| 100% | TONYAWARD | 9 | 2005 Broadway honor won by 15-Across: 2 wds. |
| 63% | GOLDMEDAL | 9 | Olympic honor won six times by 15-Across: 2 wds. |
| 55% | HEISMANTROPHY | 13 | Award won by 15-/18-Across in December 2011: 2 wds. |
| 55% | PULITZERPRIZE | 13 | Award won by 15-, 19-, 43-, and 52-Across: 2 wds. |
| 53% | ACADEMYAWARDS | 13 | Golden statuettes won by 15- and 26-/34-Across during a February 22 ceremony: 2 wds. |
| 50% | EMMYAWARD | 9 | Honor won twice by 18-Across in the 1950s for playing Schultzy on "The Bob Cummings Show": 2 wds. |
| 49% | LETSMOVE | 8 | Kids' fitness initiative led by 15-Across: 2 wds. |
| 49% | YOUBABY | 7 | 1966 song and album by 15-Across: 2 wds. |
| 49% | TUTTIFRUTTI | 11 | 1955 song by 15-Across: 2 wds. |
| 49% | RIVERDALEHIGH | 13 | School attended by 15-Across: 2 wds. |
| 49% | JERSEYBOYS | 10 | 2005 Broadway jukebox musical featuring songs by the Four Seasons: 2 wds. |
| 48% | THEWIRE | 7 | 2013 rock song by 15-Across: 2 wds. |
| 48% | SCHOOLSTRIKES | 13 | Teen walkouts inspired by 15-Across: 2 wds. |
| 47% | LARRYFINE | 9 | Bushy-haired Stooge called "Porcupine" by 15-Across: 2 wds. |
| 47% | WORLDCHAMPION | 13 | Title earned by 15-Across eight times: 2 wds. |
| 46% | SILVERSLUGGER | 13 | Hitting award won five times by 15-Across, including in 2013: 2 wds. |
| 45% | SQUEEZEMACHINE | 14 | Calming device, also known as a "hug box," invented by 15-Across: 2 wds. |
| 44% | HARRYCALLAHAN | 13 | Police inspector played by 15-Across in "Sudden Impact": 2 wds. |
| 44% | RATHERLIE | 9 | 2025 hit by 15-Across with Playboi Carti about dishonesty: 2 wds. |
| 43% | VANGOGH | 7 | Dutch artist portrayed by 15-Across, 20-Across, and 34-Across: 2 wds. |
| 43% | TOUCHDOWNPASS | 13 | One of a record 50 thrown by 15-Across in 2007: 2 wds. |
| 43% | PULITZERPRIZE | 13 | Fiction award won by 18-/42-Across in 2015: 2 wds. |
| 43% | ANOSE | 5 | Win by ___ (horseracing term): 2 wds. |
| 43% | HAPPYTOGETHER | 13 | 1967 song by 15-Across that was the group's biggest hit: 2 wds. |
| 42% | PULITZERPRIZE | 13 | Award won by 18-Across (2 wds.) |
| 42% | NEWTSCAMANDER | 13 | Character played by 15-Across in "Fantastic Beasts and Where to Find Them": 2 wds. |
| 42% | BESTACTOR | 9 | Oscar won by 21-Across for "The King's Speech": 2 wds. |
| 42% | KELLYBUNDY | 10 | Ditzy character played by 15-/50-Across on "Married... with Children": 2 wds. |
| 42% | ANOSE | 5 | Win by ___ (win by a narrow margin): 2 wds. |
| 42% | ANOSE | 5 | Win by ___ (barely be victorious): 2 wds. |