| 100% | SILVERSLUGGER | 13 | Hitting award won five times by 15-Across, including in 2013: 2 wds. |
| 52% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 45% | GOLDMEDAL | 9 | Olympic honor won six times by 15-Across: 2 wds. |
| 45% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 44% | SILVERSLUGGER | 13 | Batting award won four times by 17-Across and once by 39-Across: 2 wds. |
| 43% | SILVERSLUGGER | 13 | NL batting award won by 14-Across in 2000, 2002, and 2003: 2 wds. |
| 41% | PULITZERPRIZE | 13 | Prestigious award won in 2018 by "DAMN.": 2 wds. |
| 41% | VIDEOVANGUARD | 13 | Achievement award won by 17-Across in 1987 (it was renamed in 1991 for Michael Jackson): 2 wds. |
| 41% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 39% | WORLDCHAMPION | 13 | Title earned by 15-Across eight times: 2 wds. |
| 38% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 38% | TOUCHDOWNPASS | 13 | One of a record 50 thrown by 15-Across in 2007: 2 wds. |
| 38% | HARRYCALLAHAN | 13 | Police inspector played by 15-Across in "Sudden Impact": 2 wds. |
| 38% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 37% | SIGN | 4 | "___ of the Times," hit song by Harry Styles which won a Brit Award in 2018 |
| 37% | BADBUNNY | 8 | "Dákiti" singer who won five Billboard Music Awards, including Top Latin Artist, in 2021 (2 wds.) |
| 37% | JUSTINBIEBER | 12 | 26-time "Billboard" Music Award winner who had five Top 10 hits in 2020, including 17-Across and 39-Across (2 wds.) |
| 37% | HAPPYTOGETHER | 13 | 1967 song by 15-Across that was the group's biggest hit: 2 wds. |
| 37% | AMYWINEHOUSE | 12 | "Back to Black" singer who won five Grammy Awards in 2008: 2 wds. |
| 37% | ALISONKRAUSS | 12 | "Raising Sand" singer who won five Grammy Awards in 2009: 2 wds. |
| 36% | THEWIRE | 7 | 2013 rock song by 15-Across: 2 wds. |
| 36% | NEWTSCAMANDER | 13 | Character played by 15-Across in "Fantastic Beasts and Where to Find Them": 2 wds. |
| 36% | JAMESMCBRIDE | 12 | 15-Across and 47-Across writer who won the 2013 National Book Award for Fiction for "The Good Lord Bird" (2 wds.) |
| 36% | ROLLING | 7 | "___ in the Deep," hit song by Adele that won 3 Grammy awards including Record of the Year in 2012 |
| 36% | COUNTINGSTARS | 13 | 2013 #2 hit by 43-Across: 2 wds. |
| 36% | PULITZERPRIZE | 13 | Award won by 18-Across (2 wds.) |
| 36% | EMMY | 4 | Award won multiple times by "Modern Family" and "All in the Family" |
| 35% | PULITZERPRIZE | 13 | Award won by 18-Across for "Beloved" (2 wds.) |
| 35% | RATHERLIE | 9 | 2025 hit by 15-Across with Playboi Carti about dishonesty: 2 wds. |
| 35% | PULITZERPRIZE | 13 | Award won by 40-Across for 18-Across (2 wds.) |