| 100% | HERMANWOUK | 10 | "The Caine Mutiny," 18-Across, and 31-Across novelist who passed away at age 103 on May 17, 2019 (2 wds.) |
| 41% | TONYBENNETT | 11 | 17-Across and 30-Across collaborator who passed away on July 21, 2023 (2 wds.) |
| 40% | EDDIEMONEY | 10 | "Two Tickets to Paradise," 18-Across, and 33-Across singer who passed away September 13, 2019 (2 wds.) |
| 40% | HARRYBELAFONTE | 14 | "Day-O" singer/actor/activist who passed away on April 25, 2023, at the age of 96 (2 wds.) |
| 40% | JOHNSINGLETON | 13 | Director of 18-Across and 40-Across who passed away in 2019 (2 wds.) |
| 39% | COLLEENHOOVER | 13 | 19-Across and 31-Across novelist who surged in popularity in the #BookTok community on TikTok in 2021 (2 wds.) |
| 36% | BILLIEEILISH | 12 | "Bad Guy," 17-Across, and 42-Across singer who won Best New Artist at the 2019 MTV Video Music Awards (2 wds.) |
| 36% | FATSDOMINO | 10 | Legendary singer of 31-Across, "Ain't That a Shame," and "Walking to 17-Across," who passed away October 24, 2017 (2 wds.) |
| 36% | IANMCEWAN | 9 | 15-Across and 31-Across novelist who turns 75 on June 21, 2023 (2 wds.) |
| 36% | MARYSHELLEY | 11 | Author who began writing 28-Across at the age of 18: 2 wds. |
| 35% | TONIMORRISON | 12 | 18-Across and 32-Across novelist who won the 1993 Nobel Prize for Literature (2 wds.) |
| 35% | SHAWNCARTER | 11 | 18-Across and 29-Across rapper who turns 50 on December 4, 2019 (2 wds.) |
| 35% | RUDYARDKIPLING | 14 | English author who wrote the children's literature at 18- and 41-Across: 2 wds. |
| 35% | SELENAGOMEZ | 11 | 18-Across and 30-Across singer who plays Mabel Mora on "Only Murders in the Building" (2 wds.) |
| 35% | CYNTHIANIXON | 12 | "Sex and the City" actress who plays struggling socialite Ada Brook on 17-Across: 2 wds. |
| 35% | PEI | 3 | I.M. ___, Pritzker Prize-winning architect behind the Louvre in Paris who passed away at the age of 102 in 2019 |
| 34% | ANGIETHOMAS | 11 | Novelist who wrote the Y.A. bestsellers 17-Across and 29-Across (2 wds.) |
| 33% | CHLOEKIM | 8 | American snowboarder who won an Olympic gold medal at the age of 17: 2 wds. |
| 33% | LITTLEWOMEN | 11 | 2019 Greta Gerwig film starring Emma Watson, 17-Across, and 28-Across based on a Louisa May Alcott novel (2 wds.) |
| 33% | HENRYCAVILL | 11 | 18-Across, 24-Across, and 33-Across star who was born on May 5, 1983 (2 wds.) |
| 33% | CAROLCHANNING | 13 | Singer/actress who passed away on January 15, 2019 (2 wds.) |
| 32% | LEIGHBARDUGO | 12 | American novelist who wrote 17-Across, 40-Across, and the "Shadow and Bone" trilogy (2 wds.) |
| 32% | ANDREWLUCK | 10 | Four-time Pro Bowl quarterback who retired in 2019 at the age of 29: 2 wds. |
| 32% | HARLANCOBEN | 11 | 17-Across and 30-Across novelist who is the first writer to win an Anthony Award, a Shamus Award, and an Edgar Award (2 wds.) |
| 32% | CLINTEASTWOOD | 13 | Actor and director who turns 90 on May 31, 2020 (2 wds.) |
| 32% | HARRYSHOUSE | 11 | 2022 album featuring 17-Across, 23-Across, and 33-Across that debuted at No. 1 on the "Billboard" 200 (2 wds.) |
| 32% | GILLIANFLYNN | 12 | Author who wrote the novels from which 17-Across and 29-/31-Across were adapted: 2 wds. |
| 32% | TORIKELLY | 9 | "Nobody Love" singer who first started posting videos on YouTube at the age of 14: 2 wds. |
| 32% | RICOCASEK | 9 | Lead singer of The Cars who passed away September 15, 2019 (2 wds.) |
| 32% | THOMASRHETT | 11 | 17-Across and 28-Across singer who was the 2019 Academy of Country Music's Male Artist of the Year (2 wds.) |