| 100% | BRYANADAMS | 10 | "Summer of '69" singer (2 wds.) |
| 80% | BRYANADAMS | 10 | "Summer of 69" artist who wrote the soundtrack for the film "Spirit: Stallion of the Cimarron" alongside Hans Zimmer: 2 wds. |
| 78% | EDSHEERAN | 9 | "Shape of You" singer: 2 wds. |
| 78% | ASHLEESIMPSON | 13 | "Pieces of Me" singer: 2 wds. |
| 75% | BRYANADAMS | 10 | Singer with the 1985 top 10 hit "Summer of '69": 2 wds. |
| 74% | WEIRDAL | 7 | Nickname of parody singer Yankovic: 2 wds. |
| 74% | BRYANADAMS | 10 | Canadian singer known for the hit songs "Summer of '69" and "Heaven" (2 wds.) |
| 72% | MORGANWALLEN | 12 | Singer of the 2020 top 10 hit "7 Summers": 2 wds. |
| 70% | JESSIEJ | 7 | British singer of "Domino": 2 wds. |
| 70% | ELLAHENDERSON | 13 | British singer of "Ghost": 2 wds. |
| 70% | NELLYFURTADO | 12 | Canadian singer of "Promiscuous": 2 wds. |
| 69% | SHIRLEYMANSON | 13 | Female lead singer of Garbage: 2 wds. |
| 68% | ADAMS | 5 | "Summer of '69" singer Bryan |
| 67% | PATRICKSTUMP | 12 | Lead singer of 17-Across: 2 wds. |
| 67% | TAYLORSWIFT | 11 | "Cruel Summer" singer (2 wds.) |
| 66% | CHRISSIEHYNDE | 13 | Female lead singer of the Pretenders: 2 wds. |
| 66% | BRADPAISLEY | 11 | "Beat This Summer" singer (2 wds.) |
| 65% | JLO | 3 | Nickname of the singer known for "All I Have" and "On the Floor": 2 wds. |
| 65% | SAMUELBARBER | 12 | "Adagio for Strings" artist who won Pulitzer Prize for Music twice and is widely known for "Knoxville: Summer of 1915": 2 wds. |
| 65% | KATYCATS | 8 | Fans of the "California Gurls" singer: 2 wds. |
| 65% | ANDREABOCELLI | 13 | Visually impaired singer of "The Prayer": 2 wds. |
| 65% | JOSEFELICIANO | 13 | Visually impaired singer of "Feliz Navidad": 2 wds. |
| 64% | ISEE | 4 | 2 wds to show understanding of something |
| 64% | FRANKSINATRA | 12 | One of two singers to win 33-Across three times as a solo artist: 2 wds. |
| 64% | STEVIEWONDER | 12 | One of two singers to win 33-Across three times as a solo artist: 2 wds. |
| 63% | ELLIEGOULDING | 13 | Singer of the 2011 song "Lights": 2 wds. |
| 62% | FRANKZAPPA | 10 | Lead singer of the Mothers of Invention: 2 wds. |
| 62% | PAULSIMON | 9 | One of the singers of "Bridge Over Troubled Water," the 1972 campaign song for George McGovern: 2 wds. |
| 62% | BRITNEYSPEARS | 13 | "Toxic" singer: 2 wds. |
| 61% | LITTLEMONSTERS | 14 | Fans of the "Born This Way" singer: 2 wds. |