| 100% | BLONDEFAITH | 11 | 2007 novel featuring 17-Across for which 29-Across won the NAACP Image Award for Outstanding Literary Work, Fiction (2 wds.) |
| 58% | ASBRAVEASYOU | 12 | 29-Across novel that won the Kirkus Prize in 2016 and the NAACP Image Award for Outstanding Literary Work for Youth/Teen in 2017 (4 wds.) |
| 48% | INVISIBLEMAN | 12 | Novel written by Ralph Waldo Ellison (birthday today) which won the National Book Award for Fiction in 1953: 2 wds. |
| 43% | LUPITANYONGO | 12 | She won the 2020 NAACP Image Award for Outstanding Actress for "Us": 2 wds. |
| 42% | WILLSMITH | 9 | "Ali" actor who won the NAACP Image Award for Entertainer of the Year in 1999: 2 wds. |
| 42% | JAMIEFOXX | 9 | "Ray" actor who won the NAACP Image Award for Entertainer of the Year in 2013: 2 wds. |
| 42% | DWAYNEJOHNSON | 13 | "Hobbs & Shaw" actor who won the NAACP Image Award for Entertainer of the Year in 2017: 2 wds. |
| 42% | MARSAIMARTIN | 12 | She won the 2020 NAACP Award for Outstanding Supporting Actress for "Little": 2 wds. |
| 40% | ALEXBERENSON | 12 | Novelist whose "The Faithful Spy" won the 2007 Edgar Award for Best First Novel (2 wds.) |
| 39% | WILLIAMSTYRON | 13 | Novelist who won the National Book Award for Fiction for 15-Across (2 wds.) |
| 39% | THEECHOMAKER | 12 | 2006 novel by 32-Across that won the National Book Award for Fiction (3 wds.) |
| 39% | 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.) |
| 38% | SUSANCHOI | 9 | 15-Across and 33-Across writer who won the 2019 National Book Award for Fiction for her novel "Trust Exercise" (2 wds.) |
| 38% | OFA | 3 | "Half ___ Yellow Sun," novel by Chimamanda Ngozi Adichie that won the 2007 Orange Prize for Fiction: 2 wds. |
| 38% | MICHAELBJORDAN | 14 | He won the 2020 NAACP Image Award for Outstanding Actor for "Just Mercy": 3 wds. |
| 38% | CHARLESYU | 9 | Writer whose novel "Interior Chinatown" won the 2020 National Book Award for Fiction (2 wds.) |
| 38% | SUSANCHOI | 9 | Writer whose novel "Trust Exercise" won the 2019 National Book Award for Fiction (2 wds.) |
| 38% | THEROUNDHOUSE | 13 | Louise Erdrich novel that won the National Book Award for Fiction in 2012 (3 wds.) |
| 38% | LORDOFMISRULE | 13 | Jaimy Gordon novel that won the National Book Award for Fiction in 2010 (3 wds.) |
| 38% | TESSGUNTY | 9 | Writer whose novel "The Rabbit Hutch" won the 2022 National Book Award for Fiction (2 wds.) |
| 37% | HELLODOLLY | 10 | Broadway show for which 30-Across won the 1964 Tony Award for Best Actress in a Musical (2 wds.) |
| 37% | JASONMOTT | 9 | Writer whose novel "Hell of a Book" won the 2021 National Book Award for Fiction (2 wds.) |
| 37% | LEIGHBARDUGO | 12 | 18-Across and 29-Across writer whose novel "Ninth House" won the 2019 Goodreads Choice Award for Best Fantasy (2 wds.) |
| 37% | POSTCARDS | 9 | Novel by 29-Across that won the 1992 PEN/Faulkner Award for fiction |
| 37% | THEOVERSTORY | 12 | Novel by 30-Across that won the Pulitzer Prize for Fiction (2 wds.) |
| 37% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 36% | NEVERLET | 8 | "___ Me Go," 2005 novel by Kazuo Ishiguro for which he won the ALA Alex Award and which was also adapted into a movie: 2 wds. |
| 36% | JANELLEMONAE | 12 | "Dirty Computer" singer who won the GLAAD Media Award for Outstanding Music Artist in 2019: 2 wds. |
| 36% | SAMSMITH | 8 | "Love Goes" singer who won the GLAAD Media Award for Outstanding Music Artist in 2021: 2 wds. |
| 36% | EUGENELEVY | 10 | Former SCTV regular who won the 2020 Emmy Award for Outstanding Lead Actor in a Comedy Series for playing Johnny Rose on 46-Across (2 wds.) |