| 100% | HOME | 4 | "Fun ___," Broadway play with the first female writing team to win the Tony Award for Best Score |
| 50% | MARY | 4 | ___ Martin, first Broadway actress to win a Tony Award for playing someone of the opposite sex |
| 45% | SALESMAN | 8 | "Death of a ___," first ever play to win a Tony Award for Best Production in four different years |
| 43% | PHYLICIARASHAD | 14 | First Black performer to win a Tony Award for Lead Actress in a Play, for "A Raisin in the Sun" in 2004: 2 wds. |
| 42% | LOSEYOURSELF | 12 | First rap track to win the Academy Award for Best Original Song |
| 42% | SIDNEYPOITIER | 13 | First black person to win the Academy Award for Best Actor: 2 wds. |
| 41% | OSBORNE | 7 | John ___, 20th-century English playwright who won the Tony Award for Best Play in 1964 |
| 41% | KISSMEKATE | 10 | 1948 Broadway show, with music and lyrics by 41-Across, that won the first Tony for Best Musical: 3 wds. |
| 41% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 40% | JAMESEARLJONES | 14 | First Black performer to win a Tony Award for Lead Actor in a Play, for "The Great White Hope" in 1969: 3 wds. |
| 40% | SAMMENDES | 9 | "The Ferryman" director who won the Tony Award for Best Direction of a Play in 2019 (2 wds.) |
| 39% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 39% | BRYANCRANSTON | 13 | "Network" actor who won the Tony Award for Best Performance by a Leading Actor in a Play in 2019 (2 wds.) |
| 39% | ELAINEMAY | 9 | "The Waverly Gallery" actress who won the Tony Award for Best Performance by a Leading Actress in a Play in 2019 (2 wds.) |
| 37% | BRYANCRANSTON | 13 | "Breaking Bad" actor who won two Tony Awards for Best Actor in a Play, for "All the Way" and "Network" (2 wds.) |
| 37% | 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.) |
| 36% | TONY | 4 | Broadway award that Elton John won for Best Original Score for the musical "Aida" |
| 36% | CARDI | 5 | ___ B, hip hop star who became the first female rapper to win a Grammy for Best Rap Album |
| 36% | MAURICEJARRE | 12 | French conductor and composer who won an Academy Award for Best Original Score for the 1984 movie "A Passage to India" (2 wds.) |
| 36% | JENNIFER | 8 | With 44-Across, actress who won an Emmy Award for playing Tanya McQuoid on the first season of "The White Lotus" |
| 36% | HUMMEL | 6 | "The Basic Training of Pavlo ___," 1977 play starring Al Pacino for which he won a Tony Award for Best Actor |
| 35% | STEPHENDALDRY | 13 | "The Inheritance" director who won the 2020 Tony Award for Best Direction of a Play (2 wds.) |
| 35% | DAVIDYAZBEK | 11 | 30-Across writer/composer who won the 2018 Tony Award for Best Original Score (2 wds.) |
| 35% | SUTTON | 6 | Broadway star Foster who won two Tony Awards for Best Actress in a Musical |
| 35% | FRANKLANGELLA | 13 | "The Americans" actor who won two Tony Awards for Best Actor in a Play, for "Frost/Nixon" and "The Father" (2 wds.) |
| 35% | HELLODOLLY | 10 | Broadway show for which 30-Across won the 1964 Tony Award for Best Actress in a Musical (2 wds.) |
| 35% | LEHMAN | 6 | "The ___ Trilogy," stage play which won Tony Awards for Best Play, Best Actor, and Best Director in 2022 |
| 35% | CHLOEZHAO | 9 | 16-Across director who won an Academy Award for Best Director in 2021, becoming the first non-white woman to win a directing Oscar (2 wds.) |
| 35% | NICKI | 5 | With 33-Across, "Anaconda" rapper who won the BET Award for Best New Artist in 2010 |
| 34% | IAMACAMERA | 10 | Play for which Julie Harris won the 1952 Tony for Best Actress |