| 100% | CIARA | 5 | Singer of "1, 2 Step" and "Goodies" |
| 62% | ARIANAGRANDE | 12 | Singer of the #1 hits "Thank U, Next" and "7 Rings": 2 wds. |
| 62% | LADYGAGA | 8 | Singer of the #1 hits "Just Dance" and "Born This Way": 2 wds. |
| 59% | DIERKSBENTLEY | 13 | Singer of "Home" and 15-Across: 2 wds. |
| 59% | JUSTINBIEBER | 12 | Singer of 18-Across and 32-Across who turns 25 years old on March 1 (2 wds.) |
| 58% | ADD | 3 | Find the sum of 1 and 2 |
| 56% | CIARA | 5 | "1, 2 Step" singer |
| 55% | DIONNEWARWICK | 13 | Singer of many Burt Bacharach songs, including 34- and 44-Across: 2 wds. |
| 54% | SHIRLEYBASSEY | 13 | Singer of the James Bond theme songs "Goldfinger," "Diamonds Are Forever," and "Moonraker": 2 wds. |
| 54% | SARAHVAUGHAN | 12 | Jazz singer of the 1940s and 1950s nicknamed "The Divine One": 2 wds. |
| 53% | ARIE | 4 | "Testimony: Vol. 1" and "Testimony: Vol. 2" singer India |
| 53% | GLORIAESTEFAN | 13 | Songwriters Hall of Famer and Miami Sound Machine lead singer who was born September 1, 1957 (2 wds.) |
| 53% | WOOD | 4 | Step 1 of making a birdhouse: Cut ___ panels and fix the walls |
| 52% | GIMLETS | 7 | Cocktails of 2 parts gin and 1 part lime juice |
| 52% | CIARA | 5 | Collaborator with Missy Elliott on “1, 2 Step” and “Lose Control” |
| 52% | USHER | 5 | Singer of such #1 songs as "Yeah!" and "Burn" |
| 51% | PEARLBAILEY | 11 | Singer/actress who headlined versions of "Hello, Dolly!" in 1967 and 1975: 2 wds. |
| 51% | SHELLEYFABARES | 14 | Actress and singer who's the niece of 19-Across: 2 wds. |
| 51% | TRAVIS | 6 | Singer of the #1 country hit "Forever and Ever, Amen" |
| 51% | ARIANAGRANDE | 12 | Singer of the 2019 #1 hit "7 Rings": 2 wds. |
| 50% | CHAPPELLROAN | 12 | Singer with the debut album "The Rise and Fall of a Midwest Princess": 2 wds. |
| 50% | JAMESTAYLOR | 11 | Singer/songwriter who appeared on the March 1, 1971, cover of Time Magazine with the headline "The New Rock: Bittersweet and Low" (2 wds.) |
| 50% | BRIANWILSON | 11 | Pop singer who's the father of singers Wendy and Carnie: 2 wds. |
| 50% | CIARA | 5 | One-named collaborator with Missy Elliott on "1, 2 Step" and "Lose Control" |
| 50% | LUKEBRYAN | 9 | "Strip It Down" singer and 2015 CMA Entertainer of the Year: 2 wds. |
| 50% | PAPAROACH | 9 | "Buggy" singers of "Between Angels and Insects" (2 wds.) |
| 50% | DREWBARRYMORE | 13 | Unexpected singer of "Way Back Into Love" in 2007's "Music and Lyrics" (with Hugh Grant): 2 wds. |
| 50% | KATE | 4 | Singer and actress whose 2007 debut solo album, Made of Bricks, was a UK no 1 |
| 49% | KENNYCHESNEY | 12 | Singer of the 2007 #1 country hit "Beer in Mexico": 2 wds. |