| 100% | RACHELCARSON | 12 | "Silent Spring" writer and namesake of the international environmental award won by 32-Across in 2019 (2 wds.) |
| 42% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 39% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 36% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 35% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 35% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 35% | MEGANRAPINOE | 12 | Co-captain of the USWNT who won the Golden Ball award and scored one of the two goals in the team's World Cup final game victory over 17-Across (2 wds.) |
| 35% | COCOCHANEL | 10 | French fashion designer and namesake of the brand that was founded in 1909 and is known for its perfume No. 5: 2 wds. |
| 35% | ROALDDAHL | 9 | Writer of the children's books that the movies directed by 14-, 20-, and 36-Across were based on: 2 wds. |
| 35% | ASHLEIGHBARTY | 13 | Australian tennis player who won WTA Player of the Year in 2019 and 2021: 2 wds. |
| 34% | MIKETROUT | 9 | LA Angel who won the AL MVP award in 2014, 2016, and 2019: 2 wds. |
| 34% | NAOMIOSAKA | 10 | Japanese tennis player who won the Laureus Breakthrough of the Year award in 2019: 2 wds. |
| 34% | NOVAKDJOKOVIC | 13 | Serbian tennis player who won the Laureus Sportsman of the Year award in 2019: 2 wds. |
| 34% | TIGERWOODS | 10 | American professional golfer who won the Laureus Comeback of the Year award in 2019: 2 wds. |
| 34% | CHRISEVERT | 10 | Tennis player who won the AP Athlete of the Year award in 1974, 1975, 1977, and 1980: 2 wds. |
| 34% | SERENAWILLIAMS | 14 | Tennis player who won the AP Athlete of the Year award in 2002, 2009, 2013, and 2015: 2 wds. |
| 34% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 34% | BESTMUSICAL | 11 | Award won by the starts of 17-, 25-, 39- and 52-Across and 11- and 29-Down |
| 34% | ANDYMURRAY | 10 | Scottish tennis player defeated by 32-Across in the 2016 Australian Open finals: 2 wds. |
| 33% | ANYTHINGGOES | 12 | 1934 show with music and lyrics by 39-Across whose 1987 and 2011 revivals both won the Tony Award for Best Revival of a Musical (2 wds.) |
| 33% | BENWALLACE | 10 | Retired Pistons center who won consecutive Defensive Player of the Year Awards twice, in 2003 and 2006: 2 wds. |
| 33% | RUDYGOBERT | 10 | Jazz center who won his second consecutive Defensive Player of the Year Award in 2019: 2 wds. |
| 33% | THEECHOMAKER | 12 | 2006 novel by 32-Across that won the National Book Award for Fiction (3 wds.) |
| 33% | SONGOFTHEYEAR | 13 | One of the two Grammy categories won by 31-Across in 2013: 4 wds. |
| 33% | BESTNEWARTIST | 13 | One of the two Grammy categories won by 31-Across in 2013: 3 wds. |
| 33% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 33% | GRAMMY | 6 | Award won by "DAMN." in the category of Best Rap Album |
| 33% | TIMEMAGAZINE | 12 | Publication that named 18-Across 1963's Woman of the Year in its 100 Women of the Year project and 32-Across 2019's Person of the Year (2 wds.) |
| 33% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 33% | COMICBOOK | 9 | Setting for each of the places in 15-, 21-, and 41-Across: 2 wds. |