| 100% | SOLONGSOWRONG | 13 | Grammy-winning album by 39-Across and 18-Across (4 wds.) |
| 67% | MYSONGS | 7 | 2019 remix and greatest hits album by 39-Across featuring 18-Across and 25-Across (2 wds.) |
| 64% | SONGSINAMINOR | 13 | 2001 Grammy-winning album by 42-Across with the singles "Fallin'" and "A Woman's Worth" (4 wds.) |
| 63% | DOESHELOVEYOU | 13 | Grammy-winning song re-recorded by Dolly Parton and 43-Across for 18-Across (4 wds.) |
| 61% | GIRLONFIRE | 10 | Grammy-winning album by 42-Across with the singles "Brand New Me" and "New Day" (3 wds.) |
| 60% | KINGDOMCOME | 11 | Grammy-nominated 2006 album by 39-Across (2 wds.) |
| 59% | THEHEIST | 8 | Debut album by 18-Across and Ryan Lewis: 2 wds. |
| 58% | KILLINTIME | 10 | Album by 45-Across featuring the singles 18-Across and 26-Across that won the 1989 Album of the Year Academy of Country Music Award (2 wds.) |
| 57% | WEAREINLOVE | 11 | Grammy-winning 1990 album by 33-Across (4 wds.) |
| 57% | COMEAWAYWITHME | 14 | Grammy-winning debut album by 52-Across (4 wds.) |
| 56% | RAISINGSAND | 11 | Bluegrass album by Robert Plant and Alison Krauss that won Album of the Year at the 2009 Grammy Awards (2 wds.) |
| 56% | BESTFOLKALBUM | 13 | 2012 Grammy won by 44-Across for 18-Across: 3 wds. |
| 55% | BARKATTHEMOON | 13 | 1983 solo album by 39-Across (4 wds.) |
| 55% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 55% | SILVERSLUGGER | 13 | Batting award won four times by 17-Across and once by 39-Across: 2 wds. |
| 53% | MYEVERYTHING | 12 | 2014 album by 18-Across with the hit singles "Problem" and "Break Free": 2 wds. |
| 53% | REBELDIAMONDS | 13 | 2023 greatest hits album by 42-Across that includes "Mr. Brightside" and 18-Across (2 wds.) |
| 53% | SONGOFTHEYEAR | 13 | One of the two Grammy categories won by 31-Across in 2013: 4 wds. |
| 52% | NEWKIDINTOWN | 12 | Grammy-winning song by the Eagles which was the first single from the same album as 15a: 4 wds. |
| 52% | HARMONYHALL | 11 | Hit single on the 2019 Grammy-winning album by 33-Across (2 wds.) |
| 52% | ITISWHATITIS | 12 | Album by 41-Across featuring 17-Across that won the Grammy Award for Best Progressive R&B Album in 2021 (5 wds.) |
| 52% | SONGSIHEARD | 11 | Grammy-winning 2001 album by 33-Across (3 wds.) |
| 51% | THELADYKILLER | 13 | 2010 album by 39-Across: 3 wds. |
| 51% | ONTHEROADAGAIN | 14 | Song by 30-Across/33-Across that won a Grammy Award for Best Country Song and was inducted into the Grammy Hall of Fame (4 wds.) |
| 51% | SHADOWTYRANTS | 13 | 2018 novel in the Oregon Files series by 18-Across and 39-Across (2 wds.) |
| 50% | KISSMEKATE | 10 | 1948 show with music and lyrics by 39-Across that won the first Tony Award for Best Musical (3 wds.) |
| 50% | MYAIMISTRUE | 11 | 1977 album by 31-Across: 4 wds. |
| 50% | AMERICANGODS | 12 | Novel by 39-Across that won the Hugo Award for Best Novel and the Nebula Award for Best Novel (2 wds.) |
| 50% | THEWEEKND | 9 | 16-Across and 34-Across singer who won the 2018 Best Urban Contemporary Album Grammy for "Starboy" (2 wds.) |
| 49% | ALMACARIBENA | 12 | Grammy-winning album of traditional tropical Latin music by 30-Across (2 wds.) |