| 100% | BRITNEYSPEARS | 13 | Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds. |
| 84% | MILEYCYRUS | 10 | Singer who appears nude in the video of her 2013 single, "Wrecking Ball": 2 wds. |
| 75% | ADAMLEVINE | 10 | Singer who appears nude in the video of Maroon 5's 2015 single, "This Summer": 2 wds. |
| 53% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 48% | LORENGRAY | 9 | TikTok star and singer who appeared in the video for Taylor Swift's "The Man": 2 wds. |
| 47% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 47% | DONNYOSMOND | 11 | Singer who dances in front of the Schrödinger equation in "Weird Al" Yankovic's "White & Nerdy" video: 2 wds. |
| 46% | AMYWINEHOUSE | 12 | "Rehab" singer who won the Best New Artist and Record of the Year Grammys in 2008: 2 wds. |
| 46% | SNOOPDOGG | 9 | "Gin and Juice" rapper who appears as himself in the 2003 video game "True Crime: Streets of LA": 2 wds. |
| 45% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 43% | CELINEDION | 10 | "The Power of Love" singer who was made a Companion of the Order of Canada in 2008: 2 wds. |
| 43% | KARLIEKLOSS | 11 | American model and computer programmer who appeared in the music video of "Bad Blood": 2 wds. |
| 43% | BABYARIEL | 9 | TikTok star and singer who appeared in the Disney Channel movie "Zombies 2": 2 wds. |
| 42% | JENNIFERLOPEZ | 13 | "I'm Real" singer who became a mother of twins in 2008: 2 wds. |
| 42% | WARRENSAPP | 10 | Former NFL player who appeared on "Dancing With the Stars" in 2008: 2 wds. |
| 42% | NEILDIAMOND | 11 | "Sweet Caroline" singer who was MusiCares Person of the Year in 2009: 2 wds. |
| 42% | JANETJACKSON | 12 | "Rhythm Nation" singer who received the GLAAD Vanguard Award in 2008: 2 wds. |
| 42% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 42% | MICHELLEBRANCH | 14 | The Wreckers singer who appeared on "The Big Interview with Dan Rather" with her husband, Patrick Carney of the Black Keys (2 wds.) |
| 41% | ELLENDEGENERES | 14 | Comedian and daytime talk host who appeared in the "Girls Like You" video: 2 wds. |
| 41% | TIFFANYHADDISH | 14 | Comedian and "Girls Trip" actress who appeared in the "Girls Like You" video: 2 wds. |
| 41% | ELTONJOHN | 9 | "Candle in the Wind" singer/pianist who's the subject of 41-Across: 2 wds. |
| 41% | ALESSIACARA | 11 | "Stay" singer who won the Pop Album of the Year Juno in 2017: 2 wds. |
| 41% | RICKYMARTIN | 11 | "Livin' la Vida Loca" singer who became a father of twins in 2008: 2 wds. |
| 41% | JONIMITCHELL | 12 | "Both Sides Now" singer who was MusiCares Person of the Year in 2022: 2 wds. |
| 41% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 41% | GARYCOLEMAN | 11 | "Diff'rent Strokes" star who appears as himself in the 2003 video game "Postal 2": wds. |
| 41% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 41% | TORIKELLY | 9 | "Nobody Love" singer who first started posting videos on YouTube at the age of 14: 2 wds. |
| 41% | BEVERLYSILLS | 12 | Opera singer who chaired Lincoln Center and received the National Medal of Arts in 1990: 2 wds. |