| 100% | PAULSIMON | 9 | Singer whose 1986 hit album 36-Across was named for 28-Across's home (2 wds.) |
| 48% | EDSHEERAN | 9 | 15-Across, 28-Across, and 35-Across singer whose solo studio albums are all named with mathematical symbols (2 wds.) |
| 45% | DEMILOVATO | 10 | Singer whose 2009 album "Here We Go Again" hit #1 when she was 16: 2 wds. |
| 44% | MILEYCYRUS | 10 | Singer whose 2008 album "Breakout" hit #1 when she was 15: 2 wds. |
| 44% | JLO | 3 | Singer whose "This Is Me ... Now" album dropped in 2024, for short: 2 wds. |
| 43% | BRUNOMARS | 9 | Stage name for the "Uptown Funk" singer whose real name is Peter Gene Hernandez: 2 wds. |
| 43% | ALJARREAU | 9 | Singer whose "Moonlighting" was the theme song for the TV show of the same name: 2 wds. |
| 43% | HARRYSTYLES | 11 | "As It Was" singer whose 2022 album generated four simultaneous top 10 hits: 2 wds. |
| 43% | ANITABAKER | 10 | "Sweet Love" singer whose last name is a synonym for a pastry chef: 2 wds. |
| 42% | TRACYCHAPMAN | 12 | Singer whose song "Fast Car," from her self-titled debut album, was a #6 hit in 1988: 2 wds. |
| 42% | LADYGAGA | 8 | Stage name for the "Poker Face" singer whose real name is Stefani Joanne Angelina Germanotta: 2 wds. |
| 42% | JOEYFATONE | 10 | Former 'N Sync singer whose first name is also the term for a baby kangaroo: 2 wds. |
| 42% | LILNASX | 7 | Singer whose 2021 hit song "Montero (Call Me by Your Name)" is nominated for three Grammy Awards, including Record of the Year (3 wds.) |
| 42% | OLIVIARODRIGO | 13 | Singer whose 2021 hit single "Drivers License" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 42% | LUKECOMBS | 9 | Country singer whose cover of 27-Across's "Fast Car" was a #2 hit in 2023: 2 wds. |
| 41% | NORAHJONES | 10 | "Don't Know Why," 16-Across, 28-Across, and 35-Across singer whose ninth studio album was released in 2024 (2 wds.) |
| 40% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 40% | ELLIEGOULDING | 13 | 15-Across and 29-Across singer whose hit single "Love Me Like You Do" was nominated for a Grammy Award (2 wds.) |
| 40% | ELLIEGOULDING | 13 | 14-Across and 45-Across singer whose hit single "Love Me Like You Do" was nominated for a Grammy Award (2 wds.) |
| 40% | SARAHMCLACHLAN | 14 | Canadian singer of "Adia" whose name's only vowels are A's: 2 wds. |
| 40% | ROBINTHICKE | 11 | Singer whose 2013 #1 hit "Blurred Lines" was produced by Pharrell Williams: 2 wds. |
| 40% | DOJACAT | 7 | Singer whose 2021 hit single "Kiss Me More" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 40% | BRANDICARLILE | 13 | Singer whose 2021 hit song "Right on Time" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 39% | PAULACOLE | 9 | Singer whose "I Don't Want to Wait" was the theme song for "Dawson's Creek": 2 wds. |
| 39% | MIRANDALAMBERT | 14 | Singer whose "Wildcard" won the Grammy for Best Country Album in 2021: 2 wds. |
| 39% | DELREY | 6 | Singer Lana whose 2017 album "Lust for Life" was nominated for a Best Pop Vocal Album Grammy (2 wds.) |
| 39% | BILLYJOEL | 9 | "My Life" singer whose last name is a common first name: 2 wds. |
| 39% | ELTONJOHN | 9 | "Crocodile Rock" singer whose last name is a common first name: 2 wds. |
| 38% | TAYLORSWIFT | 11 | "Shake It Off" singer whose first name is a presidential last name: 2 wds. |
| 38% | LUKEBRYAN | 9 | "Play It Again" singer whose last name is a common first name: 2 wds. |