| 100% | RANDB | 5 | Grammy category for 49-Across (3 wds.) |
| 62% | LAWYERSINLOVE | 13 | 1983 hit for 49-Across that satirized 1980s materialism: 3 wds. |
| 58% | BESTNEWARTIST | 13 | One of the two Grammy categories won by 31-Across in 2013: 3 wds. |
| 54% | FOOLFORYOU | 10 | Best R&B Song Grammy winner for 39-Across: 3 wds. |
| 53% | ONTHEMAP | 8 | "Wheel of Fortune" category for FRESNO CALIFORNIA: 3 wds. |
| 52% | BESTNEWARTIST | 13 | Category of 43-Across's first Grammy Award (3 wds.) |
| 50% | RAP | 3 | Grammy category for Eminem |
| 46% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 45% | RAP | 3 | Grammy category ... or 3-Down backwards |
| 45% | SOMEBODYSBABY | 13 | 1982 hit for 49-Across that appeared in "Fast Times at Ridgemont High": 2 wds. |
| 45% | WHOFEARSDEATH | 13 | 2011 World Fantasy Award for Best Novel winner by 49-Across (3 wds.) |
| 45% | PRINCEHAMLET | 12 | Shakespearean Tony-winning stage role for 49-Across (2 wds.) |
| 45% | YOULLTHINKOFME | 14 | First song by 49-Across to win the Grammy Award for Best Male Country Vocal Performance (4 wds.) |
| 44% | SONGOFTHEYEAR | 13 | One of the two Grammy categories won by 31-Across in 2013: 4 wds. |
| 44% | BESTFOLKALBUM | 13 | 2012 Grammy won by 44-Across for 18-Across: 3 wds. |
| 44% | JANETHEVIRGIN | 13 | The CW dramedy starring 49-Across (3 wds.) |
| 44% | BRASSINPOCKET | 13 | 1980 hit for 15-Across: 3 wds. |
| 43% | WHATMAKES | 9 | With 17- and 49-Across, 2011 debut single for One Direction: 2 wds. |
| 43% | III | 3 | 3, for ancient 1 Across |
| 42% | IMNOT | 5 | With 49-Across, song that won 14-Across his Best Country Song Grammy: 2 wds. |
| 42% | BESTDISCO | 9 | With 36-Across, Grammy category that was only awarded in 1980 (2 wds.) |
| 42% | THEBOOKTHIEF | 12 | 2013 film for which 46-Across won a Grammy Award (3 wds.) |
| 41% | LUCKYYOU | 8 | 37-Across song nominated for the 2019 Best Rap Song Grammy Award (2 wds.) |
| 41% | SAMENAME | 8 | "Wheel of Fortune" category for FLOWER & TASTE BUDS: 2 wds. |
| 41% | CLASSICTV | 9 | "Wheel of Fortune" category for FATHER KNOWS BEST: 2 wds. |
| 41% | YAFICTION | 9 | Bookstore shelving category for "The Hunger Games": 2 wds., abbr. |
| 40% | ALBUMOFTHEYEAR | 14 | Grammy Award for an outstanding record: 4 wds. |
| 40% | SPACECOWBOY | 11 | Song by 34-Across that won the 2019 Grammy for Best Country Song (2 wds.) |
| 40% | LOVESONG | 8 | Top 10 single by 31-Across that was nominated for two Grammy Awards (2 wds.) |
| 40% | WEAREINLOVE | 11 | 33-Across album that won a Grammy for Best Jazz Vocal Performance, Male (4 wds.) |