| 100% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 63% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 62% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 61% | 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.) |
| 55% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 54% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 53% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 52% | TIMBERLAKE | 10 | Justin ___, singer who won Video of the Year for "Mirrors" at MTV Video Music Awards in 2013 |
| 52% | KATY | 4 | Singer ___ Perry who won Video of the Year Award for "Firework" at MTV Video Music Awards in 2011 |
| 52% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 51% | TAYLORSWIFT | 11 | "Lover" singer who won three 2019 MTV Video Music Awards, including Video of the Year (2 wds.) |
| 50% | JASONALDEAN | 11 | "You Make It Easy" singer who won Entertainer of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 48% | GAGA | 4 | Lady ___, singer who won the Video of the Year for "Bad Romance" at MTV Video Music Awards in 2011 |
| 47% | DOJACAT | 7 | 13-Across, 19-Across, and 38-Across singer who was named New Artist of the Year at the 2020 American Music Awards (2 wds.) |
| 47% | MIRANDALAMBERT | 14 | "Tin Man" singer who won Female Vocalist of the Year at the 2018 Academy of Country Music Awards: 2 wds. |
| 47% | MIRANDALAMBERT | 14 | "Settling Down" singer who won Entertainer of the Year at the 2022 ACM Awards: 2 wds. |
| 46% | LUKECOMBS | 9 | 15-Across and 33-Across singer who won the 2019 Country Music Association's New Artist of the Year Award (2 wds.) |
| 46% | BTS | 3 | "Dynamite" band who won Best Group, Best K-Pop, and two other awards at the 2020 MTV Video Music Awards |
| 45% | 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.) |
| 45% | MORGANWALLEN | 12 | 15-Across, 38-Across, and "7 Summers" singer who won the iHeartRadio Music Awards Best New Country Artist in 2020 (2 wds.) |
| 45% | ONEDIRECTION | 12 | Boy band that was the Best New Artist at the 2012 MTV Video Music Awards: 2 wds. |
| 44% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 44% | MARENMORRIS | 11 | "The Bones" country singer who won Female Vocalist of the Year at the 2020 CMAs: 2 wds. |
| 44% | SHERYLCROW | 10 | "All I Wanna Do" singer who won the Best New Artist and Record of the Year Grammys in 1995: 2 wds. |
| 44% | NORAHJONES | 10 | "Don't Know Why" singer who won the Best New Artist and Record of the Year Grammys in 2003: 2 wds. |
| 44% | BLACKPINK | 9 | "How You Like That" band who won Song of Summer at the 2020 MTV Video Music Awards |
| 44% | AUSTINMAHONE | 12 | YouTube sensation who was the Artist to Watch at the 2013 MTV Video Music Awards: 2 wds. |
| 43% | COLDPLAY | 8 | "Orphans" band who won Best Rock at the 2020 MTV Video Music Awards |
| 43% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 43% | 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 |