| 100% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 59% | GLOVE | 5 | Gold ___ (fielding award won by 14-Across in 2002 and 2003) |
| 49% | SILVERSLUGGER | 13 | Batting award won four times by 17-Across and once by 39-Across: 2 wds. |
| 44% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 44% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 43% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 43% | TIMDUNCAN | 9 | Spurs forward who won the NBA Most Valuable Player award in 2002 and 2003: 2 wds. |
| 41% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 41% | SILVERSLUGGER | 13 | Hitting award won five times by 15-Across, including in 2013: 2 wds. |
| 40% | CYYOUNGAWARD | 12 | Pitching prize won by 30-Across in 1997, 1999, and 2000: 3 wds. |
| 39% | PULITZERPRIZE | 13 | Prestigious award won in 2018 by "DAMN.": 2 wds. |
| 37% | READERSDIGEST | 13 | General interest magazine co-founded by 14-Across and his wife Lila in 1922 (2 wds.) |
| 37% | CENTURYCYCLE | 12 | Series of 10 plays by 14-Across, including "Fences" and "The Piano Lesson," that chronicle life in Black America over a 100-year span: 2 wds. |
| 36% | BLACKSABBATH | 12 | "Iron Man" band cofounded by 14-Across in 1968: 2 wds. |
| 36% | RACHELCARSON | 12 | "Silent Spring" writer and namesake of the international environmental award won by 32-Across in 2019 (2 wds.) |
| 35% | RALPHELLISON | 12 | 14-Across and 28-Across novelist who was awarded the National Medal of Arts in 1985 (2 wds.) |
| 35% | PULITZERPRIZE | 13 | Award won by 18-Across (2 wds.) |
| 34% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |
| 34% | RALPHELLISON | 12 | African-American writer of 14-Across and 28-Across awarded the National Medal of Arts in 1985 (2 wds.) |
| 34% | SHERYLSWOOPES | 13 | Former Houston Comets player who was named the WNBA MVP in 2000, 2002, and 2005: 2 wds. |
| 34% | MVP | 3 | Award won by Breanna Stewart in 2018 and 2023 |
| 34% | STONY | 5 | ___ Award, won in 2002 and 2012 by Snoop Dogg and awarded by "High Times" magazine |
| 34% | SEANPENN | 8 | Two time Academy Award winning actor of "Mystic River" who appeared in a guest role on "Two and a Half Men": 2 wds. |
| 33% | OSCAR | 5 | Award won by Frances McDormand in 2021 (and 2018 and 1997) |
| 33% | MVP | 3 | Award won by 52-Across in 1949 |
| 33% | PULITZERPRIZE | 13 | Award that 14-Across won twice, for "Fences" and "The Piano Lesson": 2 wds. |
| 33% | EMMY | 4 | Award won by 68 Across Rickman for "Rasputin" (is there an echo in here?) |
| 32% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 32% | MOUNTEVEREST | 12 | Peak whose summit was first reached by 14-Across and 39-Across (2 wds.) |
| 32% | EMMY | 4 | Award won multiple times by "Modern Family" and "All in the Family" |