| 100% | KISSMEKATE | 10 | 1948 Broadway show, with music and lyrics by 41-Across, that won the first Tony for Best Musical: 3 wds. |
| 85% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 63% | 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.) |
| 52% | SILKSTOCKINGS | 13 | 1955 Broadway show with music and lyrics by 41-Across: 2 wds. |
| 45% | ACHORUSLINE | 11 | "What I Did for Love" show that won the 1976 Tony for Best Musical (3 wds.) |
| 44% | MANOFLAMANCHA | 13 | "The Impossible Dream" show that won the 1966 Tony for Best Musical (4 wds.) |
| 44% | DAMNYANKEES | 11 | "Whatever Lola Wants" show that won the 1956 Tony for Best Musical (2 wds.) |
| 40% | THEBANDSVISIT | 13 | Broadway show by 40-Across starring 18-Across and Tony Shalhoub that won 10 2018 Tony Awards, including Best Musical (3 wds.) |
| 39% | HELLODOLLY | 10 | Broadway show for which 30-Across won the 1964 Tony Award for Best Actress in a Musical (2 wds.) |
| 38% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 37% | LETSMAKELOVE | 12 | Duet by Faith Hill and Tim McGraw, released in 2000, that won the couple a Grammy for Best Country Collaboration with Vocals: 3 wds. |
| 36% | KISSMEKATE | 10 | Cole Porter show that won the 1949 Tony Award for Best Musical |
| 36% | DURURAN | 7 | Group that won the first Grammy for Best Music Video |
| 35% | ZACBROWNBAND | 12 | American country music band with the hit song "Colder Weather", that won the 2010 Grammy for Best New Artist: 3 wds. |
| 34% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 34% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 33% | WEFOUNDLOVE | 11 | Rihanna hit that won the 2013 Best Music Video Grammy: 3 wds. |
| 33% | THEAMERICANS | 12 | Spy drama starring 17-Across and 41-Across that won the 2019 Golden Globe Award for Best Television Series - Drama (2 wds.) |
| 33% | DOLLYPARTON | 11 | "Jolene" singer who wrote the music and lyrics for the Broadway musical "9 to 5": 2 wds. |
| 33% | 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. |
| 33% | BOOMBOOMPOW | 11 | Black Eyed Peas hit that won the 2010 Best Music Video Grammy: 3 wds. |
| 33% | SANTINO | 7 | With 38-Across, "Tootsie" actor who won the 2019 Tony Award for Best Performance by a Leading Actor in a Musical |
| 33% | SARABAREILLES | 13 | "Love Song" singer who wrote the music and lyrics for the Broadway musical "Waitress": 2 wds. |
| 32% | HOME | 4 | "Fun ___," Broadway play with the first female writing team to win the Tony Award for Best Score |
| 32% | WAITRESS | 8 | Broadway musical written by 31-Across that was nominated for four Tony Awards and a Grammy Award |
| 32% | ASONG | 5 | "Sunrise: ___ of Two Humans," 1927 silent romantic drama that won the first Academy Award for Best Cinematography in 1929: 2 wds. |
| 32% | BOBMACKIE | 9 | "The Cher Show" costumer who won the 2019 Tony Award for Best Costume Design in a Musical (2 wds.) |
| 32% | GREENBOOK | 9 | American comedy-drama film that won the 2019 Golden Globe Award for Best Motion Picture - Musical or Comedy: 2 wds. |
| 32% | TOHELLWITHIT | 12 | 2021 mixtape by 16-Across that with the hit singles "Just for Me," "Pain," "Passion," and 26-Across (4 wds.) |
| 32% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |