| 100% | HIRT | 4 | Grammy-winning “Java” trumpeter Al |
| 85% | HIRT | 4 | Grammy-winning trumpeter Al |
| 72% | HIRT | 4 | "Java" trumpeter Al |
| 66% | YANKOVIC | 8 | Grammy-winning satirical artist Al |
| 65% | EATIT | 5 | Grammy-winning "Weird Al" song |
| 63% | EATIT | 5 | Grammy-winning Weird Al Yankovic song |
| 61% | YANKOVIC | 8 | "Weird Al" ___, comedian who won three Grammy awards for his comedy albums |
| 60% | MARSALIS | 8 | Grammy- and Pulitzer-winning trumpeter Wynton |
| 60% | HIRT | 4 | Trumpeter Al |
| 59% | HAM | 3 | Meat mentioned in "Weird Al" Yankovic's "Fat", whose video won a Grammy Award |
| 57% | WEIRDAL | 7 | Grammy winning parody singer |
| 56% | HIRT | 4 | Trumpeter Al from 55-Across |
| 56% | ADELE | 5 | Grammy winning singer of "Hello" |
| 56% | HIRT | 4 | Jazz trumpeter Al |
| 53% | ELTON | 5 | John with five Grammy wins |
| 53% | LINDA | 5 | Ronstadt with 10 Grammy wins |
| 53% | ALICIA | 6 | Keys with 16 Grammy wins |
| 52% | HIRT | 4 | “Honey in the Horn” trumpeter Al |
| 52% | EATIT | 5 | Grammy-winning Weird Al parody whose first verse mentions Cap'n Crunch and Raisin Bran |
| 51% | BELA | 4 | Banjoist Fleck with 18 Grammy wins |
| 50% | CHETS | 5 | Jazz trumpeter Baker et al. |
| 48% | UNSER | 5 | Al who won four Indy 500s |
| 48% | RAVI | 4 | ___ Shankar, Grammy winning artist and father of Norah Jones |
| 47% | BESTRAPALBUM | 12 | Grammy category won five times by Eminem |
| 47% | BESTGOSPELALBUM | 15 | Grammy Award won twice by CeCe Winans |
| 46% | EIGHT | 5 | Number of Grammy wins for Ziggy Marley or Stephen Marley |
| 46% | BESTRAPPERFORMANCE | 18 | Grammy category won multiple times by Kendrick Lamar |
| 45% | BESTFOLKALBUM | 13 | 2012 Grammy won by 44-Across for 18-Across: 3 wds. |
| 45% | DIERKS | 6 | Grammy-nominated country crooner Bentley (14 nods, 0 wins) |
| 44% | MILES | 5 | Great Jazz trumpeter __ Davis won 9 grammys |