| 100% | PAULMCCARTNEY | 13 | 15-Across, 27-Across, and 36-Across singer/songwriter born June 18, 1942 (2 wds.) |
| 60% | PAULMCCARTNEY | 13 | The Beatles and Wings singer-songwriter who was born June 18, 1942 (2 wds.) |
| 55% | KATYPERRY | 9 | 15-Across, 9-Down, and 27-Down singer born on October 25, 1984 (2 wds.) |
| 51% | ALICIAKEYS | 10 | 18-Across and 31-Across singer-songwriter who was born January 25, 1981 (2 wds.) |
| 50% | BEBEREXHA | 9 | Singer who performed on 15-, 27-, and 34-Across: 2 wds. |
| 47% | DAVIDBOWIE | 10 | Singer of 18-Across, 27-Across, and 35-Across (January 8, 1947-January 10, 2016) (2 wds.) |
| 47% | MAHERSHALAALI | 13 | 15-Across, 27-Across, and 36-Across actor whose first major role was on TV's "Crossing Jordan" (2 wds.) |
| 46% | BLAKESHELTON | 12 | Longtime coach on "The Voice" and country music singer who was born June 18, 1976 (2 wds.) |
| 45% | BRUNOMARS | 9 | Singer of 15-Across and 29-Across who was born October 8, 1985 (2 wds.) |
| 45% | BLAKESHELTON | 12 | "God's Country" singer who was born June 18, 1976 (2 wds.) |
| 43% | DIERKSBENTLEY | 13 | Singer of "Home" and 15-Across: 2 wds. |
| 43% | NEILYOUNG | 9 | 15-Across, 20-Across, and 34-Across singer/songwriter who turns 75 years old today (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% | JENNIFERLOPEZ | 13 | 15-Across and 27-Across singer who was the first woman honored with a "Billboard" Icon Award (2 wds) |
| 42% | JOHNSTEINBECK | 13 | Nobel Prize-winning writer born February 27, 1902, who wrote 18-Across and 44-Across (2 wds.) |
| 42% | 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.) |
| 41% | 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.) |
| 41% | TOMPETTY | 8 | "Free Fallin'" singer/songwriter who cowrote and performed 34-Across: 2 wds. |
| 41% | GRACIEABRAMS | 12 | 18-Across and 32-Across singer-songwriter who often opens for Taylor Swift on her Eras Tour (2 wds.) |
| 40% | STLOUIS | 7 | City where 18-Across played ... and where 44-Across was born: 2 wds. |
| 40% | HARRYCONNICKJR | 14 | 19-Across and 44-Across singer-songwriter born September 11, 1967 (3 wds.) |
| 40% | PAULMCCARTNEY | 13 | 15-Across and 31-Across singer/songwriter with 18 Grammy Awards, an Academy Award, and two inductions into the Rock and Roll Hall of Fame who turns 80 years old this week (2 wds.) |
| 40% | JUSTINBIEBER | 12 | "Peaches" singer/songwriter who co-wrote and sings 36-Across with 17-Across (2 wds.) |
| 40% | IANMCEWAN | 9 | 15-Across and 31-Across novelist who turns 75 on June 21, 2023 (2 wds.) |
| 40% | ANDERSONCOOPER | 14 | CNN journalist born June 3, 1967, who was a guest on 16-Across at age three and 36-Across at age nine (2 wds.) |
| 39% | JONIMITCHELL | 12 | 15-Across and 44-Across singer-songwriter who was honored with a Gershwin Award in 2023 (2 wds.) |
| 39% | GLORIAESTEFAN | 13 | Songwriters Hall of Famer and Miami Sound Machine lead singer who was born September 1, 1957 (2 wds.) |
| 39% | BILLYIDOL | 9 | 15-Across, 21-Across, and 34-Across singer who turns 65 on November 30 (2 wds.) |
| 39% | POSTMALONE | 10 | 18-Across, 27-Across, and 34-Across rapper/singer who won the 2025 American Music Award for Favorite Country Male Artist (2 wds.) |
| 39% | LOUISARMSTRONG | 14 | Jazz trumpeter and singer born in New Orleans: 2 wds. |