwin Prize for Popular Song: 2 wds. |
| 46% | STEVIEWONDER | 12 | Singer who won the Oscar for Best Original Song, "Just Called to Say I Love You": 2 wds. |
| 43% | GARTHBROOKS | 11 | "Ask Me How I Know" singer who won the 2017 CMA Award for Entertainer of the Year (2 wds.) |
| 42% | TAYLORSWIFT | 11 | "Better Man" songwriter who won the 2017 CMA Award for Song of the Year (2 wds.) |
| 41% | CHRISSTAPLETON | 14 | "From a Room: Volume 1" singer who won the 2017 CMA Awards for Male Vocalist of the Year and Album of the Year (2 wds.) |
| 41% | TONYBENNETT | 11 | "I Left My Heart in San Francisco" singer honored with the 2017 Gershwin Prize for Popular Song (2 wds.) |
| 41% | GARTHBROOKS | 11 | "Friends in Low Places" singer who won the 2020 Gershwin Prize: 2 wds. |
| 41% | STEVIEWONDER | 12 | "Superstition" singer/songwriter honored with the 2009 Gershwin Prize for Popular Song (2 wds.) |
| 40% | LIONELRICHIE | 12 | Singer who won the Oscar in 1986 for Best Original Song, "Say You, Say Me": 2 wds. |
| 40% | HARRYSTYLES | 11 | "As It Was" singer who won the People's Choice Award for Male Artist of 2022: 2 wds. |
| 40% | ALANJACKSON | 11 | "Country Boy" singer who won the CMA Award for Entertainer of the Year three times: 2 wds. |
| 40% | KENNYCHESNEY | 12 | "Come Over" singer who won the CMA Award for Entertainer of the Year four times: 2 wds. |
| 40% | TAYLORSWIFT | 11 | "Lavender Haze" singer who won the People's Choice Award for Female Artist of 2022: 2 wds. |
| 39% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 39% | KAZUOISHIGURO | 13 | Author who won the Booker Prize for "The Remains of the Day": 2 wds. |
| 39% | GARTHBROOKS | 11 | "The River" singer who won the CMA Award for Entertainer of the Year seven times: 2 wds. |
| 39% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |
| 39% | DWAYNEJOHNSON | 13 | "Hobbs & Shaw" actor who won the NAACP Image Award for Entertainer of the Year in 2017: 2 wds. |
| 39% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 39% | SMOKEYROBINSON | 14 | "Being with You" singer/songwriter honored with the 2016 Gershwin Prize for Popular Song (2 wds.) |
| 39% | JULIANBARNES | 12 | English author who won the Man Booker Prize for "The Sense of an Ending": 2 wds. |
| 39% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 39% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 39% | GLORIAESTEFAN | 13 | "Coming Out of the Dark" singer who, with her husband Emilio, won the 2019 Gershwin Prize: 2 wds. |
| 39% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 38% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 38% | GARTHBROOKS | 11 | "Friends in Low Places" singer/songwriter honored with the 2020 Gershwin Prize for Popular Song (2 wds.) |
| 38% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 38% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 38% | ASHLEYMCBRYDE | 13 | "Girl Going Nowhere" singer who won the 2019 CMA Award for New Artist of the Year (2 wds.) |