| 100% | DOUBLEFANTASY | 13 | 42-Across album that received a Grammy Award: 2 wds. |
| 59% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 56% | NEEDEDME | 8 | 2016 Rihanna hit that received a Grammy nomination for Best R&B Performance: 2 wds. |
| 55% | MELODRAMA | 9 | 2017 album by 53-Across that received a Grammy Award nomination for Album of the Year |
| 53% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 52% | MORNINGPHASE | 12 | Beck album that won the 2015 Grammy Award for Best Rock Album: 2 wds. |
| 52% | THERESISTANCE | 13 | Muse album that won the 2011 Grammy Award for Best Rock Album: 2 wds. |
| 52% | WASTINGLIGHT | 12 | Foo Fighters album that won the 2012 Grammy Award for Best Rock Album: 2 wds. |
| 51% | TAKINGTHE | 9 | "___ Long Way," country album by The Chicks that won a Grammy Award in 2007: 2 wds. |
| 51% | AMERICANIDIOT | 13 | 2004 Green Day album that won a Best Rock Album Grammy Award (2 wds.) |
| 49% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 49% | KATHYGRIFFIN | 12 | "Calm Down Gurrl" comedian who won a Grammy Award for Best Comedy Album in 2014 (2 wds.) |
| 49% | WHOOPIGOLDBERG | 14 | "Direct from Broadway" comedian who won a Grammy Award for Best Comedy Album in 1986 (2 wds.) |
| 48% | BLANKSPACE | 10 | Second single from Taylor Swift's fifth album, that received three Grammy nominations, and had a part in the lyrics misheard by many: 2 wds. |
| 48% | WEAREINLOVE | 11 | 33-Across album that won a Grammy for Best Jazz Vocal Performance, Male (4 wds.) |
| 48% | CELIACRUZ | 9 | "Queen of Salsa" who received a 2016 Grammy Lifetime Achievement Award: 2 wds. |
| 48% | LINDARONSTADT | 13 | "Queen of Rock" who received a 2016 Grammy Lifetime Achievement Award: 2 wds. |
| 47% | RUTHBROWN | 9 | "Queen of R&B" who received a 2016 Grammy Lifetime Achievement Award: 2 wds. |
| 45% | LIVINGHISTORY | 13 | Memoir by 31-Across whose audiobook version was nominated for a Grammy Award for Best Spoken Word Album (2 wds.) |
| 44% | THOMASPYNCHON | 13 | Novelist who received a National Book Award for "Gravity's Rainbow": 2 wds. |
| 44% | CARLOSSANTANA | 13 | Latin Grammy award winner who teaches a MasterClass course on guitar: 2 wds. |
| 44% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 43% | MYWORLD | 7 | "Come into ___," hit song by Australian singer Kylie Minogue which won a Grammy Award in 2004: 2 wds. |
| 43% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 42% | BETTERNOW | 9 | Top 10 song by 42-Across that was nominated for a Best Pop Solo Performance Grammy Award (2 wds.) |
| 42% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 42% | TIFFANYHADDISH | 14 | "The Last O.G." actress who won a Grammy for Best Comedy Album in 2021: 2 wds. |
| 41% | PORKANDBEANS | 12 | Single by 42-Across whose video won a Grammy Award for Best Music Video in 2009 (3 wds.) |
| 41% | WHITEWEDDING | 12 | 42-Across hit song that plays over a bridal montage in a 1998 Adam Sandler film (2 wds.) |
| 41% | PLATINUM | 8 | County album by Miranda Lambert that won a Grammy Award in 2015 |