| 100% | UNFORGETTABLE | 13 | 1991 duet between 18- and 43-Across that won a Grammy |
| 40% | 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.) |
| 40% | IFIAINTGOTYOU | 13 | 2004 18-Across hit that won a Grammy for Best Female R&B Vocal Performance: 5 wds. |
| 40% | GIRLONFIRE | 10 | Album by 40-Across that won a Grammy for Best R&B Album (3 wds.) |
| 39% | IFIAINTGOTYOU | 13 | Song by 40-Across that won a Grammy for Best Female R&B Vocal Performance (5 wds.) |
| 38% | CRANESINTHESKY | 14 | Song by 49-Across that won a Grammy Award for Best R&B Performance in 2017 (4 wds.) |
| 38% | TIGHTENUP | 9 | 27-Across song that won a Grammy Award in 2011 (2 wds.) |
| 37% | FLORIDAPEARL | 12 | Horse that won the Hennessy Cognac Gold Cup at Leopardstown a record four times between 1999 and 2004 |
| 37% | FLORIDA | 7 | & 11A Horse that won the Hennessy Gold Cup at Leopardstown a record four times between 1999 and 2004 |
| 37% | TLC | 3 | R&B group that won a Grammy for "No Scrubs" |
| 37% | WEAREINLOVE | 11 | 33-Across album that won a Grammy for Best Jazz Vocal Performance, Male (4 wds.) |
| 36% | UNAPOLOGETIC | 12 | Seventh studio album by Rihanna, that won her a Grammy in 2014 and had global hits like "Diamonds" and "Stay" |
| 36% | BEATIT | 6 | 1983 hit that won a Grammy for Record of the Year |
| 36% | REHAB | 5 | Amy Winehouse track that won a Song of the Year Grammy |
| 36% | ACDC | 4 | Australian hard rock band that won a Grammy for "War Machine" |
| 36% | CHICAGO | 7 | & 1A Basketball team that won the NBA Finals three times in a row twice, from 1991-93 and 1996-98 |
| 36% | SONGSIHEARD | 11 | 33-Across album that won a Grammy Award for Best Traditional Pop Vocal Album (3 wds.) |
| 36% | PLATINUM | 8 | County album by Miranda Lambert that won a Grammy Award in 2015 |
| 36% | OKGO | 4 | "Here It Goes Again" band that won a 2007 Grammy |
| 36% | GOLD | 4 | ___ Glove (award won a combined 16 times by 18-Across and 42-Across) |
| 36% | BOYGENIUS | 9 | Indie rock supergroup that won a Grammy for the 2023 album "The Record" |
| 36% | BAHA | 4 | ___ Men (group that won a Grammy Award in 2001 for Best Dance Recording) |
| 35% | SYSTEMOFADOWN | 13 | Group that won a Grammy for 2005's "B.Y.O.B": 4 wds. |
| 35% | OWN | 3 | "___ the Night," country album by Lady Antebellum that won a Grammy Award in 2012 |
| 35% | MAROONED | 8 | 1994 Pink Floyd instrumental track that won a Grammy for Best Rock Instrumental Performance |
| 35% | SMOKEYJOESCAFE | 14 | Broadway revue featuring pop standards that won a 1997 Grammy |
| 35% | ENSENADA | 8 | "The Road to ___," country album by Lyle Lovett that won a Grammy Award in 1997 |
| 35% | PARK | 4 | "Same Trailer, Different ___," country album by Kacey Musgraves that won a Grammy Award in 2014 |
| 35% | SCAR | 4 | "___ Tissue," 1999 single by the Red Hot Chili Peppers that won a Grammy in 2000 |