| 100% | SIA | 3 | Singer of “Satisfied” on “The Hamilton Mixtape” |
| 64% | BENHARPER | 9 | Singer of Diamonds on the Inside |
| 58% | EDDIEMONEY | 10 | Singer of the Top 10 hit "Walk on Water" |
| 58% | DAVIDCOOK | 9 | Singer of the 2008 song "Light On": 2 wds. |
| 58% | OTIS | 4 | "Sitting on the dock of the Bay" singer |
| 56% | OTIS | 4 | "Sitting on the dock of the Bay" singer, first name |
| 56% | SIA | 3 | One-named singer of "Unforgettable" on the "Finding Dory" soundtrack |
| 56% | AMII | 4 | ___ Stewart, singer of the 1979 #1 hit "Knock on Wood" |
| 56% | REDDING | 7 | "(Sittin' On) The Dock of the Bay" singer |
| 56% | OTISREDDING | 11 | "(Sittin' On) The Dock of the Bay" singer |
| 56% | LOU | 3 | ___ Reed, singer of "Walk on the Wild Side" |
| 56% | LORDE | 5 | Singer on the remix of "Girl, So Confusing" |
| 55% | OTIS | 4 | "(Sittin' On) The Dock of the Bay" singer Redding |
| 55% | OTIS | 4 | ___ Redding, "(Sittin' On) The Dock of the Bay" singer |
| 55% | OTIS | 4 | “(Sittin’ On) The Dock of the Bay” singer Redding |
| 54% | OTIS | 4 | “(Sittin’ On) The Dock of the Bay” singer-songwriter Redding |
| 53% | PAULAABDUL | 10 | Singer who was one of the original judges on "American Idol" |
| 53% | RAMOS | 5 | Actor who originated the role of Hamilton on Broadway |
| 53% | LOU | 3 | Singer ___ Reed of "Walk On The Wild Side" |
| 52% | ELMO | 4 | One of the "Bye Bye Binky" singers on "Sesame Street" |
| 52% | PAULMCCARTNEY | 13 | One of the two singers on 15-Across: 2 wds. |
| 52% | MICKJAGGER | 10 | Lead singer of the Rolling Stones who turned 77 on July 26, 2020 (2 wds.) |
| 52% | MYA | 3 | One of the singers on 2001's #1 hit "Lady Marmalade" |
| 52% | MICHAEL | 7 | With 33-Across, one of the two singers on 15-Across |
| 51% | RAY | 3 | Biopic about the singer of "Georgia on My Mind" |
| 51% | JOHNLEGEND | 10 | "All of Me" singer who performed "History Has Its Eyes on You" on "The Hamilton Mixtape": 2 wds. |
| 51% | CHARLIXCX | 9 | Singer featured on the chorus of the 2012 hit "I Love It" |
| 51% | BRITNEYSPEARS | 13 | Singer of "Womanizer," which jumped 95 spots to #1 on the charts in one week in 2008: 2 wds. |
| 51% | RIHANNA | 7 | Singer of "Take a Bow," which jumped 52 spots to #1 on the charts in one week in 2008 |
| 50% | JOANBAEZ | 8 | *Singer on the first day of Woodstock |