| 100% | CARLYRAEJEPSEN | 14 | "Call Me Maybe" singer who released her sixth studio album, "The Loneliest Time," in 2022 (3 wds.) |
| 55% | MEGHANTRAINOR | 13 | 18-Across, 40-Across, and "All About That Bass" singer who released her sixth studio album, "Timeless," in 2024 (2 wds.) |
| 44% | LADYGAGA | 8 | 15-Across, 9-Down, and 22-Down singer who released the studio album "Mayhem" in 2025 (2 wds.) |
| 44% | BRITNEYSPEARS | 13 | Pop singer who released the #1 album "… Baby One More Time" in 1999, at age 17: 2 wds. |
| 44% | FIONAAPPLE | 10 | 18-Across, 25-Across, and 38-Across singer who released her fifth studio album "Fetch the Boltcutters" in 2020 (2 wds.) |
| 44% | CARLYRAEJEPSEN | 14 | "Call Me Maybe" singer who performed in Fox's 2016 "Grease Live!": 3 wds. |
| 43% | JEWEL | 5 | Singer who released her "Picking Up the Pieces" album in 2015 |
| 42% | CAREY | 5 | Singer Mariah who released her 15th studio album in 2018 |
| 41% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 41% | SOLANGE | 7 | American singer who released the album "When I Get Home" in 2019 |
| 40% | RAEJEPSEN | 9 | Carly, singer who had The Loneliest Time in 2022 |
| 39% | GEORGESTRAIT | 12 | 18-Across and 29-Across singer who released his 30th studio album, "Honky Tonk Time Machine," in 2019 (2 wds.) |
| 39% | MARYJBLIGE | 10 | Singer who made up the word "hateration" in her 2001 hit "Family Affair": 3 wds. |
| 39% | JUSTINBIEBER | 12 | Pop singer who released the #1 album "My World 2.0" in 2010, at age 16: 2 wds. |
| 37% | STEVIEWONDER | 12 | R&B singer who released the #1 album "Recorded Live: The 12 Year Old Genius" in 1963, at age 13: 2 wds. |
| 36% | TAYLORSWIFT | 11 | American singer who created hits like "Blank Space" and "Bad Blood," and releases her newest album on the 10th: 2 wds. |
| 36% | SYD | 3 | Single named singer who released her debut R&B album "Fin" in February 2017 |
| 35% | BLAKE | 5 | James ___, English singer who released the album "Assume Form" in 2019 |
| 35% | CAMILACABELLO | 13 | Cuban-American singer-songwriter who released her first solo album in 2018 (2 wds.) |
| 35% | ARIANA | 6 | ___ Grande, American singer who released the album "Thank U, Next" in 2019 |
| 35% | SZA | 3 | Singer who released her sophomore album, “SOS,” more than five years after her critically acclaimed début, “Ctrl” (December, 2022) |
| 35% | SCARLETT | 8 | ___ Johansson, "The Avengers" actress who released her debut album "Anywhere I Lay My Head" in 2008 |
| 35% | LANADELREY | 10 | "Doin' Time" singer who collaborates with 27-Across and 35-Across on the 2019 "Charlie's Angels" theme song "Don't Call Me Angel" (3 wds.) |
| 35% | LEA | 3 | Actress and Singer ___ Michele, who released her third album, "Christmas in the City" in 2019 |
| 34% | NEILYOUNG | 9 | Canadian-born singer who released "Rockin' in the Free World" in 1989: 2 wds. |
| 34% | ARI | 3 | Singer who recently released the "Thank U, Next" studio album, for short |
| 34% | JACKHARLOW | 10 | 17-Across, 28-Across, and "Whats Poppin" rapper who released his second studio album, "Come Home the Kids Miss You," in 2022 (2 wds.) |
| 34% | BRITNEYSPEARS | 13 | Singer who appears nude in the video of her 2008 single, "Womanizer": 2 wds. |
| 33% | NAS | 3 | Rapper who released the albums "Magic 2" and "Magic 3" in 2023 |
| 33% | JANELLEMONAE | 12 | Singer who featured the android character Cindi Mayweather on her 2010 "The ArchAndroid" concept album: 2 wds. |