| 100% | DIARY | 5 | "The ___ of Alicia Keys" (R&B album that won three Grammy Awards) |
| 52% | ASIAM | 5 | 2007 Alicia Keys album that won three Grammys |
| 51% | BABEL | 5 | 2012 Mumford & Sons album that won the 2013 Grammy for Album of the Year |
| 51% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |
| 51% | THERESISTANCE | 13 | Muse album that won the 2011 Grammy Award for Best Rock Album: 2 wds. |
| 51% | WASTINGLIGHT | 12 | Foo Fighters album that won the 2012 Grammy Award for Best Rock Album: 2 wds. |
| 51% | ANTI | 4 | Rihanna album that won Favorite Soul/R&B Album at the 2016 American Music Awards |
| 50% | HELLO | 5 | Adele hit song that won three Grammy Awards |
| 50% | HELLO | 5 | 2015 Adele song that won three Grammy Awards |
| 50% | FROMTHEFIRES | 12 | Greta Van Fleet album that won the Grammy Award for Best Rock Album in 2019 (3 wds.) |
| 49% | HELLO | 5 | 2015 song by Adele that won the Grammy Award for Record of the Year |
| 49% | HELLO | 5 | Adele song that won Record of the Year and Song of the Year Grammy Awards |
| 49% | REHAB | 5 | 2006 Amy Winehouse hit that won three Grammy Awards in 2008 |
| 48% | PIECEOFME | 9 | Song by 32-Across that won three MTV Video Music Awards in 2008, including Video of the Year (3 wds.) |
| 48% | NAME | 4 | "You Don't Know My ___," 2003 song by Alicia Keys that won a Grammy Award for Best R&B Song |
| 48% | HELLO | 5 | Adele song that won the 2016 Record of the Year and Song of the Year Grammy Awards |
| 47% | HELP | 4 | 1965 Beatles album that was the first rock album nominated for an Album of the Year Grammy Award |
| 47% | 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. |
| 47% | CSO | 3 | Musical gp. that won two Grammy Awards for Riccardo Muti for the recording of "Messa da Requiem" |
| 47% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 47% | IGOR | 4 | Tyler, the Creator album that won Best Rap Album at the 2020 Grammy Awards |
| 47% | SINGLE | 6 | "___ Ladies (Put a Ring on It)," 2008 song by Beyonce that won three Grammy Awards |
| 46% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 46% | HELLO | 5 | Hit song by Adele that won 3 Grammy awards including Record of the Year in 2017 |
| 46% | YANKOVIC | 8 | "Weird Al" ___, comedian who won three Grammy awards for his comedy albums |
| 46% | ROCK | 4 | Chris ___, comedian who has won three Grammy Awards for his comedy albums |
| 45% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 45% | SMOKEYROBINSON | 14 | "I Second That Emotion" singer who won one of the first Grammy Legend Awards, in 1990: 2 wds. |
| 45% | HOST | 4 | Alicia Keys, for the 2019 Grammy Awards |
| 45% | ALJARREAU | 9 | Singer who won Grammy Awards in three different categories (jazz, pop, and R. & B.) |