| 100% | GRAMMY | 6 | Award won by "DAMN." in the category of Best Rap Album |
| 54% | GRAMMY | 6 | Award notably won in each of the "big four" categories by this puzzle's honoree |
| 54% | SOUR | 4 | Album by Olivia Rodrigo that won the Grammy Award for Best Pop Vocal Album in 2022 |
| 52% | PRIZES | 6 | Awards won by best books of the years, e.g. Orange |
| 51% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 51% | BESTPLAY | 8 | Award won by "The Curious Incident of the Dog in the Night-Time" |
| 50% | BESTMUSICAL | 11 | Tony Award won by the starred answers in the years of their clues |
| 49% | ASLEEP | 6 | "When We All Fall ___, Where Do We Go?," studio album by Billie Eilish that won the Grammy Award for Album of the Year in 2020 |
| 49% | RAP | 3 | Best ___ Album (Grammy Award won by Doechii in 2025) |
| 46% | FOLKLORE | 8 | Album by Taylor Swift which won the Grammy for Album of the Year in 2021 |
| 46% | ROLLING | 7 | "___ in the Deep," hit song by Adele that won 3 Grammy awards including Record of the Year in 2012 |
| 46% | SIGN | 4 | "___ of the Times," hit song by Harry Styles which won a Brit Award in 2018 |
| 45% | THRILLER | 8 | Album by Michael Jackson and Quincy Jones that won the Grammy for Album of the Year in 1984 |
| 45% | OSCAR | 5 | Award won by the director Chloé Zhao in 2021 |
| 45% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 45% | HOUSE | 5 | Harry's ___, album by Harry Styles that won the Grammy Album of the Year in 2023 |
| 45% | JON | 3 | ___ Batiste, "We Are" singer who won the Grammy Award for Album of the Year in 2022 |
| 45% | TAKINGTHE | 9 | "___ Long Way," country album by The Chicks that won a Grammy Award in 2007: 2 wds. |
| 45% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 45% | VOCAL | 5 | Best Pop ___ Album (Grammy category won by Dua Lipa in 2021) |
| 44% | ILLMATIC | 8 | Best rap album of the nineteen-nineties, according to Complex |
| 44% | SAMMENDES | 9 | "The Ferryman" director who won the Tony Award for Best Direction of a Play in 2019 (2 wds.) |
| 44% | ELVISCOSTELLO | 13 | "Look Now" singer who won the Best Traditional Pop Vocal Album Grammy Award in 2020 (2 wds.) |
| 44% | RIHANNA | 7 | One-named singer who won the Grammy Award for Best Urban Contemporary Album for "Unapologetic" in 2014 |
| 44% | MAKING | 6 | "___ a Fire," song by Foo Fighters that won the Grammy Award for Best Rock Performance in 2022 |
| 44% | PDJELICLARK | 11 | Writer whose "A Master of Djinn" won the Nebula Award for Best Novel in 2022 (3 wds.) |
| 44% | HER | 3 | One-named artist whose self-titled album won the Grammy Award for Best R & B album in 2019 |
| 44% | LEAVE | 5 | "___ the Door Open," song by Silk Sonic that won the Grammy Award for Song of the Year in 2022 |
| 44% | IHOPEYOUDANCE | 13 | Song by 29-Across/32-Across that won the Best Country Song Grammy Award in 2001 (4 wds.) |
| 44% | WAITING | 7 | "___ on a War," song by Foo Fighters that won the Grammy Award for Best Rock song in 2022 |