| 100% | 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.) |
| 43% | OLIVIARODRIGO | 13 | "Bizaardvark" star whose hit songs 14-Across, 18-Across, and 43-Across/52-Across are on her debut album "Sour" (2 wds.) |
| 43% | KATYPERRY | 9 | 15-Across, 9-Down, and 27-Down singer who flew into space on a Blue Origin flight in 2025 (2 wds.) |
| 43% | TRACYCHAPMAN | 12 | Singer whose song "Fast Car," from her self-titled debut album, was a #6 hit in 1988: 2 wds. |
| 41% | KATYPERRY | 9 | 15-Across, 9-Down, and 27-Down singer born on October 25, 1984 (2 wds.) |
| 41% | LADYGAGA | 8 | 15-Across, 9-Down, and 22-Down singer who released the studio album "Mayhem" in 2025 (2 wds.) |
| 40% | JHENEAIKO | 9 | 15-Across and 25-Down singer whose album 8-Down was recorded in and inspired by Hawaii (2 wds.) |
| 38% | LADYGAGA | 8 | Singer-songwriter whose song "Shallow" from the movie "A Star Is Born" won her an Oscar in 2018: 2 wds. |
| 38% | ELVISCOSTELLO | 13 | "My Aim Is True" singer whose 2018 album "Look Now" features 15-Across and the 29-Across (2 wds.) |
| 37% | ELLIEGOULDING | 13 | 15-Across and 29-Across singer whose hit single "Love Me Like You Do" was nominated for a Grammy Award (2 wds.) |
| 37% | ANDREABOCELLI | 13 | Italian classical singer whose album "Cinema" was nominated for Best Traditional Pop Vocal Album in the 2017 Grammy Awards : 2 wds. |
| 37% | MILEYCYRUS | 10 | 17-Across and 27-Across singer whose 2023 single "Flowers" debuted at No. 1 on the "Billboard" Global 200 chart in 2023 (2 wds.) |
| 37% | 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.) |
| 36% | IGGYAZALEA | 10 | "Fancy" singer featured on "Problem" who in 2014 became the second ever to be simultaneously #1 and #2 with her first two hits: 2 wds. |
| 36% | SARABAREILLES | 13 | 15-Across and 49-Across singer/songwriter whose new album "Amidst the Chaos" was released this month (2 wds.) |
| 36% | ARIANAGRANDE | 12 | 17-Across and 39-Across singer-songwriter whose seventh studio album, "Eternal Sunshine," was released in 2024 (2 wds.) |
| 36% | CELINEDION | 10 | Singer whose 1998 song "My Heart Will Go On" debuted at #1: 2 wds. |
| 35% | PETESEEGER | 10 | Folk singer whose anti-Vietnam War song on 15-/51-Across's show was censored by CBS: 2 wds. |
| 35% | MILEYCYRUS | 10 | Singer whose 2008 album "Breakout" hit #1 when she was 15: 2 wds. |
| 35% | BRANDICARLILE | 13 | Singer whose 2021 hit song "Right on Time" is nominated for three Grammy Awards, including Record of the Year (2 wds.) |
| 35% | THEWEEKND | 9 | Canadian singer whose "Blinding Lights" was the #1 song on Spotify in 2020: 2 wds. |
| 35% | BEBEREXHA | 9 | Singer who performed on 15-, 27-, and 34-Across: 2 wds. |
| 35% | EDWARDHOPPER | 12 | American artist whose paintings "Nighthawks" and "Automat" were featured on U.S. postage stamps in 1998 (2 wds.) |
| 34% | MAGGIEROGERS | 12 | Singer/songwriter whose big break came when a video featuring Pharrell Williams listening to her song "Alaska" went viral in 2016 (2 wds.) |
| 34% | EDSHEERAN | 9 | English singer whose album "÷" and song "Shape of You" both topped the charts in 2017: 2 wds. |
| 34% | MAHERSHALAALI | 13 | 15-Across, 27-Across, and 36-Across actor whose first major role was on TV's "Crossing Jordan" (2 wds.) |
| 34% | JOHNFOGERTY | 11 | Singer/songwriter whose song 17-Across was honored by the Baseball Hall of Fame in 2010 (2 wds.) |
| 34% | CYNDILAUPER | 11 | Singer/songwriter whose first #1 hit song was 15-Across (2 wds.) |
| 34% | DOLLYPARTON | 11 | "9 to 5" actress/singer whose "The Grass Is Blue" won the Best Bluegrass Album Grammy in 2001: 2 wds. |
| 34% | DIANAROSS | 9 | American singer who was the lead singer of "The Supremes" and is known for her solo songs like "Upside Down": 2 wds. |