| 100% | GAGA | 4 | Lady ___, singer who won the Video of the Year for "Bad Romance" at MTV Video Music Awards in 2011 |
| 77% | KATY | 4 | Singer ___ Perry who won Video of the Year Award for "Firework" at MTV Video Music Awards in 2011 |
| 70% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 70% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 67% | TIMBERLAKE | 10 | Justin ___, singer who won Video of the Year for "Mirrors" at MTV Video Music Awards in 2013 |
| 56% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 55% | LADYGAGA | 8 | "Rain on Me" singer who won the MTV Tricon Award, Artist of the Year, and two other awards at the 2020 MTV Video Music Awards (2 wds.) |
| 54% | RAIN | 4 | "___ On Me," song by Lady Gaga and Ariana Grande that won the MTV Video Music Award for Song of the Year in 2020 |
| 51% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 51% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 51% | TAYLORSWIFT | 11 | "Lover" singer who won three 2019 MTV Video Music Awards, including Video of the Year (2 wds.) |
| 49% | 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.) |
| 49% | 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.) |
| 49% | 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 |
| 49% | 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.) |
| 48% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 48% | CHRISSTAPLETON | 14 | "Tennessee Whiskey" singer-songwriter who won Male Vocalist of the Year at the 2023 Country Music Association Awards (2 wds.) |
| 47% | LUNCH | 5 | Billie Eilish hit nominated for Video of the Year at the 2024 MTV Video Music Awards |
| 47% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 47% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 47% | RAFAEL | 6 | ___ Nadal, tennis player who won the Laureus World Sports Award for Sportsman of the Year in 2011 |
| 47% | ADELE | 5 | British singer who won the Album of the Year Grammy in 2012 for "21" |
| 47% | BILLIEEILISH | 12 | "All the Good Girls Go to Hell" singer who won the 2019 American Music Award for New Artist of the Year (2 wds.) |
| 46% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 46% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 46% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 45% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 45% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 45% | SLEDGEHAMMER | 12 | Song that accounted for 9 of the 10 MTV Video Music Awards won by 17-Across in 1987 |
| 45% | BLOOD | 5 | "Bad ___," song by Taylor Swift that won an MTV VMA for Video of the Year in 2015 |