| 100% | CHUCK | 5 | With 33-Across, "Big Self-Portrait" painter who received the National Medal of Arts in 2000 |
| 64% | JASPERJOHNS | 11 | "Three Flags" painter who received the National Medal of Arts in 1990: 2 wds. |
| 64% | ANDREWWYETH | 11 | "Christina's World" painter who received the National Medal of Arts in 2007: 2 wds. |
| 50% | OLLIE | 5 | Disney animator Johnston who received the National Medal of Arts |
| 48% | BEVERLYSILLS | 12 | Opera singer who chaired Lincoln Center and received the National Medal of Arts in 1990: 2 wds. |
| 45% | RUBYDEE | 7 | Actress and activist who was awarded the National Medal of Arts, along with her husband, in 1995 |
| 44% | MARILYNHORNE | 12 | Opera singer who performed at Clinton's 1993 inauguration and received the National Medal of Arts in 1992: 2 wds. |
| 43% | ODETTA | 6 | Singer awarded the National Medal of Arts in 1999 |
| 42% | ERNIE | 5 | With 35-Across, baseball player who received the Presidential Medal of Freedom in 2013 and died 1/23/15 |
| 41% | TONIMORRISON | 12 | "Beloved" author who received the American Academy of Arts and Letters Gold Medal in 2019: 2 wds. |
| 41% | ELDOCTOROW | 10 | "Ragtime" author who received the American Academy of Arts and Letters Gold Medal in 2013: 3 wds. |
| 40% | RENEEFLEMING | 12 | Opera singer who sang the national anthem at the Super Bowl in 2014 and received the National Medal of Arts in 2012: 2 wds. |
| 40% | BARACKOBAMA | 11 | U.S. President who awarded Rita Moreno the National Medal of Arts in 2009 (2 wds.) |
| 40% | RALPHELLISON | 12 | 14-Across and 28-Across novelist who was awarded the National Medal of Arts in 1985 (2 wds.) |
| 39% | JOHNUPDIKE | 10 | "Rabbit, Run" author who received the American Academy of Arts and Letters Gold Medal in 2007: 2 wds. |
| 39% | CHRIS | 5 | With 33-Across, "Guardians of the Galaxy" star who plays Owen Grady in 15-/49-Across |
| 38% | PEARL | 5 | Singer Bailey who received the Presidential Medal of Freedom in '88 |
| 38% | TRUMAN | 6 | With 33-Across, friend of 15-Across who was the basis for Dill in "To Kill a Mockingbird" |
| 37% | ALPERT | 6 | Herb honored with a National Medal of Arts in 2013 |
| 37% | DIANENASH | 9 | Civil rights activist who received the Presidential Medal of Freedom in 2022: 2 wds. |
| 37% | BILLRUSSELL | 11 | Longtime Boston Celtic who received the Presidential Medal of Freedom in 2011: 2 wds. |
| 36% | OPRAHWINFREY | 12 | TV talk show host who received the NAACP's Spingarn Medal in 2000: 2 wds. |
| 36% | AILEY | 5 | Choreographer who posthumously received the Presidential Medal of Freedom in 2014 |
| 36% | MARGOT | 6 | With 33-Across, "The Wolf of Wall Street" actress who played Harley Quinn in "Suicide Squad" |
| 36% | WILLIEMAYS | 10 | Giants Hall of Famer who received the Presidential Medal of Freedom in 2015: 2 wds. |
| 36% | FRANKROBINSON | 13 | Orioles Hall of Famer who received the Presidential Medal of Freedom in 2005: 2 wds. |
| 36% | ERNIEBANKS | 10 | Cubs Hall of Famer who received the Presidential Medal of Freedom in 2013: 2 wds. |
| 36% | STEVEJOBS | 9 | Cofounder of Apple who received the Presidential Medal of Freedom posthumously in 2022: 2 wds. |
| 35% | MEGANRAPINOE | 12 | Olympic champion soccer player who received the Presidential Medal of Freedom in 2022: 2 wds. |
| 35% | ROGERSTAUBACH | 13 | Longtime Dallas Cowboys quarterback who received the Presidential Medal of Freedom in 2018: 2 wds. |