| 100% | ADAMLEVINE | 10 | Singer who appears nude in the video of Maroon 5's 2015 single, "This Summer": 2 wds. |
| 65% | BRITNEYSPEARS | 13 | Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds. |
| 65% | MILEYCYRUS | 10 | Singer who appears nude in the video of her 2013 single, "Wrecking Ball": 2 wds. |
| 43% | DONNYOSMOND | 11 | Singer who dances in front of the Schrödinger equation in "Weird Al" Yankovic's "White & Nerdy" video: 2 wds. |
| 41% | SARAHSILVERMAN | 14 | Comedian and "Ralph Breaks the Internet" actress who appeared in Maroon 5's 2018 "Girls Like You" video: 2 wds. |
| 40% | KARLIEKLOSS | 11 | American model and computer programmer who appeared in the music video of "Bad Blood": 2 wds. |
| 40% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 40% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 39% | SINEADOCONNOR | 13 | Irish singer who appeared on the cover of Rolling Stone in its 25th year (1992) (2 wds.) |
| 39% | SNOOPDOGG | 9 | "Gin and Juice" rapper who appears as himself in the 2003 video game "True Crime: Streets of LA": 2 wds. |
| 38% | LORENGRAY | 9 | TikTok star and singer who appeared in the video for Taylor Swift's "The Man": 2 wds. |
| 38% | SMOKEYROBINSON | 14 | "The Tears of a Clown" singer who received the BET Lifetime Achievement Award in 2015: 2 wds. |
| 38% | ELTONJOHN | 9 | "Candle in the Wind" singer/pianist who's the subject of 41-Across: 2 wds. |
| 37% | SHAWNMENDES | 11 | "Señorita" singer who won Canada's Juno Award for Pop Album of the Year in 2019: 2 wds. |
| 37% | TAYLORSWIFT | 11 | "Cardigan" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 37% | LADYGAGA | 8 | "Shallow" pop singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 37% | JASONDERULO | 11 | "Wiggle" R&B singer who's had top 10 hits in each of the last three decades: 2 wds. |
| 37% | BABYARIEL | 9 | TikTok star and singer who appeared in the Disney Channel movie "Zombies 2": 2 wds. |
| 37% | MICHAELKEATON | 13 | "Birdman" actor who appears in the 2015 film "Spotlight": 2 wds. |
| 37% | EARTHAKITT | 10 | "Santa Baby" singer who was the voice of villainous Yzma in Disney's "The Emperor's New Groove": 2 wds. |
| 37% | MARILYNHORNE | 12 | Opera singer who performed at Clinton's 1993 inauguration and received the National Medal of Arts in 1992: 2 wds. |
| 36% | ADAMLEVINE | 10 | Maroon 5 singer who returned as a coach on "The Voice" in 2025 (2 wds.) |
| 36% | DOLLYPARTON | 11 | "Jolene" singer who was MusiCares Person of the Year in 2019: 2 wds. |
| 36% | MICHAELSTIPE | 12 | Singer who came up with "It's the End of the World as We Know It (And I Feel Fine)" in his sleep: 2 wds. |
| 36% | PAULMCCARTNEY | 13 | "Jet" singer who performed in the 2012 London Summer Olympics opening ceremony: 2 wds. |
| 36% | MAVISSTAPLES | 12 | Gospel and soul singer who received the Woody Guthrie Prize in 2015: 2 wds. |
| 36% | NEILDIAMOND | 11 | "Sweet Caroline" singer who was MusiCares Person of the Year in 2009: 2 wds. |
| 35% | KATYPERRY | 9 | "Dark Horse" singer who was the featured act in the 2015 Super Bowl halftime show: 2 wds. |
| 35% | TORIKELLY | 9 | "Nobody Love" singer who first started posting videos on YouTube at the age of 14: 2 wds. |
| 35% | BEVERLYSILLS | 12 | Opera singer who chaired Lincoln Center and received the National Medal of Arts in 1990: 2 wds. |