| 100% | DIONNEWARWICK | 13 | "Walk On By" singer who married the same man twice: 2 wds. |
| 70% | JUDYSHEINDLIN | 13 | TV judge who married the same man twice: 2 wds. |
| 55% | DIONNEWARWICK | 13 | "Walk On By" singer who was the Mouse on season 3 of "The Masked Singer": 2 wds. |
| 51% | DIONNEWARWICK | 13 | "Walk On By" singer who has a solo in "We Are the World": 2 wds. |
| 49% | RICHARDBURTON | 13 | "Who's Afraid of Virginia Woolf?" actor who married the same woman twice: 2 wds. |
| 48% | STEPHENSTILLS | 13 | American singer and songwriter who is the first artist to be inducted twice on the same night into the Rock and Roll Hall of Fame: 2 wds. |
| 46% | DIONNEWARWICK | 13 | "Walk on By" singer honored by the Kennedy Center in 2023 (2 wds.) |
| 46% | BRUNOMARS | 9 | Singer who did the vocals on "Uptown Funk": 2 wds. |
| 46% | TAMMYWYNETTE | 12 | "Stand by Your Man" singer who received the Grammy Lifetime Achievement Award in 2024: 2 wds. |
| 46% | BOBBYRYDELL | 11 | "Volare" singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 45% | BILLYJOEL | 9 | "Piano Man" singer who once boxed on the Golden Gloves circuit: 2 wds. |
| 45% | JUSTINBIEBER | 12 | "Yummy" singer who was half the duet on 27-Across: 2 wds. |
| 45% | ISAACHAYES | 10 | "Soul Man" singer who won an Academy Award for Best Original Song for his work on the film "Shaft": 2 wds. |
| 45% | ELVISCOSTELLO | 13 | "Veronica" new wave singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 45% | TANYATUCKER | 11 | "Delta Dawn" country singer who was honored with a star on the Hollywood Walk of Fame in 2020 (2 wds.) |
| 45% | EDSHEERAN | 9 | Singer who collaborated with Beyoncé on the 2017 #1 hit "Perfect Duet": 2 wds. |
| 44% | MILEYCYRUS | 10 | "Wrecking Ball" singer who performs on the remix of 49-Across: 2 wds. |
| 44% | BRUNOMARS | 9 | "Grenade" singer who was the featured vocalist on "Uptown Funk": 2 wds. |
| 44% | DAVIDBOWIE | 10 | Singer who featured the glam rocker character Ziggy Stardust on his 1972 concept album: 2 wds. |
| 44% | KATYPERRY | 9 | "Roar" singer who's #11 on the 2013 Maxim Hot 100 List: 2 wds. |
| 44% | ARIANAGRANDE | 12 | "7 Rings" singer who was half the duet on 27-/31-Across: 2 wds. |
| 43% | JANELLEMONAE | 12 | Singer who featured the android character Cindi Mayweather on her 2010 "The ArchAndroid" concept album: 2 wds. |
| 43% | CAMILACABELLO | 13 | Singer who collaborated with Machine Gun Kelly in 2017 on the #4 hit "Bad Things": 2 wds. |
| 43% | MIRANDALAMBERT | 14 | "Vice" singer who came in third on the first season of "Nashville Star": 2 wds. |
| 43% | TOBYKEITH | 9 | Singer who duetted with Willie Nelson on the 2003 #1 country hit "Beer for My Horses": 2 wds. |
| 43% | KACEYMUSGRAVES | 14 | "Follow Your Arrow" singer who finished seventh on the fifth season of "Nashville Star": 2 wds. |
| 43% | STEVIEWONDER | 12 | "Sir Duke" singer who debuted songs on the Hot 100 in five different decades: 2 wds. |
| 42% | ANDRADAY | 8 | Singer who performed "Stand Up for Something" at the 2018 Oscars, accompanied by Common and various activists: 2 wds. |
| 42% | LORENGRAY | 9 | TikTok star and singer who appeared in the video for Taylor Swift's "The Man": 2 wds. |
| 42% | KELLYCLARKSON | 13 | "Piece by Piece" singer who performed "It's Quiet Uptown" on "The Hamilton Mixtape": 2 wds. |