| 100% | RALPHELLISON | 12 | African-American writer of 14-Across and 28-Across awarded the National Medal of Arts in 1985 (2 wds.) |
| 74% | RALPHELLISON | 12 | 14-Across and 28-Across novelist who was awarded the National Medal of Arts in 1985 (2 wds.) |
| 56% | BEVERLYSILLS | 12 | Opera singer who chaired Lincoln Center and received the National Medal of Arts in 1990: 2 wds. |
| 55% | MARILYNHORNE | 12 | Opera singer who performed at Clinton's 1993 inauguration and received the National Medal of Arts in 1992: 2 wds. |
| 54% | BARACKOBAMA | 11 | U.S. President who awarded Rita Moreno the National Medal of Arts in 2009 (2 wds.) |
| 51% | JASPERJOHNS | 11 | "Three Flags" painter who received the National Medal of Arts in 1990: 2 wds. |
| 51% | ANDREWWYETH | 11 | "Christina's World" painter who received the National Medal of Arts in 2007: 2 wds. |
| 49% | RUBYDEE | 7 | Actress and activist who was awarded the National Medal of Arts, along with her husband, in 1995 |
| 49% | TONIMORRISON | 12 | "Beloved" author who received the American Academy of Arts and Letters Gold Medal in 2019: 2 wds. |
| 49% | JOHNUPDIKE | 10 | "Rabbit, Run" author who received the American Academy of Arts and Letters Gold Medal in 2007: 2 wds. |
| 47% | ODETTA | 6 | Singer awarded the National Medal of Arts in 1999 |
| 47% | TONYKUSHNER | 11 | "Angels in America" Pulitzer winner and 2005 inductee into the American Academy of Arts and Letters: 2 wds. |
| 47% | 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. |
| 47% | TANEHISICOATES | 14 | African-American author of "Between the World and Me," winner of the 2015 National Book Award for Nonfiction: 2 wds. |
| 45% | VITOCORLEONE | 12 | Mafia don played by both 14-Across and 28-Across in the "Godfather" franchise: 2 wds. |
| 45% | JIMTHORPE | 9 | Native American Olympic gold medalist and NFL All-Pro posthumously awarded the Presidential Medal of Freedom by Joe Biden: 2 wds. |
| 44% | RACHELCARSON | 12 | "Silent Spring" writer and namesake of the international environmental award won by 32-Across in 2019 (2 wds.) |
| 44% | ITZHAKPERLMAN | 13 | Tel Aviv-born violinist who was awarded the Presidential Medal of Freedom in 2015: 2 wds. |
| 43% | SOLANGEKNOWLES | 14 | 12-Across and 28-Across singer who was the first recipient of the "Billboard" Women in Music Impact Award (2 wds.) |
| 43% | JAMESMCBRIDE | 12 | African-American author of "The Good Lord Bird," winner of the 2013 National Book Award for Fiction: 2 wds. |
| 43% | ELDOCTOROW | 10 | "Ragtime" author who received the American Academy of Arts and Letters Gold Medal in 2013: 3 wds. |
| 43% | ISABELALLENDE | 13 | Chilean-American writer who was awarded the 2014 Presidential Medal of Freedom: 2 wds. |
| 42% | JEANKING | 8 | Billie ___, former World No. 1 professional tennis player who was awarded the Presidential Medal of Freedom in 2009: 2 wds. |
| 42% | TONIMORRISON | 12 | "Beloved" Pulitzer winner and 1981 inductee into the American Academy of Arts and Letters: 2 wds. |
| 42% | REGGIEMILLER | 12 | Shaquille and ___ were the only two players in both the gold medal-winning national teams of 1994 and 1996: 2 wds. |
| 42% | CUBAGOODING | 11 | Academy Award-winning actor from "Jerry Maguire", who plays the TV version of 14-Across in "American Crime Story" : 2 wds. |
| 42% | ANNIEPROULX | 11 | "The Shipping News" Pulitzer winner and 2007 inductee into the American Academy of Arts and Letters: 2 wds. |
| 42% | RALPHELLISON | 12 | African-American author of "Invisible Man," winner of the 1953 National Book Award for Fiction: 2 wds. |
| 42% | GABRIELLEZEVIN | 14 | 16-Across and 28-Across writer whose novel "Tomorrow, and Tomorrow, and Tomorrow" won the Goodreads Choice Award Winner for Best Fiction in 2022 (2 wds.) |
| 42% | ALLYSONFELIX | 12 | American track and field sprinter who won the 2012 Olympic gold in 200 meters and has a total of 9 Olympic medals: 2 wds. |