| 100% | DORIS | 5 | "Que Será, Será" singer Day who passed away on May 13, 2019 |
| 57% | CAROLCHANNING | 13 | Singer/actress who passed away on January 15, 2019 (2 wds.) |
| 55% | BART | 4 | Football Hall of Fame quarterback Starr who passed away on May 26, 2019 |
| 49% | EDDIEMONEY | 10 | "Two Tickets to Paradise," 18-Across, and 33-Across singer who passed away September 13, 2019 (2 wds.) |
| 46% | HERMANWOUK | 10 | "The Caine Mutiny," 18-Across, and 31-Across novelist who passed away at age 103 on May 17, 2019 (2 wds.) |
| 46% | HARRYBELAFONTE | 14 | "Day-O" singer/actor/activist who passed away on April 25, 2023, at the age of 96 (2 wds.) |
| 43% | STEVIEWONDER | 12 | "Songs in the Key of Life" singer-songwriter who was born on May 13, 1950 (2 wds.) |
| 43% | RICOCASEK | 9 | Lead singer of The Cars who passed away September 15, 2019 (2 wds.) |
| 39% | DORIS | 5 | ___ Day, Presidential Medal of Freedom honoree and actress from "The Man Who Knew Too Much" who passed away in 2019 |
| 36% | TOMSEAVER | 9 | Pitching legend and World Series champion who passed away on Aug. 31 |
| 36% | TYLERPERRY | 10 | Entertainer who turns 50 on September 13, 2019 (2 wds.) |
| 35% | STEPHENHAWKING | 14 | Scientist who notably passed away on 33-Down (2018) |
| 35% | DORIS | 5 | "Que Sera, Sera" singer ___ Day |
| 35% | TONYBENNETT | 11 | 17-Across and 30-Across collaborator who passed away on July 21, 2023 (2 wds.) |
| 34% | TONIMORRISON | 12 | 1993 Nobel Laureate in Literature who passed away August 5, 2019 (2 wds.) |
| 34% | CLEO | 4 | ___ Laine, famed British jazz singer who passed away in July 2025 |
| 34% | SUZI | 4 | Singer Quatro who played Leather Tuscadero on Happy Days |
| 34% | LORETTALYNN | 11 | Country Music Hall of Fame singer-songwriter who passed away in 2022 (2 wds.) |
| 34% | ENGEL | 5 | "The Mary Tyler Moore Show" actress Georgia who passed away in 2019 |
| 34% | PATTI | 5 | Singer LaBelle who competed on "The Masked Singer" in 2019 |
| 33% | JOHNSINGLETON | 13 | Director of 18-Across and 40-Across who passed away in 2019 (2 wds.) |
| 33% | JIMMYBUFFETT | 12 | Lead singer for the Coral Reefer Band who passed away in 2023 (2 wds.) |
| 33% | GEORGIA | 7 | ___ Engel, Emmy-winning actress from "The Mary Tyler Moore Show" who passed away in 2019 |
| 32% | MORRISON | 8 | Toni ___, Nobel laureate behind works like "The Bluest Eye" and "Home" who passed away in 2019 |
| 32% | ARCHIE | 6 | ___ Mountbatten-Windsor, Prince Harry and Meghan Markle's son who was born on 6th May 2019 |
| 32% | TIMMCGRAW | 9 | "Just to See You Smile" country singer who turned 50 on May 1, 2017 (2 wds.) |
| 31% | ANA | 3 | Gasteyer who was the Tree on "The Masked Singer" in 2019 |
| 31% | TRAINER | 7 | Someone who might work you hard on leg day |
| 31% | FRANKIEVALLI | 12 | 30-Across singer who turns 90 years old on May 3, 2024 (2 wds.) |
| 31% | ROSALIA | 7 | 2019 international breakout pop singer who draws on her traditional flamenco training |