| 100% | BRYAN | 5 | With 36-Across, "Summer of '69" singer with the 1985 song "Heaven" |
| 63% | BRYANADAMS | 10 | Singer with the 1985 top 10 hit "Summer of '69": 2 wds. |
| 56% | ARLO | 4 | With 23-Across, singer of the song referenced at 6-Down |
| 53% | PATSY | 5 | With 33-Across, singer of "Crazy," the 1992 campaign song for H. Ross Perot |
| 53% | SADE | 4 | Singer of the 1985 song "The Sweetest Taboo" |
| 51% | HER | 3 | One-named singer with the 2019 Song of the Year nominee "Hard Place" |
| 51% | PETERCETERA | 11 | Singer with the 1986 #1 song “Glory of Love”: 2 wds. |
| 51% | BRYANADAMS | 10 | Canadian singer known for the hit songs "Summer of '69" and "Heaven" (2 wds.) |
| 51% | ERICCLAPTON | 11 | "I Shot the Sheriff" singer with the 1992 song "Tears in Heaven": 2 wds. |
| 51% | KATYPERRY | 9 | Starting in 2010, pop singer with a song in the top 10 of the Billboard Hot 100 for 69 consecutive weeks: 2 wds. |
| 51% | PHILCOLLINS | 11 | Singer with the 1988 #1 song “Groovy Kind of Love”: 2 wds. |
| 51% | THEFIRSTTIMEEVERI | 17 | With 127 Across, the best-selling hat song of 1972? |
| 50% | DOLLYPARTONS | 12 | With 27-Across, Netflix anthology series dramatizing the stories behind some of a singer's songs: 2 wds. |
| 49% | MANN | 4 | Singer Aimee with the 2021 album "Queens of the Summer Hotel" |
| 48% | ENYA | 4 | Singer with an Oscar-nominated song in "The Lord of the Rings" |
| 48% | TOMORROWISALONG | 15 | With 69 Across, Bob Dylan song about the future |
| 47% | SZA | 3 | Singer with the 2024 song "Saturn" |
| 46% | SADE | 4 | Singer with the 1985 hit "Smooth Operator" |
| 46% | EDGE | 4 | "Music from the ___ of Heaven," 1986 album from Wham! with the song "Last Christmas" |
| 46% | ROBERT | 6 | With 30-Across, singer with the 1986 #1 song “Addicted to Love" |
| 46% | MILEY | 5 | With 34-Across, singer of the 2008 top 10 hit "7 Things" |
| 46% | SAM | 3 | ___ Smith, singer of the massive hit song "Stay With Me" |
| 46% | IFMY | 4 | With 36- and 43-Across, second line of the poem |
| 46% | SOLONG | 6 | With 20 Across, "The Sound of Music" song |
| 46% | YOGI | 4 | With 36 Across, source of quote |
| 45% | DAVIDLEEROTH | 12 | Singer with the 1985 #3 Billboard hit "California Girls" |
| 45% | STEVEN | 6 | With 69-Across, asker of the question |
| 45% | MONLAFERTE | 10 | Chilean singer with the hit song "Amarrame" |
| 44% | ADELE | 5 | First solo female singer with three songs in the top 10 of the Billboard Hot 100 simultaneously |
| 44% | TRIPLE | 6 | With 36-Across, statistical feat that typically involves the number of points, rebounds, and assists |