| 100% | TORIKELLY | 9 | "Nobody Love" singer who first started posting videos on YouTube at the age of 14: 2 wds. |
| 40% | MIRANDALAMBERT | 14 | "Vice" singer who came in third on the first season of "Nashville Star": 2 wds. |
| 39% | MILEYCYRUS | 10 | Singer who won Video of the Year for "Wrecking Ball" at MTV Video Music Awards in 2014: 2 wds. |
| 39% | BRITNEYSPEARS | 13 | Singer who won Video of the Year for "Piece of Me" at MTV Video Music Awards in 2008: 2 wds. |
| 37% | KELLYCLARKSON | 13 | "Before Your Love" singer who was the first winner of 40-Across (2 wds.) |
| 36% | THEWEEKND | 9 | Stage name of "Starboy" singer who used the name for anonymity on YouTube: 2 wds. |
| 36% | 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.) |
| 36% | JOHNKEATS | 9 | Romantic poet who died at the age of 25, but left a lasting impression on the literary world through his odes like "To Autumn": 2 wds. |
| 36% | MIRANDALAMBERT | 14 | "Bluebird" country singer who won Music Video of the Year at the 2020 CMAs: 2 wds. |
| 36% | BRITNEYSPEARS | 13 | Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds. |
| 35% | WILLIENELSON | 12 | "Always on My Mind" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 35% | ADAMLEVINE | 10 | Singer who appears nude in the video of Maroon 5's 2015 single, "This Summer": 2 wds. |
| 35% | MILEYCYRUS | 10 | Singer who appears nude in the video of her 2013 single, "Wrecking Ball": 2 wds. |
| 35% | ZAYNMALIK | 9 | One Direction singer who changed the spelling of his first name: 2 wds. |
| 35% | MILEYCYRUS | 10 | "Wrecking Ball" singer who performs on the remix of 49-Across: 2 wds. |
| 35% | THEWEEKND | 9 | "Blinding Lights" singer who won Video of the Year and Best R&B at the 2020 MTV Video Music Awards (2 wds.) |
| 35% | HARRYBELAFONTE | 14 | "Day-O" singer/actor/activist who passed away on April 25, 2023, at the age of 96 (2 wds.) |
| 35% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 35% | JAMESBROWN | 10 | Rock singer who was the subject of the 2014 biopic "Get On Up": 2 wds. |
| 35% | MARYSHELLEY | 11 | Author who began writing 28-Across at the age of 18: 2 wds. |
| 34% | PATTILABELLE | 12 | "New Attitude" singer who was the Flower on season 2 of "The Masked Singer": 2 wds. |
| 34% | KACEYMUSGRAVES | 14 | "Follow Your Arrow" singer who finished seventh on the fifth season of "Nashville Star": 2 wds. |
| 34% | ARIANAGRANDE | 12 | "Thank U Next" singer who sings "Met Him Last Night" with Demi Lovato on "Dancing with the Devil ... the Art of Starting Over" (2 wds.) |
| 34% | DONNYOSMOND | 11 | Singer who dances in front of the Schrödinger equation in "Weird Al" Yankovic's "White & Nerdy" video: 2 wds. |
| 34% | JIMMORRISON | 11 | Frontman of "The Doors" who died at the age of 27: 2 wds. |
| 34% | GLADYSKNIGHT | 12 | "Midnight Train to Georgia" singer who was the Bee on season 1 of "The Masked Singer": 2 wds. |
| 34% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 34% | SAMFISCHER | 10 | "This City" singer who sings "What Other People Say" with Demi Lovato on the 2021 album "Dancing with the Devil ... the Art of Starting Over" (2 wds.) |
| 33% | THOMASRHETT | 11 | "Country Again" singer who won Entertainer of the Year at the 2020 Academy of Country Music Awards: 2 wds. |
| 33% | ASHLEIGHBARTY | 13 | #1 tennis player who retired in 2022 at the age of 25: 2 wds. |