| 100% | VOCAL | 5 | Best Pop ___ Album (Grammy Award that Adele won for "21" and "25") |
| 57% | SOUR | 4 | Album by Olivia Rodrigo that won the Grammy Award for Best Pop Vocal Album in 2022 |
| 55% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 49% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |
| 49% | THERESISTANCE | 13 | Muse album that won the 2011 Grammy Award for Best Rock Album: 2 wds. |
| 48% | CHAINOFFOOLS | 12 | Aretha Franklin's 1967 single that won her a Grammy for Best Female R&B Vocal Performance and later a Grammy Hall Of Fame Award: 3 wds. |
| 48% | WASTINGLIGHT | 12 | Foo Fighters album that won the 2012 Grammy Award for Best Rock Album: 2 wds. |
| 48% | OSCAR | 5 | Hollywood award that Elton John won twice for Best Original Song, in 1994 and 2019 |
| 47% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 47% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 46% | OPUS | 4 | Marc Anthony release that won the 2020 Grammy for Best Tropical Latin Album |
| 46% | CLUB | 4 | Culture ___, English pop group that won the Grammy for Best New Artist in 1984 |
| 46% | ERICA | 5 | Singer Campbell who won a Best Gospel Album Grammy Award for "Help" |
| 45% | WEAREINLOVE | 11 | 33-Across album that won a Grammy for Best Jazz Vocal Performance, Male (4 wds.) |
| 45% | CELINEDION | 10 | Singer whose 1996 album "Falling into You" won Grammy Awards for Album of the Year and Best Pop Album (2 wds.) |
| 45% | THRILLER | 8 | Album by Michael Jackson and Quincy Jones that won the Grammy for Album of the Year in 1984 |
| 45% | NOMADLAND | 9 | 50-Across film that won Academy Awards in 2021 for Best Picture, Best Actress, and Best Director |
| 45% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 44% | HADESTOWN | 9 | Anaïs Mitchell work based on Orpheus and Eurydice that won the 2019 Tony Award for Best Musical |
| 44% | TRUTH | 5 | "___ Hurts," song by Lizzo that won the Grammy Award for Best Pop Solo Performance in 2020 |
| 44% | ROLLING | 7 | With 18-Across, Adele single from the album "21" that won the Grammy Award for Record of the Year for 2011 |
| 43% | MUSE | 4 | English band that won a Best Rock Album Grammy for 2015's "Drones" |
| 43% | KISSMEMORE | 10 | 50-Across and SZA hit single that won Best Pop Duo/Group Performance at the 2022 Grammy Awards (3 wds.) |
| 43% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 43% | AMERICANIDIOT | 13 | 2004 Green Day album that won a Best Rock Album Grammy Award (2 wds.) |
| 43% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 43% | ENYA | 4 | Singer who won a Best New Age Album Grammy Award for "Amarantine" |
| 43% | COME | 4 | "The Best is Yet to ___," album by Ella Fitzgerald that won her the Grammy for Best Jazz Vocal Performance in 1984 |
| 42% | EASYONME | 8 | Song Adele won best solo performance Grammy for |
| 42% | THEAMERICANS | 12 | Spy drama starring 17-Across and 41-Across that won the 2019 Golden Globe Award for Best Television Series - Drama (2 wds.) |