| 100% | MUSICVIDEO | 10 | Grammy category won twice each by Taylor Swift, Beyoncé and Johnny Cash |
| 40% | 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.) |
| 36% | FOLKLORE | 8 | Album by Taylor Swift which won the Grammy for Album of the Year in 2021 |
| 34% | TEN | 3 | Number of Grammy Awards won by Taylor Swift |
| 32% | BESTRAPALBUM | 12 | Grammy category won five times by Eminem |
| 32% | BESTRAPPERFORMANCE | 18 | Grammy category won multiple times by Kendrick Lamar |
| 31% | HAS | 3 | "Everything ___ Changed," duet by Taylor Swift and Ed Sheeran |
| 31% | HAS | 3 | "Everything ___ Changed," song by Taylor Swift and Ed Sheeran |
| 31% | BESTGOSPELALBUM | 15 | Grammy Award won twice by CeCe Winans |
| 31% | END | 3 | "___ Game" (song by Taylor Swift featuring Ed Sheeran and Future |
| 31% | CATLADY | 7 | Stereotype embraced by Taylor Swift and Angela from The Office |
| 31% | LOVESTORY | 9 | Taylor Swift song inspired by "Romeo and Juliet" |
| 30% | FOLKLORE | 8 | 2020 album by Taylor Swift featuring the hits "August" and "Cardigan" |
| 30% | 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. |
| 30% | BESTPOPALBUM | 12 | Award won twice by Adele and Kelly Clarkson |
| 30% | SPEAK | 5 | "___ Now," 2010 album by Taylor Swift featuring the hits "Mine" and "Sparks Fly" |
| 29% | SONGOFTHEYEAR | 13 | One of the two Grammy categories won by 31-Across in 2013: 4 wds. |
| 29% | BESTNEWARTIST | 13 | One of the two Grammy categories won by 31-Across in 2013: 3 wds. |
| 29% | ABOYNAMEDSUE | 12 | Johnny Cash song for which Shel Silverstein won a Grammy: 4 wds. |
| 29% | LOVER | 5 | 2019 album by Taylor Swift featuring the hits "Me!" and "You Need to Calm Down" |
| 28% | RECORDOFTHEYEAR | 15 | Grammy award won by "Hello," "Get Lucky" and "Beat It" |
| 28% | BLOOD | 5 | "Bad ___," song by Taylor Swift that won an MTV VMA for Video of the Year in 2015 |
| 28% | BLOOD | 5 | "Bad ___," song by Taylor Swift whose music video features an ensemble cast including Cindy Crawford and Zendaya |
| 28% | HURT | 4 | Original song by Nine Inch Nails that was covered by Johnny Cash in 2002 and won the Grammy for Best Short Form Music Video |
| 28% | CALMDOWN | 8 | "You Need to ___," 2019 song by Taylor Swift which won the MTV Video of the Year: 2 wds. |
| 27% | BAD | 3 | With 35-Across, Taylor Swift hit that won the 2016 Best Music Video Grammy |
| 27% | DOWN | 4 | --> ____" by Taylor Swift |
| 26% | VOCAL | 5 | Best Pop ___ Album (Grammy category won by Dua Lipa in 2021) |
| 26% | BAD | 3 | "___ Blood," song by Taylor Swift |
| 26% | ALLTOOWELL | 10 | Power ballad by Taylor Swift |