| 100% | FOUR | 4 | Number of Emmy Awards for acting won by both Bryan Cranston and Dennis Franz |
| 32% | ISSA | 4 | Rae who won NAACP Image Awards in 2022 for both acting in and writing "Insecure" |
| 31% | EGOT | 4 | Set of awards won by John Legend and Rita Moreno, for short |
| 30% | NINE | 4 | Number of Grammy Awards won by 12-Down |
| 30% | TEN | 3 | Number of Grammy Awards won by Bonnie Raitt |
| 30% | TEN | 3 | Number of Grammy Awards won by Taylor Swift |
| 30% | TEN | 3 | Number of Grammy Awards won by Dolly Parton |
| 30% | NINE | 4 | Number of M.V.P. awards won by Wayne Gretzky |
| 30% | DAYTIME | 7 | ___ Emmy Awards (honors won by soaps and talk shows) |
| 28% | ARCHIEMANNING | 13 | College Football Hall of Famer whose sons Peyton and Eli both won the NFL Man of the Year award named for 18-Across (2 wds.) |
| 28% | EMMY | 4 | Award Bryan Cranston won four times for portraying Walter White |
| 28% | OSCARS | 6 | Awards won by Mahershala Ali for “Moonlight” and “Green Book” |
| 28% | EMMY | 4 | Award for television excellence...and what each of 7A, 18A, 22A, 38A, and 43D have won |
| 27% | ESPY | 4 | Award won by Tom Brady for "Best NFL Player" and "Best Male Athlete" |
| 27% | MANBOOKERPRIZE | 14 | Award won by Marlon James, in 2015, for “A Brief History of Seven Killings” |
| 27% | EGOT | 4 | Quartet of awards earned by John Legend and Whoopi Goldberg, for short |
| 26% | REHAB | 5 | 2008 Grammy Award for Song of the Year and Record of the Year winner by Amy Winehouse |
| 26% | EGOT | 4 | "Grand slam" of awards earned by John Legend and Jennifer Hudson, for short |
| 26% | EGOT | 4 | "Grand slam" of awards earned by Viola Davis and Jennifer Hudson, for short |
| 26% | EGOT | 4 | Quartet of awards won by Whoopi Goldberg, for short |
| 26% | LOVE | 4 | "___ and Marriage," 1956 cover by Frank Sinatra that won an Emmy for Best Musical Contribution |
| 26% | BESTMUSICAL | 11 | Award won by the starts of 17-, 25-, 39- and 52-Across and 11- and 29-Down |
| 25% | ULEE | 4 | Character of a beekeeper played by Peter Fonda for which he won a Golden Globe Award |
| 25% | SNL | 3 | Emmy-winning show of both 1976 and 2017, in brief |
| 25% | SIX | 3 | Number of times Garth Brooks has won the Country Music Association Award for Entertainer of the Year |
| 25% | SELIG | 5 | Josh ___, Daytime Emmy Award-winning writer for Sesame Street, Oobi and Wonder Pets |
| 25% | EGOT | 4 | "Grand slam" of awards won by Jennifer Hudson, for short |
| 25% | EGOT | 4 | "Grand slam" of awards won by Elton John, for short |
| 25% | EGOT | 4 | "Grand slam" of awards won by John Legend, for short |
| 25% | VIJAYSINGH | 10 | Golfer who won both PGA Tour Player of the Year and Rookie of the Year awards: 2 wds. |