| 100% | BAD | 3 | With 35-Across, Taylor Swift hit that won the 2016 Best Music Video Grammy |
| 57% | WEFOUNDLOVE | 11 | Rihanna hit that won the 2013 Best Music Video Grammy: 3 wds. |
| 57% | HAPPY | 5 | Pharrell Williams hit that won the 2015 Best Music Video Grammy |
| 55% | BOOMBOOMPOW | 11 | Black Eyed Peas hit that won the 2010 Best Music Video Grammy: 3 wds. |
| 46% | BLANKSPACE | 10 | Taylor Swift song that won the 2015 MTV VMA for Best Female Video: 2 wds. |
| 46% | DURURAN | 7 | Group that won the first Grammy for Best Music Video |
| 41% | ALWAYSONMYMIND | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1983: 4 wds. |
| 41% | ONTHEROADAGAIN | 14 | 28-/40-Across hit that won the Grammy for Best Country Song in 1981: 4 wds. |
| 39% | TRUTHHURTS | 10 | 1-Across hit that won Best Pop Solo Performance at the 2020 Grammy Awards: 2 wds. |
| 39% | BETTERMAN | 9 | 2016 song written by Taylor Swift and performed by 33-Across that won a Grammy Award for Best Country Duo/Group Performance (2 wds.) |
| 39% | RED | 3 | Taylor Swift album with the hit "All Too Well" |
| 39% | ZACBROWNBAND | 12 | American country music band with the hit song "Colder Weather", that won the 2010 Grammy for Best New Artist: 3 wds. |
| 38% | RED | 3 | Taylor Swift's 2012 album with the hit "All Too Well" |
| 37% | WOMANIZER | 9 | 2008 #1 song by 32-Across that won the MTV Video Music Award for Best Pop Video |
| 37% | DONTWANNAFIGHT | 14 | Alabama Shakes song that won the Grammy Award for Best Rock Song in 2016: 3 wds. |
| 37% | SKYSCRAPER | 10 | Top 10 43-Across song that won the 2012 MTV "Best Video with a Message" Video Music Award |
| 36% | FLY | 3 | "Learning to ___," Pink Floyd song that won Best Concept Video at the MTV Video Music Awards |
| 36% | HORSE | 5 | "Dark ___," song by Katy Perry featuring Juicy J that won the MTV Video Music Award for Best Female Video in 2014 |
| 35% | TOPIMPA | 7 | With 48-Across, Kendrick Lamar album that won Best Rap Album at the 2016 Grammys: 3 wds. |
| 35% | BAD | 3 | With 7-Down, Billie Eilish hit that won the 2020 Grammy for Song of the Year |
| 35% | LETSMAKELOVE | 12 | Duet by Faith Hill and Tim McGraw, released in 2000, that won the couple a Grammy for Best Country Collaboration with Vocals: 3 wds. |
| 34% | VAMPIREWEEKEND | 14 | Indie rock band that won a Best Alternative Music Album Grammy in 2020 for "Father of the Bride": 2 wds. |
| 34% | CAROLINA | 8 | With 35-Across, 1969 song about homesickness that's on James Taylor's "Greatest Hits" album |
| 34% | PONTOON | 7 | #1 country hit for 48-Across that won the 2013 Grammy for Best Country Duo/Group Performance |
| 34% | RED | 3 | Taylor Swift album that won two Billboard Music Awards in 2013 |
| 34% | KARMA | 5 | Taylor Swift hit with the lyric “it’s coming back around” |
| 33% | JUSTIN | 6 | With 35-Across, "Yummy" singer who won the Pop Album of the Year Juno in 2011 and 2016 |
| 33% | SHAPE | 5 | With 35-Across, 2017 Ed Sheeran hit that spent 16 weeks at #1 on the Canadian Hot 100 |
| 33% | ISITOVERNOW | 11 | 2023 Taylor Swift hit that debuted at #1 on the Hot 100: 4 wds. |
| 33% | TAKEONME | 8 | A-ha hit that won six MTV Video Music Awards |