| 100% | TONYAWARD | 9 | Honor that 33-/35-Across won in ten categories, including Best Musical: 2 wds. |
| 41% | ESPYAWARD | 9 | Honor that 33-Across will receive for courage: 2 wds. |
| 36% | WEAREINLOVE | 11 | 33-Across album that won a Grammy for Best Jazz Vocal Performance, Male (4 wds.) |
| 35% | THEFATHER | 9 | 2020 Anthony Hopkins movie that won two Oscars, including Best Actor: 2 wds. |
| 35% | GWENVERDON | 10 | Actress and dancer who won four Tony Awards, including Best Leading Actress in a Musical for "Damn Yankees" (2 wds.) |
| 35% | MARYMARTIN | 10 | Actress and singer who won four Tony Awards, including Best Leading Actress in a Musical for "Peter Pan" (2 wds.) |
| 35% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 35% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 34% | IHOPEYOUDANCE | 13 | Song by 29-Across/32-Across that won the Best Country Song Grammy Award in 2001 (4 wds.) |
| 34% | THEHURTLOCKER | 13 | Iraq War film that won six Oscars in 2009, including Best Picture (3 wds.) |
| 33% | DAMNYANKEES | 11 | "Whatever Lola Wants" show that won the 1956 Tony for Best Musical (2 wds.) |
| 33% | LETITGO | 7 | "Frozen" song that won an Oscar for Best Original Song in 2014 (3 wds.) |
| 33% | MENATWORK | 9 | 15-Across and 33-Across rock band from Australia that won Best New Artist at the 1983 Grammy Awards (3 wds.) |
| 32% | GWENVERDON | 10 | She won three Tony Awards for Best Actress in a Musical, for "Damn Yankees," "New Girl in Town," and "Redhead": 2 wds. |
| 32% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 32% | MARYMARTIN | 10 | She won three Tony Awards for Best Actress in a Musical, for "South Pacific," "Peter Pan," and "The Sound of Music": 2 wds. |
| 32% | THEOPEN | 7 | Major golf tournament that 30-Across won in Scotland in 2013: 2 wds. |
| 32% | LOOKBOTHWAYS | 12 | 29-Across novel subtitled "A Tale Told in Ten Blocks" that won the Carnegie Medal in 2021 (3 wds.) |
| 31% | NEWKIDINTOWN | 12 | 1976 Eagles song that won the Best Arrangement for Voices Grammy in 1977: 4 wds. |
| 31% | THEDEPARTED | 11 | Martin Scorsese film that won the Oscar for Best Picture in 2007 (2 wds.) |
| 31% | PEOPLESCHOICE | 13 | Award 18-Across won in January 2016 as Favorite Breakout Artist: 2 wds. |
| 31% | CITYOFSTARS | 11 | "La La Land" song that won an Oscar for Best Original Song in 2017 (3 wds.) |
| 31% | AMYWINEHOUSE | 12 | British singer who won five Grammys in 2008, including Best New Artist, and died of alcohol poisoning in 2011: 2 wds. |
| 30% | FIGHTFORYOU | 11 | "Judas and the Black Messiah" song that won an Oscar for Best Original Song in 2021 (3 wds.) |
| 30% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 30% | SPINGARNMEDAL | 13 | NAACP award that John Lewis won in 2002: 2 wds. |
| 30% | THEFOGOFWAR | 11 | Documentary film based on Robert S. McNamara that won the Oscar for Best Documentary Feature in 2003: 4 wds. |
| 30% | INABETTERWORLD | 14 | 2010 Danish thriller set in Denmark and Sudan that won an Oscar for Best Foreign Language Film (4 wds.) |
| 30% | MEGHANTRAINOR | 13 | "All About That Bass" singer who won a Best New Artist Grammy in 2016: 2 wds. |
| 30% | PAKSERI | 7 | South Korean golfer who won the women's 35-Across in 1998 (2 wds.) |