| 100% | ADELE | 5 | One-named singer who won the 2016 Album of the Year |
| 78% | JUSTIN | 6 | With 35-Across, "Yummy" singer who won the Pop Album of the Year Juno in 2011 and 2016 |
| 71% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 64% | GARTHBROOKS | 11 | "The Dance" singer who won the 2016 CMA Award for Entertainer of the Year: 2 wds. |
| 64% | MARENMORRIS | 11 | "My Church" singer who won the 2016 CMA New Artist of the Year award: 2 wds. |
| 63% | LITTLEBIGTOWN | 13 | "Girl Crush" singers who won the 2016 CMA Award for Vocal Group of the Year: 3 wds. |
| 63% | TAYLORSWIFT | 11 | Singer-songwriter whose "1989" won 2016's Grammy Award for Album of the Year (2 wds.) |
| 62% | ADELE | 5 | British singer who won the Album of the Year Grammy in 2012 for "21" |
| 62% | BECK | 4 | Artist who won the 2014 Album of the Year Grammy |
| 62% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 61% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 60% | BOB | 3 | ___ Dylan, American singer who won a Grammy for Album of the Year in 1973 |
| 60% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 59% | BURTONCUMMINGS | 14 | Singer-songwriter in the Canadian Music Hall of Fame who won the 1979 Album of the Year Juno Award for "Dream of a Child" (2 wds.) |
| 59% | LEONARDCOHEN | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2017 Album of the Year Juno Award for "You Want It Darker" (2 wds.) |
| 59% | MARS | 4 | Singer Bruno who won Grammys for Record, Album, and Song of the Year in 2018 |
| 58% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 57% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 57% | 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.) |
| 57% | ANDRE | 5 | ___ Blake, Jamaican soccer player who won the MLS Goalkeeper of the Year Award in 2016 and 2020 |
| 55% | ZAYNMALIK | 9 | One Direction singer who changed the spelling of his first name: 2 wds. |
| 55% | STEVIEWONDER | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Innervisions": 2 wds. |
| 55% | ZAYN | 4 | "Pillowtalk" singer who won the Billboard Music Award for New Artist of the Year as a member of One Direction in 2013 and as a solo artist in 2017 |
| 55% | KACEYMUSGRAVES | 14 | 19-Across and 46-Across singer who won four 2019 Grammys, including Album of the Year and Best Country Album for "Golden Hour" (2 wds.) |
| 54% | JOHNHANES | 9 | American engineer/mixer who has won the Grammy thrice for "Best Album of the Year," including one for "24k Magic": 2 wds. |
| 54% | JONIMITCHELL | 12 | Singer-songwriter in the Canadian Music Hall of Fame who won the 2001 Vocal Jazz Album of the Year Juno Award for "Both Sides Now" (2 wds.) |
| 54% | FRANKSINATRA | 12 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "September of My Years": 2 wds. |
| 54% | PAULSIMON | 9 | American artist who has won the Grammy thrice for "Best Album of the Year," including one for "Bridge over Troubled Water": 2 wds. |
| 54% | JENNIFERLOPEZ | 13 | "Let's Get Loud" singer who was named Glamour Woman of the Year in 1999 and 2011: 2 wds. |
| 53% | GARTHBROOKS | 11 | "The Dance" country singer who won the 2019 CMA for Entertainer of the Year: 2 wds. |