| 100% | DONPARDO | 8 | Announcer on 5-Across and 48-Across who died on August 18, 2014: 2 wds. |
| 54% | JERRYLEWIS | 10 | Comedian and humanitarian who died on August 20: 2 wds. |
| 47% | HENRYCAVILL | 11 | 18-Across, 24-Across, and 33-Across star who was born on May 5, 1983 (2 wds.) |
| 47% | CHUCKBERRY | 10 | Rock-and-roll legend and singer of "Roll Over Beethoven," who died on 3/18/17: 2 wds. |
| 45% | MAYAANGELOU | 11 | Poet/memoirist who died on 5/28/14: 2 wds. |
| 45% | KURTWARNER | 10 | Rams and Cardinals quarterback who will be inducted into the Pro Football Hall of Fame on August 5: 2 wds. |
| 45% | TONIMORRISON | 12 | "Beloved" author who died August 5, and who was the first African-American woman to win a Nobel Prize: 2 wds. |
| 44% | SAMSHEPARD | 10 | "True West" playwright and "The Right Stuff" actor who died on July 27: 2 wds. |
| 44% | KOBEBRYANT | 10 | 18-time All-Star for the LA Lakers who died on 1/26/20: 2 wds. |
| 44% | DENNISLEHANE | 12 | Writer of "Mystic River," 18-Across, and 32-Across who was born August 4, 1965 (2 wds.) |
| 42% | BEVERLYCLEARY | 13 | Children's author of 18-Across and 30-Across who turned 102 on April 12 (2 wds.) |
| 42% | SHAWNCARTER | 11 | 18-Across and 29-Across rapper who turns 50 on December 4, 2019 (2 wds.) |
| 41% | JOHNNYGILBERT | 13 | Announcer on 48-Across since 1984: 2 wds. |
| 40% | JERRYJONES | 10 | Cowboys owner who will be inducted into the Pro Football Hall of Fame on August 5: 2 wds. |
| 40% | BURTREYNOLDS | 12 | "Smokey and the Bandit" star who died 9/6/18: 2 wds. |
| 40% | GRACIEABRAMS | 12 | 18-Across and 32-Across singer-songwriter who often opens for Taylor Swift on her Eras Tour (2 wds.) |
| 40% | JUSTINBIEBER | 12 | Singer of 18-Across and 32-Across who turns 25 years old on March 1 (2 wds.) |
| 40% | SELENAGOMEZ | 11 | 18-Across and 30-Across singer who plays Mabel Mora on "Only Murders in the Building" (2 wds.) |
| 39% | RITAMORENO | 10 | Emmy, Grammy, Oscar, and Tony winner who stars on 32-Across: 2 wds. |
| 39% | GEORGEMICHAEL | 13 | Singer who died on 12/25/16: 2 wds. |
| 38% | TILDASWINTON | 12 | 18-Across and 30-Across co-star who co-stars with Bill Murray in "The Dead Don't Die" (2 wds.) |
| 38% | DEBBIEGIBSON | 12 | "Electric Youth" singer who sings "Heartbreak Holiday" with 18-Across and "White Christmas" with her father on 30-Across (2 wds.) |
| 38% | CURTISMAYFIELD | 14 | Group member who wrote and sang 48-Across: 2 wds. |
| 38% | HARRYANDERSON | 13 | Actor who played Judge Stone on 18-Across: 2 wds. |
| 38% | GERALDMCRANEY | 13 | "Major Dad" actor who costars on 18-Across: 2 wds. |
| 38% | JOANRIVERS | 10 | Pioneering comedian who died on 9/4/14: 2 wds. |
| 38% | ADAMWEST | 8 | 1960s Batman portrayer who died on June 9: 2 wds. |
| 38% | LYNDACARTER | 11 | Actress who portrayed 17- and 25-Across on TV from 1975 to 1979: 2 wds. |
| 38% | DICKENBERG | 10 | Hall of Fame sportscaster who died on December 21: 2 wds. |
| 38% | EARLWEAVER | 10 | Legendary Baltimore manager who died on 1/19/2013: 2 wds. |