| 100% | JASONISBELL | 11 | Grammy-winning singer-songwriter on 11-Across and 24-Across (2 wds.) |
| 59% | PEABOBRYSON | 11 | Singer/songwriter who won Grammy Awards for 34-Across and the "Beauty and the Beast" theme (2 wds.) |
| 58% | REBAMCENTIRE | 12 | Grammy-winning country star who plays a singer on 32-Across: 2 wds. |
| 57% | BEBEREXHA | 9 | Singer who performed on 15-, 27-, and 34-Across: 2 wds. |
| 56% | AVRILLAVIGNE | 12 | Eight-time Grammy-nominated singer/songwriter of 16-Across and 48-Across (2 wds.) |
| 56% | 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.) |
| 55% | EMMYLOUHARRIS | 13 | Country Music Hall of Fame singer who collaborated with 28-Across and 43-Across on the Grammy-winning 1987 album "Trio" (2 wds.) |
| 54% | LORNEMICHAELS | 13 | Seth Meyers' executive producer on 24- and 29-Across: 2 wds. |
| 54% | LIZAMINNELLI | 12 | "Cabaret" star and singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 53% | WILLIENELSON | 12 | "Always on My Mind" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 53% | FIONAAPPLE | 10 | Grammy-winning singer who performs the theme song "Container" on "The Affair": 2 wds. |
| 52% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 52% | RITAMORENO | 10 | Emmy, Grammy, Oscar, and Tony winner who stars on 32-Across: 2 wds. |
| 52% | BILLYPRESTON | 12 | Singer who sang with Nat King Cole on a TV show at 11 and released his first album at 16: 2 wds. |
| 52% | DARKBLUE | 8 | Color on the spaces for 24- and 42-Across: 2 wds. |
| 52% | WHITNEYHOUSTON | 14 | Emmy- and Grammy-winning singer and actress who would've turned 60 years old on August 9, 2023 (2 wds.) |
| 52% | PATTYLOVELESS | 13 | "Blame It on Your Heart" singer whose "Mountain Soul II" won the Best Bluegrass Album Grammy in 2011: 2 wds. |
| 51% | TOMPETTY | 8 | "Free Fallin'" singer/songwriter who cowrote and performed 34-Across: 2 wds. |
| 51% | BRANDICARLILE | 13 | 18-Across and 42-Across singer who won a Best Country Song Grammy Award for "Bring My Flowers Now" (2 wds.) |
| 51% | FRANKSINATRA | 12 | Grammy- and Oscar-winning singer/actor who was born 100 years ago today: 2 wds. |
| 50% | SAMSMITH | 8 | Grammy-winning singer of "Stay With Me," 15-Across, 20-Across, and 37-Across (2 wds.) |
| 50% | DAMIANMCGINTY | 13 | Irish singer who played Rory Flanagan on "Glee" and was a member of 32-Across: 2 wds. |
| 49% | AMYPOEHLER | 10 | "Saturday Night Live" comedian who went on to star in 24-Across and 36-/42-Across: 2 wds. |
| 48% | LADYGAGA | 8 | Singer who won a 2011 Grammy for "Bad Romance": 2 wds. |
| 48% | JEFFDANIELS | 11 | Actor who won a 2013 Emmy for playing Will McAvoy, the anchor and managing editor on 37-Across: 2 wds. |
| 48% | BLAKESHELTON | 12 | Country singer and judge on "The Voice": 2 wds. |
| 48% | LOUISARMSTRONG | 14 | Jazz singer and trumpeter who collaborated with 34-Across on three albums, including "Porgy and Bess": 2 wds. |
| 48% | STEPHENSTILLS | 13 | American singer and songwriter who is the first artist to be inducted twice on the same night into the Rock and Roll Hall of Fame: 2 wds. |
| 48% | FIONAAPPLE | 10 | Art pop singer-songwriter who won a Best Alternative Music Album Grammy in 2021 for "Fetch the Bolt Cutters": 2 wds. |
| 48% | RAVISHANKAR | 11 | Sitar maestro who collaborated with "The Beatles" and who is the father of multiple Grammy-winning singer Norah Jones: 2 wds. |