| 100% | HADESTOWN | 9 | Anaïs Mitchell work based on Orpheus and Eurydice that won the 2019 Tony Award for Best Musical |
| 44% | KISSMEKATE | 10 | Cole Porter show that won the 1949 Tony Award for Best Musical |
| 43% | SANTINO | 7 | With 38-Across, "Tootsie" actor who won the 2019 Tony Award for Best Performance by a Leading Actor in a Musical |
| 42% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 42% | BOBMACKIE | 9 | "The Cher Show" costumer who won the 2019 Tony Award for Best Costume Design in a Musical (2 wds.) |
| 40% | GREENBOOK | 9 | American comedy-drama film that won the 2019 Golden Globe Award for Best Motion Picture - Musical or Comedy: 2 wds. |
| 38% | SPINNINGSILVER | 14 | 2019 Locus Award for Best Fantasy Novel winner by 27-Across that's loosely based on the tale of "Rumpelstiltskin" (2 wds.) |
| 38% | JERSEYBOYS | 10 | 2006 Tony Award Best Musical winner based on the story of Frankie Valli and the Four Seasons |
| 36% | THE | 3 | "___ Americans," FX show that won the 2019 Golden Globe Award for Best Television Series in Drama |
| 36% | DUNE | 4 | Frank Herbert work that won the inaugural Nebula Award for Best Novel |
| 35% | MIGOS | 5 | "Culture II" hip hop group that won the 2019 BET Award for Best Group |
| 34% | LOESSER | 7 | Frank —, winner of the 1951 Tony Award for Best Musical for Guys and Dolls |
| 34% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 34% | FUNHOME | 7 | Show based on an Alison Bechdel memoir that got the Best Musical Tony |
| 34% | 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% | IGOR | 4 | Tyler, the Creator work that won the 2019 Grammy for Best Rap Album |
| 33% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 33% | LOESSER | 7 | Frank —, 1951 Tony Award for Best Musical winner for Guys and Dolls |
| 33% | AVENUEQ | 7 | Winner of the 2004 Tony Award for Best Musical |
| 33% | KATRINALENK | 11 | 30-Across singer/actress who won the 2018 Tony Award for Best Actress in a Musical (2 wds.) |
| 33% | MANOFLAMANCHA | 13 | "The Impossible Dream" show that won the 1966 Tony for Best Musical (4 wds.) |
| 33% | STRANGERTHINGS | 14 | Netflix horror series that won the People's Choice Awards for the Show of 2019 and the Drama Show of 2019 (2 wds.) |
| 32% | DANNYBURSTEIN | 13 | "Moulin Rouge!" actor who won the 2020 Tony Award for Best Performance by a Featured Actor in a Musical (2 wds.) |
| 32% | CHRISTIANBALE | 13 | Actor who won the 2019 Golden Globe Award for Best Actor in a Motion Picture - Musical or Comedy, for the film "Vice": 2 wds. |
| 32% | DAMNYANKEES | 11 | "Whatever Lola Wants" show that won the 1956 Tony for Best Musical (2 wds.) |
| 32% | THEAMERICANS | 12 | Spy drama starring 17-Across and 41-Across that won the 2019 Golden Globe Award for Best Television Series - Drama (2 wds.) |
| 32% | HELLODOLLY | 10 | Broadway show for which 30-Across won the 1964 Tony Award for Best Actress in a Musical (2 wds.) |
| 32% | ASBRAVEASYOU | 12 | 29-Across novel that won the Kirkus Prize in 2016 and the NAACP Image Award for Outstanding Literary Work for Youth/Teen in 2017 (4 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. |
| 31% | BUTTERFLIES | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Solo Performance |