| 100% | JHENEAIKO | 9 | 15-Across and 25-Down singer whose album 8-Down was recorded in and inspired by Hawaii (2 wds.) |
| 49% | ARLOPARKS | 9 | Grammy-nominated singer/songwriter whose songs 15-Across, 9-Down, and 27-Down are featured on her debut album, "Collapsed in Sunbeams" (2 wds.) |
| 46% | NORAHJONES | 10 | "Don't Know Why," 16-Across, 28-Across, and 35-Across singer whose ninth studio album was released in 2024 (2 wds.) |
| 46% | SARABAREILLES | 13 | 15-Across and 49-Across singer/songwriter whose new album "Amidst the Chaos" was released this month (2 wds.) |
| 45% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer-songwriter whose seventh studio album, "Eternal Sunshine," was released in 2024 (2 wds.) |
| 44% | EDSHEERAN | 9 | 15-Across, 28-Across, and 35-Across singer whose solo studio albums are all named with mathematical symbols (2 wds.) |
| 44% | ELVISCOSTELLO | 13 | "My Aim Is True" singer whose 2018 album "Look Now" features 15-Across and the 29-Across (2 wds.) |
| 43% | 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.) |
| 41% | JLO | 3 | Singer whose "This Is Me ... Now" album dropped in 2024, for short: 2 wds. |
| 41% | PETESEEGER | 10 | Folk singer whose anti-Vietnam War song on 15-/51-Across's show was censored by CBS: 2 wds. |
| 41% | DOLLYPARTON | 11 | Country singer whose latest album, "I Believe In You," is geared toward children: 2 wds. |
| 40% | LADYGAGA | 8 | 15-Across, 9-Down, and 22-Down singer who released the studio album "Mayhem" in 2025 (2 wds.) |
| 40% | ROYEMERSON | 10 | Australian tennis player whose record of six Australian Open wins was tied by 32-Across in 2016: 2 wds. |
| 40% | RAINBOWROWELL | 13 | 15-Across and 46-Across writer whose third "Simon Snow" novel was published in 2021 (2 wds.) |
| 40% | FLORIDA | 7 | Rapper and singer whose name comes from the state he was born in: 2 wds. |
| 40% | MILEYCYRUS | 10 | Singer whose 2008 album "Breakout" hit #1 when she was 15: 2 wds. |
| 40% | JONIMITCHELL | 12 | 15-Across and 44-Across singer-songwriter who was honored with a Gershwin Award in 2023 (2 wds.) |
| 39% | BETTEMIDLER | 11 | "Wind Beneath My Wings" singer who was born and raised in Hawaii: 2 wds. |
| 39% | LADYGAGA | 8 | Singer of 15-Across, 9-Down, and 22-Down who will appear in the 2018 remake of "A Star Is Born" (2 wds.) |
| 39% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 39% | BRUNOMARS | 9 | Singer of 15-Across and 29-Across who was born October 8, 1985 (2 wds.) |
| 39% | ELLIEGOULDING | 13 | 15-Across and 29-Across singer whose hit single "Love Me Like You Do" was nominated for a Grammy Award (2 wds.) |
| 39% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 39% | FIONAAPPLE | 10 | 18-Across, 25-Across, and 38-Across singer who released her fifth studio album "Fetch the Boltcutters" in 2020 (2 wds.) |
| 39% | COFFEESONG | 10 | "The ___," song written by Bob Hilliard and Dick Miles which was recorded by Frank Sinatra in 1946: 2 wds. |
| 39% | TRACYCHAPMAN | 12 | Singer whose song "Fast Car," from her self-titled debut album, was a #6 hit in 1988: 2 wds. |
| 38% | JIMIHENDRIX | 11 | "Purple Haze" guitarist and singer whose band was inducted into the Rock and Roll Hall of Fame in 1992: 2 wds. |
| 38% | MEGHANTRAINOR | 13 | Singer whose "All About That Bass" spent 25 weeks in the Billboard Top 10 in 2014 and 2015: 2 wds. |
| 37% | YOUBABY | 7 | 1966 song and album by 15-Across: 2 wds. |
| 37% | TIMRAINES | 9 | Outfielder whose #30 was retired by the Expos in 2004 and then unretired by the Nationals: 2 wds. |