| 100% | 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.) |
| 81% | 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.) |
| 73% | 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.) |
| 51% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 49% | GARTHBROOKS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Male Country Artist a record eight times (2 wds.) |
| 49% | REBAMCENTIRE | 12 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Female Country Artist a record 11 times (2 wds.) |
| 48% | KENNYROGERS | 11 | Country Music Hall of Fame singer who's won the American Music Award for Favorite Country Single a record five times (2 wds.) |
| 48% | CONWAYTWITTY | 12 | Country Music Hall of Fame singer who shared four consecutive CMA Awards for Vocal Duo of the Year with 28-Across in the 1970s (2 wds.) |
| 48% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 46% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 46% | DAWNSTALEY | 10 | Basketball Hall of Fame inductee who won four Coach of the Year awards in 2020: 2 wds. |
| 46% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 43% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 43% | 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.) |
| 42% | ANNIELENNOX | 11 | "Sweet Dreams (Are Made of This)" singer who was voted into the Songwriters Hall of Fame in 2020: 2 wds. |
| 42% | TAYLORSWIFT | 11 | "Anti-Hero" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 42% | HARRYSTYLES | 11 | "As It Was" singer who is nominated for a 2022 American Music Award for Artist of the Year (2 wds.) |
| 41% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 41% | 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 |
| 41% | DOLLYPARTON | 11 | "Jolene" singer who was inducted into the Country Music Hall of Fame in 1999: 2 wds. |
| 41% | YOLANDAADAMS | 12 | "Already Alright" singer who was inducted into the Gospel Music Hall of Fame in 2017: 2 wds. |
| 41% | CARLYPEARCE | 11 | "I Hope You're Happy Now" singer/songwriter who won the 2021 Country Music Association Award for Female Vocalist of the Year (2 wds.) |
| 41% | ELVISPRESLEY | 12 | "Love Me Tender" singer who was inducted into the Gospel Music Hall of Fame in 2001: 2 wds. |
| 40% | GARTHBROOKS | 11 | "That Girl Is a Cowboy" singer who won the 2019 CMA Award for Entertainer of the Year (2 wds.) |
| 40% | ANDRAECROUCH | 12 | "Soon and Very Soon" singer who was inducted into the Gospel Music Hall of Fame in 1998: 2 wds. |
| 40% | LORETTALYNN | 11 | "Coal Miner's Daughter" singer who was inducted into the Country Music Hall of Fame in 1988: 2 wds. |
| 40% | HARLANHOWARD | 12 | Songwriter in the Nashville Songwriters, Country Music, and Songwriters Halls of Fame who wrote the songs on 40-Across's 2023 album (2 wds.) |
| 40% | DANFOUTS | 8 | San Diego Chargers quarterback who never won a Super Bowl but is in the Pro Football Hall of Fame: 2 wds. |
| 40% | RASCALFLATTS | 12 | "Yours If You Want It" singers who have won the Country Music Association Award for Vocal Group of the Year six times (2 wds.) |
| 40% | TAMMYWYNETTE | 12 | "D-I-V-O-R-C-E" singer who was inducted into the Country Music Hall of Fame in 1998: 2 wds. |