| 100% | AVRILLAVIGNE | 12 | Canadian-born singer who released "Sk8er Boi" in 2002: 2 wds. |
| 69% | JUSTINBIEBER | 12 | Canadian-born singer who released "Boyfriend" in 2012: 2 wds. |
| 68% | COREYHART | 9 | Canadian-born singer who released "Sunglasses at Night" in 1984: 2 wds. |
| 67% | NEILYOUNG | 9 | Canadian-born singer who released "Rockin' in the Free World" in 1989: 2 wds. |
| 57% | BILLIEEILISH | 12 | Singer who released "Birds of a Feather" in 2024: 2 wds. |
| 55% | NELLYFURTADO | 12 | Singer who released "I'm Like a Bird" in 2000: 2 wds. |
| 52% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 51% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 51% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 50% | LEANNRIMES | 10 | "Blue" singer who performed in the 2002 Salt Lake City Winter Olympics opening ceremony: 2 wds. |
| 50% | OZZYOSBOURNE | 12 | Heavy metal singer who starred in a 2002-2005 MTV reality show about his family: 2 wds. |
| 49% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 47% | LADYGAGA | 8 | 15-Across, 9-Down, and 22-Down singer who released the studio album "Mayhem" in 2025 (2 wds.) |
| 46% | KELLYCLARKSON | 13 | "Piece by Piece" singer who got her start on "American Idol" in 2002: 2 wds. |
| 46% | PAULMCCARTNEY | 13 | Singer who came up with "Yesterday" in his sleep: 2 wds. |
| 46% | DIANAROSS | 9 | Singer who played Dorothy in 1978's "The Wiz": 2 wds. |
| 46% | GEORGESTRAIT | 12 | 18-Across and 29-Across singer who released his 30th studio album, "Honky Tonk Time Machine," in 2019 (2 wds.) |
| 46% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who was born and raised in Hawaii: 2 wds. |
| 46% | BRITNEYSPEARS | 13 | "Toxic" singer who hosted and performed on "SNL" in 2000 and 2002: 2 wds. |
| 45% | FIONAAPPLE | 10 | 18-Across, 25-Across, and 38-Across singer who released her fifth studio album "Fetch the Boltcutters" in 2020 (2 wds.) |
| 45% | MEGHANTRAINOR | 13 | 18-Across, 40-Across, and "All About That Bass" singer who released her sixth studio album, "Timeless," in 2024 (2 wds.) |
| 45% | AMBERRILEY | 10 | Singer who played Addaperle in "The Wiz Live!": 2 wds. |
| 45% | TINATURNER | 10 | "Private Dancer" singer who was born Anna Mae Bullock: 2 wds. |
| 45% | SHAWNMENDES | 11 | "Señorita" singer who voices Lyle in "Lyle, Lyle, Crocodile": 2 wds. |
| 44% | LENAHORNE | 9 | Singer who played Glinda the Good Witch in "The Wiz": 2 wds. |
| 44% | ELVISCOSTELLO | 13 | "Veronica" singer who was born Declan Patrick MacManus: 2 wds. |
| 44% | FETTYWAP | 8 | "Trap Queen" singer who won 14-Across in 2016: 2 wds. |
| 44% | BRETMICHAELS | 12 | Poison singer who starred in "Rock of Love": 2 wds. |
| 44% | QUEENLATIFAH | 12 | Singer who played the Wiz in "The Wiz Live!": 2 wds. |
| 43% | BRITNEYSPEARS | 13 | Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds. |