| 100% | COREYHART | 9 | Canadian-born singer who released "Sunglasses at Night" in 1984: 2 wds. |
| 63% | JUSTINBIEBER | 12 | Canadian-born singer who released "Boyfriend" in 2012: 2 wds. |
| 62% | AVRILLAVIGNE | 12 | Canadian-born singer who released "Sk8er Boi" in 2002: 2 wds. |
| 61% | NEILYOUNG | 9 | Canadian-born singer who released "Rockin' in the Free World" in 1989: 2 wds. |
| 54% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 53% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 51% | NELLYFURTADO | 12 | Singer who released "I'm Like a Bird" in 2000: 2 wds. |
| 51% | BILLIEEILISH | 12 | Singer who released "Birds of a Feather" in 2024: 2 wds. |
| 49% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 47% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 44% | BILLYPRESTON | 12 | Singer who sang with Nat King Cole on a TV show at 11 and released his first album at 16: 2 wds. |
| 43% | LEONARDCOHEN | 12 | Canadian singer/songwriter who wrote and recorded 34-Across in 1984 (2 wds.) |
| 43% | PETERGABRIEL | 12 | "Big Time" singer who won 10 MTV Video Music Awards in 1987, the most wins ever in a single night: 2 wds. |
| 42% | LADYGAGA | 8 | 15-Across, 9-Down, and 22-Down singer who released the studio album "Mayhem" in 2025 (2 wds.) |
| 42% | DUALIPA | 7 | "Dance the Night" singer who played Mermaid Barbie in "Barbie": 2 wds. |
| 42% | GEORGESTRAIT | 12 | 18-Across and 29-Across singer who released his 30th studio album, "Honky Tonk Time Machine," in 2019 (2 wds.) |
| 41% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who was born and raised in Hawaii: 2 wds. |
| 41% | LENAHORNE | 9 | Singer who played Glinda the Good Witch in "The Wiz": 2 wds. |
| 41% | FIONAAPPLE | 10 | 18-Across, 25-Across, and 38-Across singer who released her fifth studio album "Fetch the Boltcutters" in 2020 (2 wds.) |
| 41% | MEGHANTRAINOR | 13 | 18-Across, 40-Across, and "All About That Bass" singer who released her sixth studio album, "Timeless," in 2024 (2 wds.) |
| 41% | AMBERRILEY | 10 | Singer who played Addaperle in "The Wiz Live!": 2 wds. |
| 41% | QUEENLATIFAH | 12 | Singer who played the Wiz in "The Wiz Live!": 2 wds. |
| 41% | DIANAROSS | 9 | Singer who played Dorothy in 1978's "The Wiz": 2 wds. |
| 40% | ELTONJOHN | 9 | "Rocket Man" singer who hosted and performed on "Saturday Night Live" in 2011: 2 wds. |
| 40% | JACKWHITE | 9 | "Lazaretto" rock singer who headlined at the 2015 Coachella Festival: 2 wds. |
| 40% | BADBUNNY | 8 | Puerto Rican singer who acted in the film "Bullet Train": 2 wds. |
| 40% | ELVISCOSTELLO | 13 | "Veronica" singer who was born Declan Patrick MacManus: 2 wds. |
| 40% | BRETMICHAELS | 12 | Poison singer who starred in "Rock of Love": 2 wds. |
| 40% | RODSTEWART | 10 | Singer who performed his song "Infatuation" to open the first MTV Video Music Awards, in 1984: 2 wds. |
| 40% | COREYHART | 9 | "Sunglasses at Night" singer, 1984 |