| 100% | MEGHANTRAINOR | 13 | 18-Across, 40-Across, and "All About That Bass" singer who released her sixth studio album, "Timeless," in 2024 (2 wds.) |
| 59% | MEGHANTRAINOR | 13 | 18-Across, 40-Across, and "All About That Bass" singer who has won two "Billboard" Music Awards and a "Billboard" Women in Music Chart-Topper Award (2 wds.) |
| 58% | FIONAAPPLE | 10 | 18-Across, 25-Across, and 38-Across singer who released her fifth studio album "Fetch the Boltcutters" in 2020 (2 wds.) |
| 50% | GEORGESTRAIT | 12 | 18-Across and 29-Across singer who released his 30th studio album, "Honky Tonk Time Machine," in 2019 (2 wds.) |
| 48% | CARLYRAEJEPSEN | 14 | "Call Me Maybe" singer who released her sixth studio album, "The Loneliest Time," in 2022 (3 wds.) |
| 45% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |
| 44% | LADYGAGA | 8 | 15-Across, 9-Down, and 22-Down singer who released the studio album "Mayhem" in 2025 (2 wds.) |
| 44% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer-songwriter whose seventh studio album, "Eternal Sunshine," was released in 2024 (2 wds.) |
| 44% | DIANAROSS | 9 | 15-Across, 21-Across, and 40-Across singer who digitally released her new remix collection "Supertonic: Mixes" in 2020 (2 wds.) |
| 42% | MEGHANTRAINOR | 13 | Singer whose "All About That Bass" spent 25 weeks in the Billboard Top 10 in 2014 and 2015: 2 wds. |
| 42% | NORAHJONES | 10 | "Don't Know Why," 16-Across, 28-Across, and 35-Across singer whose ninth studio album was released in 2024 (2 wds.) |
| 41% | KENNYCHESNEY | 12 | Country music superstar who released his 20th studio album, "Born," in 2024 (2 wds.) |
| 41% | SHERYLCROW | 10 | Rock & Roll Hall of Fame singer of 14-Across and 38-Across whose 12th studio album, "Evolution," was released in 2024 (2 wds.) |
| 40% | DAVIDBOWIE | 10 | "Fame" and "Let's Dance" rock legend who released his first studio album in a decade in March: 2 wds. |
| 39% | CAREY | 5 | Singer Mariah who released her 15th studio album in 2018 |
| 38% | CAMILACABELLO | 13 | Cuban-American singer-songwriter who released her first solo album in 2018 (2 wds.) |
| 38% | MEGHANTRAINOR | 13 | "All About That Bass" singer-songwriter who recorded the duet "White Christmas" with 32-Across (2 wds.) |
| 37% | MEGHANTRAINOR | 13 | Singer whose debut single "All About That Bass" reached #1 on the Billboard Hot 100 in 2014: 2 wds. |
| 37% | 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.) |
| 37% | BILLIEEILISH | 12 | Singer who released "Birds of a Feather" in 2024: 2 wds. |
| 37% | TAYLORSWIFT | 11 | American singer who created hits like "Blank Space" and "Bad Blood," and releases her newest album on the 10th: 2 wds. |
| 35% | ARIANAGRANDE | 12 | "7 Rings" singer who reimagined 18-Across in a 2024 hit with the same title: 2 wds. |
| 35% | HARRYSTYLES | 11 | "Sign of the Times" pop singer who released a self-titled #1 album in 2017: 2 wds. |
| 35% | LEA | 3 | Actress and Singer ___ Michele, who released her third album, "Christmas in the City" in 2019 |
| 35% | KEMBAWALKER | 11 | Hornets and Celtics NBA All-Star guard who retired in 2024: 2 wds. |
| 35% | GORDONHAYWARD | 13 | Jazz and Hornets NBA All-Star forward who retired in 2024: 2 wds. |
| 35% | DERRICKROSE | 11 | Bulls and Knicks NBA All-Star guard who retired in 2024: 2 wds. |
| 35% | SELENAGOMEZ | 11 | 18-Across and 30-Across singer who plays Mabel Mora on "Only Murders in the Building" (2 wds.) |
| 34% | PAULMCCARTNEY | 13 | Singer and bass guitarist for the Beatles who was knighted in 1997: 2 wds. |
| 34% | PHILCOLLINS | 11 | "Against All Odds" singer who retired in 2011 and unretired in 2015: 2 wds. |