| 100% | EGOT | 4 | Set of awards won by John Legend and Rita Moreno, for short |
| 63% | EGOT | 4 | "Grand slam" of awards won by John Legend, for short |
| 60% | EGOT | 4 | Quartet of awards earned by John Legend and Whoopi Goldberg, for short |
| 58% | EGOT | 4 | "Grand slam" of awards earned by John Legend and Jennifer Hudson, for short |
| 52% | EGOT | 4 | "Grand slam" of awards won by Elton John, for short |
| 46% | EGOT | 4 | "Grand slam" of awards won by Jennifer Hudson, for short |
| 45% | EGOT | 4 | Quartet of awards won by Whoopi Goldberg, for short |
| 39% | EGOT | 4 | "Grand slam" of awards earned by Viola Davis and Jennifer Hudson, for short |
| 37% | OSCARS | 6 | Awards won by Mahershala Ali for “Moonlight” and “Green Book” |
| 36% | ESPY | 4 | Award won by Tom Brady for "Best NFL Player" and "Best Male Athlete" |
| 35% | EGOT | 4 | Complete set of showbiz awards, for short |
| 35% | MANBOOKERPRIZE | 14 | Award won by Marlon James, in 2015, for “A Brief History of Seven Killings” |
| 34% | BESTMUSICAL | 11 | Award won by the starts of 17-, 25-, 39- and 52-Across and 11- and 29-Down |
| 34% | FOUR | 4 | Number of Emmy Awards for acting won by both Bryan Cranston and Dennis Franz |
| 33% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 33% | OED | 3 | Set of books once awarded to winners of Britain's "Countdown" game show, for short |
| 33% | EGOT | 4 | Award quartet won by 31-Across, for short |
| 33% | 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.) |
| 33% | EGOT | 4 | Award quartet for John Legend, for short |
| 32% | HUGO | 4 | Set of literary awards for science-fiction and fantasy genre which is named after writer-editor Gernsback |
| 32% | BESTKISS | 8 | MTV Movie Award won by Kristen Stewart and Robert Pattinson for four consecutive years |
| 32% | EMMYS | 5 | Awards won this week by John Mulaney and Bill Hader |
| 32% | OBIES | 5 | Pair of awards won by A Strange Loop |
| 32% | XXXXXXXXXXXXXX | 14 | Booze pitched by John Legend and Chelsea Handler |
| 31% | GRAMMY | 6 | Song of the Year award won by Lorde for 36-Across |
| 31% | EMMY | 4 | Award for television excellence...and what each of 7A, 18A, 22A, 38A, and 43D have won |
| 31% | HELLO | 5 | 2015 song by Adele that won the Grammy Award for Record of the Year |
| 31% | DORSEYPRIZES | 12 | Awards won by brother bandleaders Tommy and Jimmy? |
| 31% | TONYS | 5 | Awards won by the musicals "Hamilton" and "Hadestown" |
| 31% | EMMY | 4 | Award won by Quinta Brunson for "Abbott Elementary" |