| 100% | SHAWNMENDES | 11 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 32-Across (2 wds.) |
| 93% | CAMILACABELLO | 13 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 18-Across (2 wds.) |
| 50% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 49% | TAYLORSWIFT | 11 | "Lover" singer who won three 2019 MTV Video Music Awards, including Video of the Year (2 wds.) |
| 49% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 48% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 45% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 43% | 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.) |
| 43% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 42% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 42% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 42% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |
| 42% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 41% | 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.) |
| 40% | TEMPO | 5 | 46-Across song featuring Missy Elliott that was nominated for the 2019 MTV Video Music Award for Best Power Anthem |
| 40% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 39% | WOMANIZER | 9 | 2008 #1 song by 32-Across that won the MTV Video Music Award for Best Pop Video |
| 39% | YOLANDAADAMS | 12 | "Be Blessed" gospel singer who was honored with the 2019 Soul Train Lady of Soul Award: 2 wds. |
| 38% | BEAUTIFULLIAR | 13 | Beyoncé and 36-Across song that won an MTV Video Music Award for Most Earthshattering Collaboration in 2007 (2 wds.) |
| 38% | MISSYELLIOTT | 12 | "Work It" rapper who received the 2019 MTV Video Vanguard Award, the first female rapper to do so: 2 wds. |
| 38% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 38% | DUALIPA | 7 | "Cold Heart" singer who, with Elton John, won the 2022 American Music Award for Collaboration of the Year (2 wds.) |
| 37% | HOTGIRLSUMMER | 13 | Best Power Anthem winner at the 2019 MTV Video Music Awards |
| 37% | SAMSMITH | 8 | "Love Goes" singer who won the GLAAD Media Award for Outstanding Music Artist in 2021: 2 wds. |
| 37% | MARENMORRIS | 11 | "Girl" singer who won the 2019 CMA Award for Album of the Year (2 wds.) |
| 37% | JENNIFERLOPEZ | 13 | "I'm Real" pop singer who received the 2018 MTV Video Vanguard Award, the first Latin artist to do so: 2 wds. |
| 36% | RAMIMALEK | 9 | American actor who won the 2019 Golden Globe Award for Best Actor for the film "Bohemian Rhapsody": 2 wds. |
| 36% | LADYGAGA | 8 | "Born This Way" singer who won the GLAAD Media Award for Outstanding Music Artist in 2012: 2 wds. |
| 36% | JANETJACKSON | 12 | "Rhythm Nation" R&B singer who received the 1990 MTV Video Vanguard Award, the first African American woman to do so: 2 wds. |
| 36% | JUDYWOODRUFF | 12 | "PBS NewsHour" co-anchor who shared the 2017 Walter Cronkite Award for Excellence in Journalism with Gwen Ifill (2 wds.) |