| 100% | CHER | 4 | Singer with Top Ten hits four decades in a row |
| 47% | CHER | 4 | Female singer with a hit album in every decade since the 1960s |
| 44% | CHER | 4 | One-named singer with Top 10 hits in each decade from the 1960s to the 2010s |
| 44% | CHER | 4 | One-named singer with Top 10 hits in each decade from the 1960s to the 2020s |
| 43% | ALOE | 4 | Singer ___ Blacc who had a top-10 hit in 2014 with "The Man" |
| 40% | CHER | 4 | Singer with top 10 hits in the 1960's, 70's, 80's and 90's |
| 40% | ILLBETHERE | 10 | Words after "Reach Out" in a #1 Four Tops hit |
| 39% | BERNADETTE | 10 | Title woman in a 1967 hit single by the Four Tops |
| 39% | KATEBUSH | 8 | Her "Running Up That Hill (A Deal With God)" became a Billboard Top Ten hit in 2022, decades after its release |
| 39% | DONMCLEAN | 9 | Singer who had a hit with American Pie in 1971 |
| 39% | TONIBASIL | 9 | Singer who had a global hit with Mickey in 1981 |
| 38% | EDWIN | 5 | Singer Starr who had a #1 hit in 1970 with "War" |
| 38% | WESTWING | 8 | Emmy-winning drama four years in a row, with "The" |
| 38% | CHER | 4 | Star who had at least one Billboard Top Ten hit in every decade from the sixties to the nineties |
| 38% | CATBURNS | 8 | British singer who had a hit with Go in 2022 |
| 37% | HALSEY | 6 | Singer/songwriter who had a #5 hit in 2017 with "Bad at Love" |
| 37% | GARYNUMAN | 9 | Synth-pop singer who had a hit with Cars in 1979 |
| 37% | TAYLOR | 6 | With 48-Across, singer who had a #1 hit in 2015 with "Bad Blood" |
| 37% | PAULA | 5 | With 35-Across, singer who had a #1 hit in 1991 with "Rush Rush" |
| 36% | DIDO | 4 | One-named singer who had a big hit with "Thank You" in 2001 |
| 36% | ONFIRE | 6 | Hitting four homers in a game, say |
| 36% | SZA | 3 | Singer with the 2021 top-ten hit "Good Days" |
| 36% | RODSTEWART | 10 | British singer/songwriter who had a Top 20 hit with his version of "Forever Young" in 1988 (2 wds.) |
| 36% | BADHABITS | 9 | Top Ten hit for Ed Sheeran in 2021 |
| 35% | BREAKINGRANKS | 13 | Splitting with one's group ... or a hint to the theme found in four puzzle rows |
| 35% | ARIANA | 6 | With 35-Across, "Problem" singer featured on three songs in Billboard's top 10 during a week in 2014 |
| 35% | CHEESE | 6 | With 58-Across, savory base for a canapé ... and the function of a black square in four puzzle rows? |
| 35% | ONEMISSISSIPPI | 14 | 2021 Kane Brown song with a state in its name that hit the top 40: 2 wds. |
| 34% | EIGHTAMBLUE | 11 | Color that was also a Top Ten hit for Lou Gramm in 1987 |
| 34% | NERD | 4 | Do 10 crosswords in a row, say, with "out" |