| 100% | OBIE | 4 | Award won by "Hamilton" a year before it won the Tony |
| 57% | BESTMUSICAL | 11 | Tony Award won by the starred answers in the years of their clues |
| 52% | BRYANCRANSTON | 13 | "Network" actor who won the Tony Award for Best Performance by a Leading Actor in a Play in 2019 (2 wds.) |
| 51% | 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.) |
| 49% | SANTINO | 7 | With 38-Across, "Tootsie" actor who won the 2019 Tony Award for Best Performance by a Leading Actor in a Musical |
| 49% | DANNYBURSTEIN | 13 | "Moulin Rouge!" actor who won the 2020 Tony Award for Best Performance by a Featured Actor in a Musical (2 wds.) |
| 49% | ARGO | 4 | It won the Best Picture Oscar two years before "Birdman" |
| 49% | AWAY | 4 | "Give It ___," 1991 song by the Red Hot Chili Peppers which won a Grammy Award in 1992 |
| 49% | DAVIDALANGRIER | 14 | "A Soldier's Play" actor who won the 2020 Tony Award for Best Performance by a Featured Actor in a Play (3 wds.) |
| 49% | PRIZES | 6 | Awards won by best books of the years, e.g. Orange |
| 49% | BEST | 4 | ___ Picture (Academy Award won by "12 Years a Slave") |
| 49% | 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.) |
| 48% | ESPY | 4 | Award won by Lance Armstrong in 2005 for the third straight year |
| 48% | GRAMMY | 6 | Song of the Year award won by Lorde for 36-Across |
| 47% | HUGO | 4 | Science fiction award won by N.K. Jemisin three years in a row |
| 46% | TONYS | 5 | Awards won by the musicals "Hamilton" and "Hadestown" |
| 45% | MCCOY | 5 | Tony —, jockey who won the 2010 BBC Sports Personality of the Year award |
| 45% | MVP | 3 | Award won four times in the W.N.B.A. by A'ja Wilson |
| 45% | SAMMENDES | 9 | "The Ferryman" director who won the Tony Award for Best Direction of a Play in 2019 (2 wds.) |
| 44% | OBIE | 4 | Award won by Hamilton in 2015 |
| 44% | BET | 3 | Teyana Taylor won Video Director of the Year at its 2020 award show |
| 44% | HELLO | 5 | 2015 song by Adele that won the Grammy Award for Record of the Year |
| 43% | GIRL | 4 | 2019 album by 44-Across that won the Country Music Association's Album of the Year Award |
| 43% | SINGLE | 6 | "___ Ladies (Put a Ring on It)," 2008 song by Beyonce that won three Grammy Awards |
| 43% | STEPHENDALDRY | 13 | "The Inheritance" director who won the 2020 Tony Award for Best Direction of a Play (2 wds.) |
| 43% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 42% | GARTHBROOKS | 11 | "That Girl Is a Cowboy" singer who won the 2019 CMA Award for Entertainer of the Year (2 wds.) |
| 42% | TAYLORSWIFT | 11 | "Shake It Off" singer who won the 2007 CMA New Artist of the Year award: 2 wds. |
| 42% | EMMY | 4 | Award won by a soap, perhaps |
| 42% | OWN | 3 | "___ the Night," country album by Lady Antebellum that won a Grammy Award in 2012 |