| 100% | JASPERJOHNS | 11 | "Three Flags" painter who received the National Medal of Arts in 1990: 2 wds. |
| 79% | ANDREWWYETH | 11 | "Christina's World" painter who received the National Medal of Arts in 2007: 2 wds. |
| 72% | BEVERLYSILLS | 12 | Opera singer who chaired Lincoln Center and received the National Medal of Arts in 1990: 2 wds. |
| 66% | CHUCK | 5 | With 33-Across, "Big Self-Portrait" painter who received the National Medal of Arts in 2000 |
| 60% | MARILYNHORNE | 12 | Opera singer who performed at Clinton's 1993 inauguration and received the National Medal of Arts in 1992: 2 wds. |
| 56% | 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. |
| 55% | TONIMORRISON | 12 | "Beloved" author who received the American Academy of Arts and Letters Gold Medal in 2019: 2 wds. |
| 53% | JOHNUPDIKE | 10 | "Rabbit, Run" author who received the American Academy of Arts and Letters Gold Medal in 2007: 2 wds. |
| 53% | DIANENASH | 9 | Civil rights activist who received the Presidential Medal of Freedom in 2022: 2 wds. |
| 53% | BILLRUSSELL | 11 | Longtime Boston Celtic who received the Presidential Medal of Freedom in 2011: 2 wds. |
| 52% | BARACKOBAMA | 11 | U.S. President who awarded Rita Moreno the National Medal of Arts in 2009 (2 wds.) |
| 52% | OLLIE | 5 | Disney animator Johnston who received the National Medal of Arts |
| 51% | WILLIEMAYS | 10 | Giants Hall of Famer who received the Presidential Medal of Freedom in 2015: 2 wds. |
| 51% | FRANKROBINSON | 13 | Orioles Hall of Famer who received the Presidential Medal of Freedom in 2005: 2 wds. |
| 51% | ERNIEBANKS | 10 | Cubs Hall of Famer who received the Presidential Medal of Freedom in 2013: 2 wds. |
| 51% | MEGANRAPINOE | 12 | Olympic champion soccer player who received the Presidential Medal of Freedom in 2022: 2 wds. |
| 51% | ROGERSTAUBACH | 13 | Longtime Dallas Cowboys quarterback who received the Presidential Medal of Freedom in 2018: 2 wds. |
| 50% | STEVEJOBS | 9 | Cofounder of Apple who received the Presidential Medal of Freedom posthumously in 2022: 2 wds. |
| 49% | RALPHELLISON | 12 | 14-Across and 28-Across novelist who was awarded the National Medal of Arts in 1985 (2 wds.) |
| 49% | KIRKDOUGLAS | 11 | "Spartacus" actor who received the French Legion of Honor medal in 1985: 2 wds. |
| 49% | ELDOCTOROW | 10 | "Ragtime" author who received the American Academy of Arts and Letters Gold Medal in 2013: 3 wds. |
| 48% | IRVINGBERLIN | 12 | Composer of the song "White Christmas" who received the Presidential Medal of Freedom in 1977: 2 wds. |
| 48% | AARONCOPLAND | 12 | Composer of the ballet "Appalachian Spring" who received the Presidential Medal of Freedom in 1964: 2 wds. |
| 47% | DUKEELLINGTON | 13 | Composer of the jazz classic "Mood Indigo" who received the Presidential Medal of Freedom in 1969: 2 wds. |
| 47% | MARTINSCORSESE | 14 | "Raging Bull" director who received the French Legion of Honor medal in 2005: 2 wds. |
| 45% | DALAILAMA | 9 | Tibet's spiritual leader who received the Congressional Gold Medal in 2006: 2 wds. |
| 45% | NELSONMANDELA | 13 | Former South African president who received the Congressional Gold Medal in 1998: 2 wds. |
| 45% | TONYBLAIR | 9 | Former British prime minister who received the Congressional Gold Medal in 2003: 2 wds. |
| 45% | ODETTA | 6 | Singer awarded the National Medal of Arts in 1999 |
| 45% | QUINCYJONES | 11 | "We Are the World" producer who received the French Legion of Honor medal in 2001: 2 wds. |