| 100% | AJA | 3 | 1978 Album of the Year Grammy nominee that features "Josie" and "Peg" |
| 52% | MONAE | 5 | 2019 Album of the Year Grammy nominee, for “Dirty Computer” |
| 44% | MUSGRAVES | 9 | Album of the Year Grammy winner for Golden Hour |
| 43% | EMINEM | 6 | Record of the Year Grammy nominee for "Lose Yourself" |
| 43% | RAITT | 5 | 1989 Album of the Year Grammy winner, for “Nick of Time” |
| 42% | THRILLER | 8 | Album by Michael Jackson and Quincy Jones that won the Grammy for Album of the Year in 1984 |
| 41% | ONO | 3 | Grammy Album of the Year sharer (1982) |
| 41% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 41% | ADELE | 5 | She won Album of the Year honors in 2012 and 2017 |
| 40% | MILEYCYRUS | 10 | "Flowers" Record of the Year Grammy nominee who was born on November 23, 1992 (2 wds.) |
| 39% | DENG | 4 | Time's Man of the Year for 1978 and 1985 |
| 39% | UNFORGETTABLE | 13 | Song of the Year Grammy winner (1992) sung by Nat King Cole and Natalie Cole |
| 39% | CAPOT | 5 | Horse of the Year that won the 1949 Preakness and Belmont |
| 38% | BEYONCE | 7 | Grammy's Album of the Year winner for 2024's "Cowboy Carter" |
| 38% | HUBIE | 5 | Brown who was NBA Coach of the Year in 1978 and 2004 |
| 38% | BEY | 3 | Nickname of 2025's Album of the Year Grammy winner |
| 38% | GETLUCKY | 8 | 2013 Record of the Year Grammy winner by Daft Punk featuring 15-Across/52-Across (2 wds.) |
| 38% | ABOUT | 5 | "All ___ That Bass," 2015 Grammy Song of the Year nominee |
| 38% | HER | 3 | Singer nominated for Album of the Year Grammys in 2019 and 2020 (and whose name spells a pronoun) |
| 38% | SOUND | 5 | With 5- and 1-Down, 2015 Album of the Year nominee by Alabama Shakes |
| 37% | BEYONCE | 7 | Singer who won the Album of the Year Grammy for "Cowboy Carter" |
| 37% | BECK | 4 | Artist who won the 2014 Album of the Year Grammy |
| 36% | HELLO | 5 | Adele song that won Record of the Year and Song of the Year Grammy Awards |
| 36% | BABEL | 5 | 2012 Mumford & Sons album that won the 2013 Grammy for Album of the Year |
| 36% | FAMILY | 6 | "___ Guy," animated TV series that features Queen's album "News of the World" |
| 36% | SKATEPARK | 9 | Olympic arena that features the ends of 17-, 25-, 41-, and 52-Across |
| 36% | ADELE | 5 | British singer who won the Album of the Year Grammy in 2012 for "21" |
| 36% | BECK | 4 | His "Morning Phase" won the Album of the Year Grammy in February 2015 |
| 35% | BEBO | 4 | Social networking site of the '00s that was known for its skin and Lifestream features |
| 35% | PRIME | 5 | The best years of your life, and a word that rhymes with "time" |