| 100% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 61% | ROBERT | 6 | With 31-Across, singer who performed his song "Addicted to Love" to open the third MTV Video Music Awards, in 1986 |
| 52% | EURYTHMICS | 10 | Duo who performed their song "Would I Lie to You?" to open the second MTV Video Music Awards, in 1985 |
| 47% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 46% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 45% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 43% | JENNIFERLOPEZ | 13 | "I'm Real" pop singer who received the 2018 MTV Video Vanguard Award, the first Latin artist to do so: 2 wds. |
| 43% | 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. |
| 43% | JUSTINBIEBER | 12 | Singer whose "Peaches" won the MTV Video Music Award for Best Pop Video in 2021: 2 wds. |
| 42% | TAYLORSWIFT | 11 | Singer whose "Anti-Hero" won the MTV Video Music Award for Best Pop Video in 2023: 2 wds. |
| 41% | HARRYSTYLES | 11 | Singer whose "As It Was" won the MTV Video Music Award for Best Pop Video in 2022: 2 wds. |
| 41% | PAULMCCARTNEY | 13 | "Jet" singer who performed in the 2012 London Summer Olympics opening ceremony: 2 wds. |
| 41% | BRYANADAMS | 10 | "Heaven" singer who performed in the 2010 Vancouver Winter Olympics opening ceremony: 2 wds. |
| 41% | CAMILACABELLO | 13 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 18-Across (2 wds.) |
| 41% | SHAWNMENDES | 11 | "Señorita" singer who shared the 2019 MTV Video Music Award for Best Collaboration with 32-Across (2 wds.) |
| 41% | AUSTINMAHONE | 12 | YouTube sensation who was the Artist to Watch at the 2013 MTV Video Music Awards: 2 wds. |
| 40% | LEANNRIMES | 10 | "Blue" singer who performed in the 2002 Salt Lake City Winter Olympics opening ceremony: 2 wds. |
| 40% | SOLANGEKNOWLES | 14 | 12-Across and 28-Across singer who was the first recipient of the "Billboard" Women in Music Impact Award (2 wds.) |
| 40% | MISSYELLIOTT | 12 | "Work It" rapper who received the 2019 MTV Video Vanguard Award, the first female rapper to do so: 2 wds. |
| 39% | TAYLORSWIFT | 11 | "Lover" singer who won three 2019 MTV Video Music Awards, including Video of the Year (2 wds.) |
| 39% | BONNIERAITT | 11 | "Something to Talk About" singer who received the Billboard Women in Music Icon Award in 2021: 2 wds. |
| 38% | DEBBIEHARRY | 11 | Lead singer of Blondie who received the first Billboard Women in Music Icon Award, in 2008: 2 wds. |
| 38% | MARIAHCAREY | 11 | "Fantasy" singer who recently became the first person to top the Billboard Hot 100 in four different decades: 2 wds. |
| 38% | ISAACHAYES | 10 | "Soul Man" singer who won an Academy Award for Best Original Song for his work on the film "Shaft": 2 wds. |
| 38% | BRUNOMARS | 9 | "24K Magic" singer who won the award for R&B Song, "That's What I Like" in Billboard 2018: 2 wds |
| 37% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 36% | SEBASTIANYATRA | 14 | "Dos Oruguitas" singer who won the 2022 American Music Award for Favorite Latin Song (2 wds.) |
| 36% | CYNDILAUPER | 11 | "Girls Just Want to Have Fun" singer who received the Billboard Women in Music Icon Award in 2018: 2 wds. |
| 36% | CHARLEYPRIDE | 12 | "Kiss an Angel Good Mornin'" singer who was the first Black country artist to cohost the CMA Awards (1975) and the ACM Awards (1980): 2 wds. |
| 36% | KYLIEMINOGUE | 12 | "Padam Padam" singer who received the Billboard Women in Music Icon Award in 2024: 2 wds. |