| 100% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 78% | LONELYBOY | 9 | 27-Across song that won two Grammy Awards in 2013 (2 wds.) |
| 64% | AINTITFUN | 9 | Hit single by Paramore that won a Grammy Award for Best Rock Song in 2015 (3 wds.) |
| 64% | TAKINGTHE | 9 | "___ Long Way," country album by The Chicks that won a Grammy Award in 2007: 2 wds. |
| 63% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 61% | STAYHIGH | 8 | Brittany Howard song that won the Grammy Award for Best Rock Song in 2021: 2 wds. |
| 59% | THISLAND | 8 | Gary Clark Jr. song that won the Grammy Award for Best Rock Song in 2020: 2 wds. |
| 55% | LITTLEBIG | 9 | ___ Town, country music group that won a Grammy for their hit song "Girl Crush": 2 wds. |
| 55% | BADGUY | 6 | 2019 song by Billie Eilish that won the Grammy Award for Record of the Year in 2020: 2 wds. |
| 54% | TRUTHHURTS | 10 | Viral 46-Across song that won the 2020 Grammy Award for Best Pop Solo Performance (2 wds.) |
| 53% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 53% | PLATINUM | 8 | County album by Miranda Lambert that won a Grammy Award in 2015 |
| 53% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 53% | BAHA | 4 | ___ Men (group that won a Grammy Award in 2001 for Best Dance Recording) |
| 53% | BEAUTIFULLIAR | 13 | Beyoncé and 36-Across song that won an MTV Video Music Award for Most Earthshattering Collaboration in 2007 (2 wds.) |
| 52% | MYWORLD | 7 | "Come into ___," hit song by Australian singer Kylie Minogue which won a Grammy Award in 2004: 2 wds. |
| 52% | THERESISTANCE | 13 | Muse album that won the 2011 Grammy Award for Best Rock Album: 2 wds. |
| 52% | OWN | 3 | "___ the Night," country album by Lady Antebellum that won a Grammy Award in 2012 |
| 52% | ENSENADA | 8 | "The Road to ___," country album by Lyle Lovett that won a Grammy Award in 1997 |
| 52% | PARK | 4 | "Same Trailer, Different ___," country album by Kacey Musgraves that won a Grammy Award in 2014 |
| 52% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 51% | TIFFANYHADDISH | 14 | "Black Mitzvah" comedian who won a Grammy Award for Best Comedy Album in 2021 (2 wds.) |
| 51% | KATHYGRIFFIN | 12 | "Calm Down Gurrl" comedian who won a Grammy Award for Best Comedy Album in 2014 (2 wds.) |
| 51% | WHOOPIGOLDBERG | 14 | "Direct from Broadway" comedian who won a Grammy Award for Best Comedy Album in 1986 (2 wds.) |
| 51% | IMNOT | 5 | With 49-Across, song that won 14-Across his Best Country Song Grammy: 2 wds. |
| 51% | BRITNEYSPEARS | 13 | Former "All New Mickey Mouse Club" Mouseketeer who won a Grammy Award for her song "Toxic" (2 wds.) |
| 50% | AMERICANIDIOT | 13 | 2004 Green Day album that won a Best Rock Album Grammy Award (2 wds.) |
| 50% | HOLIDAYINN | 10 | 1942 film that won a Best Original Song Oscar for 34-Across: 2 wds. |
| 50% | GEORGSOLTI | 10 | Hungarian-British artist who holds the record for the most Grammy Awards won in a lifetime, with 31: 2 wds. |
| 50% | DOUBLEFANTASY | 13 | 42-Across album that received a Grammy Award: 2 wds. |