| 100% | DAVIDBOWIE | 10 | Singer of 18-Across, 27-Across, and 35-Across (January 8, 1947-January 10, 2016) (2 wds.) |
| 47% | CLINTBLACK | 10 | 18-Across, 26-Across, and 35-Across country singer who won four 1989 Academy of Country Music Awards, including Top Male Vocalist (2 wds.) |
| 45% | JUSTINBIEBER | 12 | Singer of 18-Across and 32-Across who turns 25 years old on March 1 (2 wds.) |
| 44% | DONDELILLO | 10 | Author of "Libra" and "Mao II" who wrote 18-, 26-, and 35-Across: 2 wds. |
| 43% | ALICIAKEYS | 10 | 18-Across and 31-Across singer-songwriter who was born January 25, 1981 (2 wds.) |
| 43% | PAULMCCARTNEY | 13 | 15-Across, 27-Across, and 36-Across singer/songwriter born June 18, 1942 (2 wds.) |
| 43% | BOBBYBROWN | 10 | Former member of 18-Across and singer of 30-Across who turns 50 years old today (2 wds.) |
| 42% | BRUNOMARS | 9 | Singer of 15-Across and 29-Across who was born October 8, 1985 (2 wds.) |
| 42% | MILLERPARK | 10 | Home stadium of the Milwaukee Brewers with statues honoring 18-Across, 26-Across, and 35-Across (2 wds.) |
| 42% | BLUEJEANS | 9 | Casual pants (brands of which can be found at the starts of 16-Across, 27-Across, and 35-Across) (2 wds.) |
| 41% | JASONALDEAN | 11 | "Burnin' It Down" singer who won Entertainer of the Year at the 2016, 2017, and 2018 ACM Awards: 2 wds. |
| 40% | DIERKSBENTLEY | 13 | Singer of "Home" and 15-Across: 2 wds. |
| 40% | ROUNDTABLE | 10 | Meeting place of 18-Across and his knights: 2 wds. |
| 40% | PATTONOSWALT | 12 | Comedian/actor of 14-Across and 29-Across who turned 50 on January 27, 2019 (2 wds.) |
| 39% | LETSGROOVE | 10 | Top 20 song by the band whose name includes the first words of the answers to 18-Across, 26-Across, and 35-Across (2 wds.) |
| 38% | BEBEREXHA | 9 | Singer who performed on 15-, 27-, and 34-Across: 2 wds. |
| 38% | STEPHENKING | 11 | Author of "The Shining" and 18-Across: 2 wds. |
| 38% | FAYEKELLERMAN | 13 | "The Quality of Mercy" novelist who has written 27 mysteries featuring 18-Across and 40-Across (2 wds.) |
| 38% | DIONNEWARWICK | 13 | Singer of many Burt Bacharach songs, including 34- and 44-Across: 2 wds. |
| 37% | BEARBRYANT | 10 | Legendary football coach who won six national championships with the University of Alabama (including one with 18-Across and one with 35-Across) (2 wds.) |
| 37% | SHELLEYFABARES | 14 | Actress and singer who's the niece of 19-Across: 2 wds. |
| 37% | VICKILAWRENCE | 13 | Costar of 39-Across and singer of "The Night the Lights Went Out in Georgia": 2 wds. |
| 37% | LARRYDAVID | 10 | Brooklyn-born comedian who was an executive producer of 27-Across and 32/38-Across: 2 wds. |
| 37% | GORDONSUMNER | 12 | 18-Across and 25-Across singer nicknamed "Sting" because of the black and yellow striped sweater he wore as a young performer (2 wds.) |
| 37% | PEOPLESCHOICE | 13 | Award 18-Across won in January 2016 as Favorite Breakout Artist: 2 wds. |
| 37% | LUKECOMBS | 9 | Country singer whose cover of 27-Across's "Fast Car" was a #2 hit in 2023: 2 wds. |
| 37% | ANNETTEBENING | 13 | Actress and wife of 18-Across, who also appears in "Rules Don't Apply": 2 wds. |
| 36% | POSTMALONE | 10 | 18-Across, 27-Across, and 34-Across rapper/singer who won the 2025 American Music Award for Favorite Country Male Artist (2 wds.) |
| 36% | CORNELIAFUNKE | 13 | Novelist of 18-Across and the "Inkheart" trilogy (2 wds.) |
| 36% | CHRISCORNELL | 12 | Late lead singer of 29-Across and Audioslave (2 wds.) |