| 100% | CHER | 4 | Singer with ''Billboard'' #1s in '74 and '99 |
| 57% | ENYA | 4 | Mononymous singer with recordings in Irish and Elvish |
| 56% | SADE | 4 | One-named singer with Grammys in 1985 and 2010 |
| 56% | JANELLEMONAE | 12 | Grammy-nominated singer with roles in "Moonlight" and "Hidden Figures" |
| 55% | CHER | 4 | Singer with #1 hits in the '60s, '70s, '80s and '90s |
| 54% | USHER | 5 | Singer with the #1 hits "Yeah!" and "Love in This Club" |
| 53% | ERIC | 4 | ___ Church, country singer with the #1 hits "Drink in My Hand" and "Springsteen" |
| 53% | CHER | 4 | Singer with top 10 hits in the 1960's, 70's, 80's and 90's |
| 52% | ETHELMERMAN | 11 | ... and 99-Across starred in musicals and share their first names with a classic sitcom couple |
| 51% | MEANDER | 7 | With 74-Across, Like St. Petersburg in 1914, 1924 and 1991 * Drift aimlessly |
| 51% | MONAE | 5 | Singer Janelle with roles in "Moonlight" and "Hidden Figures" |
| 50% | CHER | 4 | One-named singer with #1 hits in 1965 and 1999 |
| 50% | LULU | 4 | Singer and actress who played Barbara Pegg in 1967 film drama To Sir, with Love |
| 50% | SHEENAEASTON | 12 | "Strut" singer who Prince encouraged and collaborated with in the 1980s: 2 wds. |
| 49% | JEWEL | 5 | Singer and actress who played Sue Lee Shelley in 1999 film drama Ride with the Devil |
| 49% | LAINE | 5 | Singer Cleo with Grammy nominations in jazz, pop and classical |
| 47% | GEORGECLINTON | 13 | Singer with Parliament and Funkadelic |
| 47% | NASH | 4 | Singer with Crosby and Stills |
| 47% | ELLA | 4 | Singer with Count and Duke |
| 47% | ELLA | 4 | Singer with Duke and Count |
| 47% | ARIANA | 6 | With 35-Across, "Problem" singer featured on three songs in Billboard's top 10 during a week in 2014 |
| 47% | ISLANDSIN | 9 | With 40-Across, song that reached #1 on Billboard's country and Hot 100 charts in 1983: 2 wds. |
| 47% | MONROE | 6 | Marilyn ___, yesteryear actress and singer who worked with WAIF, an organization that placed abandoned children in homes |
| 46% | CROSBY | 6 | Singer with Stills, Nash and Young |
| 46% | EDSHEERAN | 9 | Singer with hit albums +, x and = |
| 46% | ARIANAGRANDE | 12 | "Yes, And?" singer who had two songs reach #1 on the Billboard Hot 100 in 2024: 2 wds. |
| 46% | JONIMITCHELL | 12 | 15-Across and 44-Across singer-songwriter who was honored with a Gershwin Award in 2023 (2 wds.) |
| 46% | ADELE | 5 | Singer with albums "19," "21" and "25" |
| 45% | WINEHOUSE | 9 | Singer with albums Frank and Back to Black |